dual inhibitors of epidermal growth factor receptor and ...s1 dual inhibitors of epidermal growth...
TRANSCRIPT
![Page 1: Dual inhibitors of epidermal growth factor receptor and ...S1 Dual inhibitors of epidermal growth factor receptor and topoisomerase IIα derived from quinoline scaffold Monika Chauhan,a](https://reader034.vdocuments.site/reader034/viewer/2022051902/5ff2a5f8ddeec7176661cd27/html5/thumbnails/1.jpg)
S1
Dual inhibitors of epidermal growth factor receptor and topoisomerase
IIα derived from quinoline scaffold
Monika Chauhan,a Gaurav Joshi,a Harveen Kler, a Archana Kashyap,a Suyog M. Amrutkar,b Uttam Chand Banerjee,b Praveen Sharma,c Sandeep Singh,c Raj Kumar*a
Spectra of representative compounds
Electronic Supplementary Material (ESI) for RSC Advances.This journal is © The Royal Society of Chemistry 2016
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S2
14 13 12 11 10 9 8 7 6 5 4 3 2 1 0 ppm
0.0002
0.0751
0.0872
1.2525
2.5805
2.5847
2.5890
3.7663
3.8395
3.8614
3.8776
3.9869
4.0182
6.6386
6.6540
7.0844
7.4718
7.5161
7.7984
7.7998
7.8105
7.8262
7.8447
7.8603
13.1766
13.2106
3.73
3.74
1.03
1.04
1.14
1.41
1.00
Current Data Parameters
NAME Mar13-2013
EXPNO 340
PROCNO 1
F2 - Acquisition Parameters
Date_ 20130313
Time 17.08
INSTRUM spect
PROBHD 5 mm PABBO BB-
PULPROG zg30
TD 65536
SOLVENT DMSO
NS 8
DS 2
SWH 12019.230 Hz
FIDRES 0.183399 Hz
AQ 2.7263477 sec
RG 456
DW 41.600 usec
DE 6.00 usec
TE 294.5 K
D1 1.00000000 sec
TD0 1
======== CHANNEL f1 ========
NUC1 1H
P1 10.90 usec
PL1 -3.00 dB
SFO1 400.1324710 MHz
F2 - Processing parameters
SI 32768
SF 400.1299705 MHz
WDW EM
SSB 0
LB 0.30 Hz
GB 0
PC 1.00
DS-24BRUKER
AVANCE II 400 NMR
Spectrometer
SAIFPanjab University
Chandigarh
1H NMR
9a
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S3
200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm
38.95
39.17
39.37
39.58
39.79
40.00
40.21
55.65
56.00
77.50
77.82
78.15
98.04
108.37
112.95
136.15
136.81
144.51
153.67
168.17
Current Data Parameters
NAME Mar13-2013
EXPNO 341
PROCNO 1
F2 - Acquisition Parameters
Date_ 20130313
Time 18.57
INSTRUM spect
PROBHD 5 mm PABBO BB-
PULPROG zgpg30
TD 65536
SOLVENT DMSO
NS 100
DS 4
SWH 29761.904 Hz
FIDRES 0.454131 Hz
AQ 1.1010548 sec
RG 1030
DW 16.800 usec
DE 6.00 usec
TE 294.5 K
D1 2.00000000 sec
d11 0.03000000 sec
DELTA 1.89999998 sec
TD0 1
======== CHANNEL f1 ========
NUC1 13C
P1 9.60 usec
PL1 -2.00 dB
SFO1 100.6228298 MHz
======== CHANNEL f2 ========
CPDPRG2 waltz16
NUC2 1H
PCPD2 80.00 usec
PL2 -3.00 dB
PL12 14.31 dB
PL13 18.00 dB
SFO2 400.1316005 MHz
F2 - Processing parameters
SI 32768
SF 100.6128193 MHz
WDW EM
SSB 0
LB 1.00 Hz
GB 0
PC 1.40
DS-24 BRUKER
AVANCE II 400 NMR
Spectrometer
SAIF
Panjab University
Chandigarh
3d
13C NMR
9a
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S4
14 13 12 11 10 9 8 7 6 5 4 3 2 1 0 ppm
0.0006
2.5530
2.5573
2.5616
4.4395
4.4539
4.6974
4.7344
4.7796
4.8290
4.8371
4.8544
4.8703
4.9033
4.9465
6.6807
6.6964
7.1197
7.1372
7.1597
7.1633
7.1798
7.1959
7.1999
7.4046
7.4320
7.5354
7.5556
7.5892
7.5926
7.6103
7.6137
7.6322
7.6543
7.8781
7.8940
7.9119
7.9278
7.9969
8.0002
8.0165
8.0200
8.0411
8.0443
8.0614
8.0634
8.0701
8.6442
8.6719
8.6777
8.7054
13.0748
13.1085
1.39
1.38
0.22
2.43
1.15
1.25
0.14
1.00
Current Data Parameters
NAME Mar13-2013
EXPNO 290
PROCNO 1
F2 - Acquisition Parameters
Date_ 20130313
Time 15.02
INSTRUM spect
PROBHD 5 mm PABBO BB-
PULPROG zg30
TD 65536
SOLVENT DMSO
NS 8
DS 2
SWH 12019.230 Hz
FIDRES 0.183399 Hz
AQ 2.7263477 sec
RG 575
DW 41.600 usec
DE 6.00 usec
TE 295.0 K
D1 1.00000000 sec
TD0 1
======== CHANNEL f1 ========
NUC1 1H
P1 10.90 usec
PL1 -3.00 dB
SFO1 400.1324710 MHz
F2 - Processing parameters
SI 32768
SF 400.1299809 MHz
WDW EM
SSB 0
LB 0.30 Hz
GB 0
PC 1.00
DS-3BRUKER
AVANCE II 400 NMR
Spectrometer
SAIFPanjab University
Chandigarh
1H NMR
9b
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S5
200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm
38.91
39.12
39.33
39.54
39.75
39.96
40.16
78.13
78.46
78.79
113.48
114.72
116.57
123.04
131.72
134.11
136.79
140.88
168.43
Current Data Parameters
NAME Mar13-2013
EXPNO 291
PROCNO 1
F2 - Acquisition Parameters
Date_ 20130313
Time 18.26
INSTRUM spect
PROBHD 5 mm PABBO BB-
PULPROG zgpg30
TD 65536
SOLVENT DMSO
NS 60
DS 4
SWH 29761.904 Hz
FIDRES 0.454131 Hz
AQ 1.1010548 sec
RG 1030
DW 16.800 usec
DE 6.00 usec
TE 294.7 K
D1 2.00000000 sec
d11 0.03000000 sec
DELTA 1.89999998 sec
TD0 1
======== CHANNEL f1 ========
NUC1 13C
P1 9.60 usec
PL1 -2.00 dB
SFO1 100.6228298 MHz
======== CHANNEL f2 ========
CPDPRG2 waltz16
NUC2 1H
PCPD2 80.00 usec
PL2 -3.00 dB
PL12 14.31 dB
PL13 18.00 dB
SFO2 400.1316005 MHz
F2 - Processing parameters
SI 32768
SF 100.6128193 MHz
WDW EM
SSB 0
LB 1.00 Hz
GB 0
PC 1.40
DS-3 BRUKER
AVANCE II 400 NMR
Spectrometer
SAIF
Panjab University
Chandigarh
13C NMR
9b
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S6
10a
1H NMR
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S7
14 13 12 11 10 9 8 7 6 5 4 3 2 1 0 ppm
0.0000
1.9275
2.1153
2.1202
2.1601
2.5549
5.2574
7.3020
7.3201
7.3393
7.5560
7.5591
7.5766
7.5940
7.5969
7.6891
7.7094
8.0428
8.3157
8.3357
9.1074
6.24
1.20
1.11
1.07
1.02
1.00
Current Data Parameters
NAME Mar13-2013
EXPNO 300
PROCNO 1
F2 - Acquisition Parameters
Date_ 20130313
Time 15.07
INSTRUM spect
PROBHD 5 mm PABBO BB-
PULPROG zg30
TD 65536
SOLVENT DMSO
NS 8
DS 2
SWH 12019.230 Hz
FIDRES 0.183399 Hz
AQ 2.7263477 sec
RG 456
DW 41.600 usec
DE 6.00 usec
TE 294.9 K
D1 1.00000000 sec
TD0 1
======== CHANNEL f1 ========
NUC1 1H
P1 10.90 usec
PL1 -3.00 dB
SFO1 400.1324710 MHz
F2 - Processing parameters
SI 32768
SF 400.1299819 MHz
WDW EM
SSB 0
LB 0.30 Hz
GB 0
PC 1.00
DS-4BRUKER
AVANCE II 400 NMR
Spectrometer
SAIFPanjab University
Chandigarh
10b
1H NMR
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S8
200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm
21.64
38.87
39.07
39.28
39.49
39.70
39.91
40.12
78.07
78.40
78.73
123.81
125.38
125.95
129.22
129.32
130.82
147.04
148.19
168.89
173.29
Current Data Parameters
NAME Mar13-2013
EXPNO 301
PROCNO 1
F2 - Acquisition Parameters
Date_ 20130313
Time 18.33
INSTRUM spect
PROBHD 5 mm PABBO BB-
PULPROG zgpg30
TD 65536
SOLVENT DMSO
NS 72
DS 4
SWH 29761.904 Hz
FIDRES 0.454131 Hz
AQ 1.1010548 sec
RG 2050
DW 16.800 usec
DE 6.00 usec
TE 294.9 K
D1 2.00000000 sec
d11 0.03000000 sec
DELTA 1.89999998 sec
TD0 1
======== CHANNEL f1 ========
NUC1 13C
P1 9.60 usec
PL1 -2.00 dB
SFO1 100.6228298 MHz
======== CHANNEL f2 ========
CPDPRG2 waltz16
NUC2 1H
PCPD2 80.00 usec
PL2 -3.00 dB
PL12 14.31 dB
PL13 18.00 dB
SFO2 400.1316005 MHz
F2 - Processing parameters
SI 32768
SF 100.6128193 MHz
WDW EM
SSB 0
LB 1.00 Hz
GB 0
PC 1.40
DS-4 BRUKER
AVANCE II 400 NMR
Spectrometer
SAIF
Panjab University
Chandigarh
13C NMR
10b
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S9
12 11 10 9 8 7 6 5 4 3 2 1 0 ppm
0.0003
1.2514
2.1724
2.1801
2.5751
3.8335
3.8427
3.8940
3.9042
3.9616
5.0568
7.4766
7.4859
8.3867
8.3975
11.3693
3.00
7.67
1.07
0.87
0.68
Current Data Parameters
NAME Oct22-2014
EXPNO 210
PROCNO 1
F2 - Acquisition Parameters
Date_ 20141022
Time 22.15
INSTRUM spect
PROBHD 5 mm PABBO BB-
PULPROG zg30
TD 65536
SOLVENT DMSO
NS 8
DS 2
SWH 12019.230 Hz
FIDRES 0.183399 Hz
AQ 2.7263477 sec
RG 287
DW 41.600 usec
DE 6.00 usec
TE 298.2 K
D1 1.00000000 sec
TD0 1
======== CHANNEL f1 ========
NUC1 1H
P1 10.90 usec
PL1 -3.00 dB
SFO1 400.1324710 MHz
F2 - Processing parameters
SI 32768
SF 400.1299743 MHz
WDW EM
SSB 0
LB 0.30 Hz
GB 0
PC 1.00
MCV-1BRUKER
AVANCE II 400 NMR
Spectrometer
SAIFPanjab University
Chandigarh
11a
6 6
1H NMR
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S10
220 210 200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm
25.29
39.24
39.45
39.66
39.87
40.08
40.28
40.49
55.69
55.82
77.89
78.21
78.53
78.65
102.95
107.11
112.89
137.50
143.32
153.29
168.33
169.75
Current Data Parameters
NAME Oct22-2014
EXPNO 211
PROCNO 1
F2 - Acquisition Parameters
Date_ 20141022
Time 23.12
INSTRUM spect
PROBHD 5 mm PABBO BB-
PULPROG zgpg30
TD 65536
SOLVENT DMSO
NS 1024
DS 4
SWH 29761.904 Hz
FIDRES 0.454131 Hz
AQ 1.1010548 sec
RG 1030
DW 16.800 usec
DE 6.00 usec
TE 298.7 K
D1 2.00000000 sec
d11 0.03000000 sec
DELTA 1.89999998 sec
TD0 1
======== CHANNEL f1 ========
NUC1 13C
P1 9.60 usec
PL1 -2.00 dB
SFO1 100.6228298 MHz
======== CHANNEL f2 ========
CPDPRG2 waltz16
NUC2 1H
PCPD2 80.00 usec
PL2 -3.00 dB
PL12 14.31 dB
PL13 18.00 dB
SFO2 400.1316005 MHz
F2 - Processing parameters
SI 32768
SF 100.6127906 MHz
WDW EM
SSB 0
LB 1.00 Hz
GB 0
PC 1.40
MCV-1 BRUKER
AVANCE II 400 NMR
Spectrometer
SAIF
Panjab University
Chandigarh
13C NMR
11a
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S11
7.27.47.67.88.08.28.48.68.89.09.29.49.6 ppm
7.4673
7.4757
7.5056
7.5547
7.5959
7.6063
7.8064
7.8915
7.9354
7.9564
8.0398
8.0761
8.1699
8.1865
8.4679
8.5284
9.1491
9.1719
9.2870
1.03
2.02
1.02
1.00
Current Data Parameters
NAME Mar13-2013
EXPNO 310
PROCNO 1
F2 - Acquisition Parameters
Date_ 20130313
Time 15.12
INSTRUM spect
PROBHD 5 mm PABBO BB-
PULPROG zg30
TD 65536
SOLVENT DMSO
NS 8
DS 2
SWH 12019.230 Hz
FIDRES 0.183399 Hz
AQ 2.7263477 sec
RG 724
DW 41.600 usec
DE 6.00 usec
TE 295.0 K
D1 1.00000000 sec
TD0 1
======== CHANNEL f1 ========
NUC1 1H
P1 10.90 usec
PL1 -3.00 dB
SFO1 400.1324710 MHz
F2 - Processing parameters
SI 32768
SF 400.1299700 MHz
WDW EM
SSB 0
LB 0.30 Hz
GB 0
PC 1.00
DS-5BRUKER
AVANCE II 400 NMR
Spectrometer
SAIFPanjab University
Chandigarh
11b
1H NMR
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S12
1a
1H NMR
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S13
1H NMR
1a
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S14
1H NMR
1a
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S15
WATERS, Q-TOF MICROMASS (ESI-MS) SAIF/CIL,PANJAB UNIVERSITY,CHANDIGARH
m/z75 100 125 150 175 200 225 250 275 300 325 350 375 400 425 450 475 500 525 550 575 600 625 650 675 700 725 750 775 800
%
0
100
RAJ KUMAR MCV-4 6 (0.175) AM (Top,10, Ar,5000.0,556.28,0.70,LS 10); Sm (Mn, 2x3.00); Sb (1,40.00 ); Cm (5:8-13:23) 1: TOF MS ES+ 1.67e4271.0905
16685
263.077513594
118.389912616
67.65827746
77.81651321
99.1247485
251.02542907
250.03752037
119.87591771
187.84001050148.6196
569248.0982
770
394.05855493
273.02784205
283.3083865 382.0411
558316.0233;462
628.32152322
396.06171532
397.0604339
434.0931236 521.8998
110563.0738
39610.2061
21
629.3229876
630.3372;158686.3726
9790.0239
6
769.08956
HRMS
1a
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S16
12 11 10 9 8 7 6 5 4 3 2 1 ppm
0.0000
3.4173
3.9627
6.7432
6.9251
6.9335
6.9419
6.9470
6.9551
6.9637
7.0681
7.0894
7.1109
7.1453
7.1519
7.1608
7.1675
7.2001
7.2999
9.2749
10.1101
3.34
3.33
1.10
1.10
1.09
1.05
1.11
1.00
1.09
Current Data Parameters
NAME Jan22-2014
EXPNO 390
PROCNO 1
F2 - Acquisition Parameters
Date_ 20140122
Time 18.44
INSTRUM spect
PROBHD 5 mm PABBO BB-
PULPROG zg30
TD 65536
SOLVENT CDCl3
NS 8
DS 2
SWH 12019.230 Hz
FIDRES 0.183399 Hz
AQ 2.7263477 sec
RG 287
DW 41.600 usec
DE 6.00 usec
TE 295.2 K
D1 1.00000000 sec
TD0 1
======== CHANNEL f1 ========
NUC1 1H
P1 10.90 usec
PL1 -3.00 dB
SFO1 400.1324710 MHz
F2 - Processing parameters
SI 32768
SF 400.1300337 MHz
WDW EM
SSB 0
LB 0.30 Hz
GB 0
PC 1.00
MCV-4BRUKER
AVANCE II 400 NMR
Spectrometer
SAIFPanjab University
Chandigarh
1b
1H NMR
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S17
6.46.56.66.76.86.97.07.17.27.37.47.5 ppm
6.7432
6.9251
6.9335
6.9419
6.9470
6.9551
6.9637
7.0681
7.0894
7.1109
7.1453
7.1519
7.1608
7.1675
7.2001
7.2999
1.10
1.10
1.09
1.05
1.11
Current Data Parameters
NAME Jan22-2014
EXPNO 390
PROCNO 1
F2 - Acquisition Parameters
Date_ 20140122
Time 18.44
INSTRUM spect
PROBHD 5 mm PABBO BB-
PULPROG zg30
TD 65536
SOLVENT CDCl3
NS 8
DS 2
SWH 12019.230 Hz
FIDRES 0.183399 Hz
AQ 2.7263477 sec
RG 287
DW 41.600 usec
DE 6.00 usec
TE 295.2 K
D1 1.00000000 sec
TD0 1
======== CHANNEL f1 ========
NUC1 1H
P1 10.90 usec
PL1 -3.00 dB
SFO1 400.1324710 MHz
F2 - Processing parameters
SI 32768
SF 400.1300337 MHz
WDW EM
SSB 0
LB 0.30 Hz
GB 0
PC 1.00
MCV-4BRUKER
AVANCE II 400 NMR
Spectrometer
SAIFPanjab University
Chandigarh
1H NMR
1b
![Page 18: Dual inhibitors of epidermal growth factor receptor and ...S1 Dual inhibitors of epidermal growth factor receptor and topoisomerase IIα derived from quinoline scaffold Monika Chauhan,a](https://reader034.vdocuments.site/reader034/viewer/2022051902/5ff2a5f8ddeec7176661cd27/html5/thumbnails/18.jpg)
S18
3.13.23.33.43.53.63.73.83.94.04.14.24.3 ppm
3.4173
3.9627
3.34
3.33
Current Data Parameters
NAME Jan22-2014
EXPNO 390
PROCNO 1
F2 - Acquisition Parameters
Date_ 20140122
Time 18.44
INSTRUM spect
PROBHD 5 mm PABBO BB-
PULPROG zg30
TD 65536
SOLVENT CDCl3
NS 8
DS 2
SWH 12019.230 Hz
FIDRES 0.183399 Hz
AQ 2.7263477 sec
RG 287
DW 41.600 usec
DE 6.00 usec
TE 295.2 K
D1 1.00000000 sec
TD0 1
======== CHANNEL f1 ========
NUC1 1H
P1 10.90 usec
PL1 -3.00 dB
SFO1 400.1324710 MHz
F2 - Processing parameters
SI 32768
SF 400.1300337 MHz
WDW EM
SSB 0
LB 0.30 Hz
GB 0
PC 1.00
MCV-4BRUKER
AVANCE II 400 NMR
Spectrometer
SAIFPanjab University
Chandigarh
1H NMR
1b
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S19
220 210 200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm
55.54
56.41
76.73
77.05
77.25
77.37
105.50
109.37
112.77
117.20
117.42
121.99
122.18
122.99
123.05
125.42
129.17
137.96
138.00
144.12
145.04
148.24
148.69
154.45
154.53
156.93
Current Data Parameters
NAME Jan22-2014
EXPNO 391
PROCNO 1
F2 - Acquisition Parameters
Date_ 20140122
Time 18.52
INSTRUM spect
PROBHD 5 mm PABBO BB-
PULPROG zgpg30
TD 65536
SOLVENT CDCl3
NS 864
DS 4
SWH 29761.904 Hz
FIDRES 0.454131 Hz
AQ 1.1010548 sec
RG 1030
DW 16.800 usec
DE 6.00 usec
TE 295.7 K
D1 2.00000000 sec
d11 0.03000000 sec
DELTA 1.89999998 sec
TD0 1
======== CHANNEL f1 ========
NUC1 13C
P1 9.60 usec
PL1 -2.00 dB
SFO1 100.6228298 MHz
======== CHANNEL f2 ========
CPDPRG2 waltz16
NUC2 1H
PCPD2 80.00 usec
PL2 -3.00 dB
PL12 14.31 dB
PL13 18.00 dB
SFO2 400.1316005 MHz
F2 - Processing parameters
SI 32768
SF 100.6127690 MHz
WDW EM
SSB 0
LB 1.00 Hz
GB 0
PC 1.40
MCV-4 BRUKER
AVANCE II 400 NMR
Spectrometer
SAIF
Panjab University
Chandigarh
13C NMR
1b
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S20
105110115120125130135140145150155160 ppm
105.50
109.37
112.77
117.20
117.42
121.99
122.18
122.99
123.05
125.42
129.17
137.96
138.00
144.12
145.04
148.24
148.69
154.45
154.53
156.93
Current Data Parameters
NAME Jan22-2014
EXPNO 391
PROCNO 1
F2 - Acquisition Parameters
Date_ 20140122
Time 18.52
INSTRUM spect
PROBHD 5 mm PABBO BB-
PULPROG zgpg30
TD 65536
SOLVENT CDCl3
NS 864
DS 4
SWH 29761.904 Hz
FIDRES 0.454131 Hz
AQ 1.1010548 sec
RG 1030
DW 16.800 usec
DE 6.00 usec
TE 295.7 K
D1 2.00000000 sec
d11 0.03000000 sec
DELTA 1.89999998 sec
TD0 1
======== CHANNEL f1 ========
NUC1 13C
P1 9.60 usec
PL1 -2.00 dB
SFO1 100.6228298 MHz
======== CHANNEL f2 ========
CPDPRG2 waltz16
NUC2 1H
PCPD2 80.00 usec
PL2 -3.00 dB
PL12 14.31 dB
PL13 18.00 dB
SFO2 400.1316005 MHz
F2 - Processing parameters
SI 32768
SF 100.6127690 MHz
WDW EM
SSB 0
LB 1.00 Hz
GB 0
PC 1.40
MCV-4 BRUKER
AVANCE II 400 NMR
Spectrometer
SAIF
Panjab University
Chandigarh
13C NMR
1b
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S21
WATERS, Q-TOF MICROMASS (ESI-MS) SAIF/CIL,PANJAB UNIVERSITY,CHANDIGARH
m/z75 100 125 150 175 200 225 250 275 300 325 350 375 400 425 450 475 500 525 550 575 600 625 650 675 700 725 750 775 800
%
0
100
RAJ KUMAR MCV-12- 7 (0.195) AM (Top,10, Ar,5000.0,556.28,0.70,LS 10); Sm (Mn, 2x3.00); Sb (1,40.00 ); Cm (6:8-12:20) 1: TOF MS ES+ 1.88e4378.0435
18758
283.30595637
281.03874259
148.61672840
118.39241202
83.95291029
263.09091414
220.9915608
185.8647463
316.02123639
355.07623543
318.02442033
336.10421028
628.310214858
384.145611944
610.18273705
385.15782418
536.15691210
503.1051911444.0084
771386.1523
557485.3420
52
537.1721518
629.33595287
684.2072620
630.3381611
758.2203226
737.68748
776.25132
HRMS
1b
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S22
1c
1H NMR
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S23
MASS
1c
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S24
1d
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S25
200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 ppm
29.71
76.74
77.06
77.38
118.88
123.50
125.59
126.47
127.52
128.51
129.86
130.34
132.64
140.95
146.71
146.75
150.42
Current Data Parameters
NAME Mar13-2013
EXPNO 331
PROCNO 1
F2 - Acquisition Parameters
Date_ 20130313
Time 18.43
INSTRUM spect
PROBHD 5 mm PABBO BB-
PULPROG zgpg30
TD 65536
SOLVENT CDCl3
NS 124
DS 4
SWH 29761.904 Hz
FIDRES 0.454131 Hz
AQ 1.1010548 sec
RG 1030
DW 16.800 usec
DE 6.00 usec
TE 294.7 K
D1 2.00000000 sec
d11 0.03000000 sec
DELTA 1.89999998 sec
TD0 1
======== CHANNEL f1 ========
NUC1 13C
P1 9.60 usec
PL1 -2.00 dB
SFO1 100.6228298 MHz
======== CHANNEL f2 ========
CPDPRG2 waltz16
NUC2 1H
PCPD2 80.00 usec
PL2 -3.00 dB
PL12 14.31 dB
PL13 18.00 dB
SFO2 400.1316005 MHz
F2 - Processing parameters
SI 32768
SF 100.6127690 MHz
WDW EM
SSB 0
LB 1.00 Hz
GB 0
PC 1.40
DS-6b BRUKER
AVANCE II 400 NMR
Spectrometer
SAIF
Panjab University
Chandigarh
1d
1H NMR
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S26
12 11 10 9 8 7 6 5 4 3 2 1 0 ppm
0.0005
0.8106
1.1861
1.2144
2.0522
2.1628
3.4264
3.8213
3.8473
3.9039
3.9691
7.1931
7.4273
8.4015
10.8953
1.30
4.84
2.36
4.51
5.93
5.60
2.81
1.39
1.06
1.00
Current Data Parameters
NAME Oct13-2014
EXPNO 200
PROCNO 1
F2 - Acquisition Parameters
Date_ 20141014
Time 0.58
INSTRUM spect
PROBHD 5 mm PABBO BB-
PULPROG zg30
TD 65536
SOLVENT CDCl3
NS 8
DS 2
SWH 12019.230 Hz
FIDRES 0.183399 Hz
AQ 2.7263477 sec
RG 575
DW 41.600 usec
DE 6.00 usec
TE 297.9 K
D1 1.00000000 sec
TD0 1
======== CHANNEL f1 ========
NUC1 1H
P1 10.90 usec
PL1 -3.00 dB
SFO1 400.1324710 MHz
F2 - Processing parameters
SI 32768
SF 400.1300363 MHz
WDW EM
SSB 0
LB 0.30 Hz
GB 0
PC 1.00
MCV-1BRUKER
AVANCE II 400 NMR
Spectrometer
SAIFPanjab University
Chandigarh
2a
1H NMR
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S27
14 13 12 11 10 9 8 7 6 5 4 3 2 1 0 ppm
0.0000
1.2451
2.1219
2.5563
2.5598
3.3478
6.8243
7.1977
7.2265
7.2334
7.3863
7.4052
7.4170
7.4247
7.4377
7.4851
7.5058
7.6908
7.7092
7.7278
7.7293
7.9247
7.9448
7.9649
7.9851
8.0547
8.1229
8.1437
8.3063
8.3266
12.9630
1.21
1.04
1.00
1.11
0.94
Current Data Parameters
NAME Aug28-2015
EXPNO 440
PROCNO 1
F2 - Acquisition Parameters
Date_ 20150828
Time 15.48
INSTRUM spect
PROBHD 5 mm PABBO BB-
PULPROG zg30
TD 65536
SOLVENT DMSO
NS 8
DS 2
SWH 12019.230 Hz
FIDRES 0.183399 Hz
AQ 2.7263477 sec
RG 575
DW 41.600 usec
DE 6.00 usec
TE 297.3 K
D1 1.00000000 sec
TD0 1
======== CHANNEL f1 ========
NUC1 1H
P1 10.90 usec
PL1 -3.00 dB
SFO1 400.1324710 MHz
F2 - Processing parameters
SI 32768
SF 400.1299816 MHz
WDW EM
SSB 0
LB 0.30 Hz
GB 0
PC 1.00
NAG-1BRUKER
AVANCE II 400 NMR
Spectrometer
SAIFPanjab University
Chandigarh
2l
1H NMR
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S28
12 11 10 9 8 7 6 5 4 3 2 1 0 ppm
1.8941
2.4915
2.5099
2.5138
3.2043
3.3708
3.9087
3.9281
3.9538
6.9705
6.9920
7.0506
7.0722
7.9284
7.9670
7.9800
8.0185
8.0565
8.1824
8.1872
8.2038
8.2087
8.2622
8.2672
8.4199
8.4417
8.5360
8.5406
8.5519
8.5574
8.7935
8.7990
1.10
2.90
0.28
1.08
1.82
0.86
1.01
1.01
2.00
1.14
Current Data Parameters
NAME Oct13-2014
EXPNO 210
PROCNO 1
F2 - Acquisition Parameters
Date_ 20141014
Time 1.32
INSTRUM spect
PROBHD 5 mm PABBO BB-
PULPROG zg30
TD 65536
SOLVENT DMSO
NS 8
DS 2
SWH 12019.230 Hz
FIDRES 0.183399 Hz
AQ 2.7263477 sec
RG 406
DW 41.600 usec
DE 6.00 usec
TE 298.0 K
D1 1.00000000 sec
TD0 1
======== CHANNEL f1 ========
NUC1 1H
P1 10.90 usec
PL1 -3.00 dB
SFO1 400.1324710 MHz
F2 - Processing parameters
SI 32768
SF 400.1300000 MHz
WDW EM
SSB 0
LB 0.30 Hz
GB 0
PC 1.00
PAR-1BRUKER
AVANCE II 400 NMR
Spectrometer
SAIFPanjab University
Chandigarh
16
1H NMR
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S29
17
1H NMR
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S30
7.17.27.37.47.57.67.77.87.98.0 ppm
7.1803
7.1885
7.1989
7.2034
7.2058
7.2141
7.2211
7.2246
7.2303
7.2434
7.2489
7.3434
7.3466
7.3568
7.3607
7.3645
7.3679
7.3736
7.3751
7.3805
7.3851
7.3913
7.5605
7.5637
7.5778
7.5812
7.5848
7.5989
7.6021
7.8476
7.8489
7.8675
7.8868
7.8883
2.82
3.12
1.16
1.97
Current Data Parameters
NAME Aug04-2014
EXPNO 40
PROCNO 1
F2 - Acquisition Parameters
Date_ 20140804
Time 11.03
INSTRUM spect
PROBHD 5 mm PABBO BB-
PULPROG zg30
TD 65536
SOLVENT CDCl3
NS 8
DS 2
SWH 12019.230 Hz
FIDRES 0.183399 Hz
AQ 2.7263477 sec
RG 724
DW 41.600 usec
DE 6.00 usec
TE 296.4 K
D1 1.00000000 sec
TD0 1
======== CHANNEL f1 ========
NUC1 1H
P1 10.90 usec
PL1 -3.00 dB
SFO1 400.1324710 MHz
F2 - Processing parameters
SI 32768
SF 400.1300382 MHz
WDW EM
SSB 0
LB 0.30 Hz
GB 0
PC 1.00
ARP-15BRUKER
AVANCE II 400 NMR
Spectrometer
SAIFPanjab University
Chandigarh
1H NMR
17
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S31
12 11 10 9 8 7 6 5 4 3 2 1 0 ppm
-0.0079
0.0002
0.0081
0.7953
0.8108
0.8220
0.8524
1.2553
1.3105
1.4003
1.4185
1.4364
1.5863
1.6871
3.1012
3.1132
3.1192
3.1312
6.6770
6.6985
6.7928
6.8146
6.8709
6.8928
7.0144
7.0203
7.0358
7.0418
7.0595
7.0628
7.0761
7.0813
7.0978
7.1017
7.1033
7.1297
7.2410
7.2470
7.2614
7.2984
7.3044
7.3207
7.3268
7.4069
7.4431
7.4453
7.4653
7.4714
7.5165
7.5232
7.5293
7.6041
7.6075
7.6212
7.6250
7.6285
7.6423
7.6456
7.6934
7.7122
7.7145
8.7130
8.7354
8.9408
10.1259
10.2866
2.87
2.32
0.76
0.58
1.07
0.69
2.35
2.99
1.13
1.56
1.29
1.35
1.11
0.97
0.95
1.00
Current Data Parameters
NAME Aug28-2015
EXPNO 450
PROCNO 1
F2 - Acquisition Parameters
Date_ 20150828
Time 15.54
INSTRUM spect
PROBHD 5 mm PABBO BB-
PULPROG zg30
TD 65536
SOLVENT CDCl3
NS 8
DS 2
SWH 12019.230 Hz
FIDRES 0.183399 Hz
AQ 2.7263477 sec
RG 575
DW 41.600 usec
DE 6.00 usec
TE 297.3 K
D1 1.00000000 sec
TD0 1
======== CHANNEL f1 ========
NUC1 1H
P1 10.90 usec
PL1 -3.00 dB
SFO1 400.1324710 MHz
F2 - Processing parameters
SI 32768
SF 400.1300091 MHz
WDW EM
SSB 0
LB 0.30 Hz
GB 0
PC 1.00
NAG-2BRUKER
AVANCE II 400 NMR
Spectrometer
SAIFPanjab University
Chandigarh
3l
1H NMR
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S32
1H NMR
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S33
6.56.66.76.86.97.07.17.27.37.47.57.67.77.87.98.08.18.28.38.48.5 ppm
6.9965
7.1804
7.1869
7.1921
7.2036
7.2088
7.2151
7.2604
7.5180
7.5258
7.5319
7.5400
7.6947
7.7032
7.7091
7.7173
7.9869
7.9918
8.0036
8.0087
2.57
1.52
1.07
2.00
Current Data Parameters
NAME May27-2015
EXPNO 200
PROCNO 1
F2 - Acquisition Parameters
Date_ 20150527
Time 15.45
INSTRUM spect
PROBHD 5 mm PABBO BB-
PULPROG zg30
TD 65536
SOLVENT CDCl3
NS 8
DS 2
SWH 12019.230 Hz
FIDRES 0.183399 Hz
AQ 2.7263477 sec
RG 912
DW 41.600 usec
DE 6.00 usec
TE 297.9 K
D1 1.00000000 sec
TD0 1
======== CHANNEL f1 ========
NUC1 1H
P1 10.90 usec
PL1 -3.00 dB
SFO1 400.1324710 MHz
F2 - Processing parameters
SI 32768
SF 400.1300094 MHz
WDW EM
SSB 0
LB 0.30 Hz
GB 0
PC 1.00
AK-9BBRUKER
AVANCE II 400 NMR
Spectrometer
SAIFPanjab University
Chandigarh
1H NMR
4b
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S34
3.94.04.14.24.34.44.54.64.74.84.95.05.15.25.35.45.55.65.75.8 ppm
4.0553
4.0702
4.0835
4.0961
4.1131
4.1311
4.1508
4.1671
4.1956
4.2030
4.2187
4.2329
5.2993
5.3450
2.33
1.61
0.86
3.68
0.84
Current Data Parameters
NAME May27-2015
EXPNO 200
PROCNO 1
F2 - Acquisition Parameters
Date_ 20150527
Time 15.45
INSTRUM spect
PROBHD 5 mm PABBO BB-
PULPROG zg30
TD 65536
SOLVENT CDCl3
NS 8
DS 2
SWH 12019.230 Hz
FIDRES 0.183399 Hz
AQ 2.7263477 sec
RG 912
DW 41.600 usec
DE 6.00 usec
TE 297.9 K
D1 1.00000000 sec
TD0 1
======== CHANNEL f1 ========
NUC1 1H
P1 10.90 usec
PL1 -3.00 dB
SFO1 400.1324710 MHz
F2 - Processing parameters
SI 32768
SF 400.1300094 MHz
WDW EM
SSB 0
LB 0.30 Hz
GB 0
PC 1.00
AK-9BBRUKER
AVANCE II 400 NMR
Spectrometer
SAIFPanjab University
Chandigarh
1H NMR
4b
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S35
WATERS, Q-TOF MICROMASS (ESI-MS) SAIF/CIL,PANJAB UNIVERSITY,CHANDIGARH
m/z50 75 100 125 150 175 200 225 250 275 300 325 350 375 400 425 450 475 500 525 550 575 600 625 650 675 700 725 750 775
%
0
100
RAJ KUMAR MAK-9 6 (0.177) AM (Top,10, Ar,5000.0,556.28,0.70,LS 10); Sm (Mn, 2x3.00); Sb (1,40.00 ); Cm (5:9-13:24) 1: TOF MS ES+ 4.58e4306.2607
45843
278.218928103
261.07836577
250.17382526
148.61811359
123.46411128
214.0079690
334.292940659
362.331923914
390.361510167
418.39813719
446.4295880
486.1963381
514.2251253 685.4346
144584.3060
99
610.199990 727.4645
30
746.56469
HRMS
4b
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S36
12 11 10 9 8 7 6 5 4 3 2 1 0 ppm
0.0000
0.8116
0.8366
0.8442
0.8530
0.8620
0.8701
0.8798
0.8960
1.2309
1.2547
1.2844
1.3342
1.4019
1.4219
1.6869
2.0442
4.0436
4.2683
7.2567
7.3118
7.3797
7.4260
7.4301
7.4343
7.4429
7.4482
7.4554
7.4621
7.4666
7.4761
7.4804
7.4932
7.4976
7.5166
7.5299
7.5335
7.5411
7.5489
7.5521
7.5536
7.5657
7.5747
7.5803
7.5915
7.5954
7.5985
7.6326
7.6380
7.6496
7.6532
7.6563
7.8507
7.8547
7.8719
7.8759
7.8957
7.9100
7.9193
7.9340
7.9924
8.0135
8.0362
8.0548
8.0589
5.61
13.18
1.94
3.02
2.19
1.60
0.78
1.01
3.41
2.77
1.08
3.72
1.02
1.02
1.00
Current Data Parameters
NAME Mar16-2015
EXPNO 130
PROCNO 1
F2 - Acquisition Parameters
Date_ 20150316
Time 14.10
INSTRUM spect
PROBHD 5 mm PABBO BB-
PULPROG zg30
TD 65536
SOLVENT CDCl3
NS 8
DS 2
SWH 12019.230 Hz
FIDRES 0.183399 Hz
AQ 2.7263477 sec
RG 287
DW 41.600 usec
DE 6.00 usec
TE 294.1 K
D1 1.00000000 sec
TD0 1
======== CHANNEL f1 ========
NUC1 1H
P1 10.90 usec
PL1 -3.00 dB
SFO1 400.1324710 MHz
F2 - Processing parameters
SI 32768
SF 400.1300111 MHz
WDW EM
SSB 0
LB 0.30 Hz
GB 0
PC 1.00
RB-7BRUKER
AVANCE II 400 NMR
Spectrometer
SAIFPanjab University
Chandigarh
5a
1H NMR
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S37
230 220 210 200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm
14.16
29.65
29.73
76.73
77.05
77.37
116.35
116.67
125.43
125.85
126.37
126.41
126.47
126.71
126.83
127.22
127.80
128.11
128.17
128.46
128.82
129.04
129.13
129.24
133.38
133.40
135.73
137.13
138.34
142.88
150.52
Current Data Parameters
NAME Mar23-2015
EXPNO 431
PROCNO 1
F2 - Acquisition Parameters
Date_ 20150324
Time 3.02
INSTRUM spect
PROBHD 5 mm PABBO BB-
PULPROG zgpg30
TD 65536
SOLVENT CDCl3
NS 1024
DS 4
SWH 29761.904 Hz
FIDRES 0.454131 Hz
AQ 1.1010548 sec
RG 575
DW 16.800 usec
DE 6.00 usec
TE 294.1 K
D1 2.00000000 sec
d11 0.03000000 sec
DELTA 1.89999998 sec
TD0 1
======== CHANNEL f1 ========
NUC1 13C
P1 9.60 usec
PL1 -2.00 dB
SFO1 100.6228298 MHz
======== CHANNEL f2 ========
CPDPRG2 waltz16
NUC2 1H
PCPD2 80.00 usec
PL2 -3.00 dB
PL12 14.31 dB
PL13 18.00 dB
SFO2 400.1316005 MHz
F2 - Processing parameters
SI 32768
SF 100.6127690 MHz
WDW EM
SSB 0
LB 1.00 Hz
GB 0
PC 1.40
RB-7 BRUKER
AVANCE II 400 NMR
Spectrometer
SAIF
Panjab University
Chandigarh
13C NMR
5a
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S38
WATERS, Q-TOF MICROMASS (ESI-MS) SAIF/CIL,PANJAB UNIVERSITY,CHANDIGARH
m/z75 100 125 150 175 200 225 250 275 300 325 350 375 400 425 450 475 500 525 550 575 600 625 650 675 700 725 750 775
%
0
100
RAJ KUMAR MAK-6 13 (0.389) AM (Top,10, Ar,5000.0,556.28,0.70,LS 10); Sm (Mn, 2x3.00); Sb (1,40.00 ) 1: TOF MS ES+ 1.23e4271.0839
12298
101.1678885
118.3905343
180.8007313 249.1144
93
475.31412917
272.10392786
453.33501004
359.2392290
273.1178230 342.2601
9435.3237
74
384.187315
476.3232698 701.4988
467
679.5175447
477.3545;75649.1594;11
610.161110
536.13734 703.5121;22
749.67901
HRMS
5a
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S39
11 10 9 8 7 6 5 4 3 2 1 0 ppm
0.0000
0.0729
0.8364
0.8444
0.8529
0.8621
0.8697
0.8800
0.8963
1.2409
1.2552
1.2763
1.2828
1.2868
1.2979
1.4097
1.4255
2.0457
2.6655
7.2621
7.3752
7.4479
7.4523
7.4572
7.4647
7.4715
7.4771
7.4821
7.6238
7.6299
7.6440
7.6476
7.8819
7.8856
7.8985
7.9029
7.9961
7.9974
8.0144
8.0198
8.1014
8.1056
8.1180
8.1223
3.07
1.02
2.01
1.05
1.99
1.01
2.00
Current Data Parameters
NAME Mar16-2015
EXPNO 140
PROCNO 1
F2 - Acquisition Parameters
Date_ 20150316
Time 14.15
INSTRUM spect
PROBHD 5 mm PABBO BB-
PULPROG zg30
TD 65536
SOLVENT CDCl3
NS 8
DS 2
SWH 12019.230 Hz
FIDRES 0.183399 Hz
AQ 2.7263477 sec
RG 228
DW 41.600 usec
DE 6.00 usec
TE 294.0 K
D1 1.00000000 sec
TD0 1
======== CHANNEL f1 ========
NUC1 1H
P1 10.90 usec
PL1 -3.00 dB
SFO1 400.1324710 MHz
F2 - Processing parameters
SI 32768
SF 400.1300089 MHz
WDW EM
SSB 0
LB 0.30 Hz
GB 0
PC 1.00
RB-8BRUKER
AVANCE II 400 NMR
Spectrometer
SAIFPanjab University
Chandigarh
1H NMR
5b
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S40
6.97.07.17.27.37.47.57.67.77.87.98.08.18.28.38.48.58.6 ppm
7.2621
7.3752
7.4479
7.4523
7.4572
7.4647
7.4715
7.4771
7.4821
7.6238
7.6299
7.6440
7.6476
7.8819
7.8856
7.8985
7.9029
7.9961
7.9974
8.0144
8.0198
8.1014
8.1056
8.1180
8.1223
1.02
2.01
1.05
1.99
1.01
2.00
Current Data Parameters
NAME Mar16-2015
EXPNO 140
PROCNO 1
F2 - Acquisition Parameters
Date_ 20150316
Time 14.15
INSTRUM spect
PROBHD 5 mm PABBO BB-
PULPROG zg30
TD 65536
SOLVENT CDCl3
NS 8
DS 2
SWH 12019.230 Hz
FIDRES 0.183399 Hz
AQ 2.7263477 sec
RG 228
DW 41.600 usec
DE 6.00 usec
TE 294.0 K
D1 1.00000000 sec
TD0 1
======== CHANNEL f1 ========
NUC1 1H
P1 10.90 usec
PL1 -3.00 dB
SFO1 400.1324710 MHz
F2 - Processing parameters
SI 32768
SF 400.1300089 MHz
WDW EM
SSB 0
LB 0.30 Hz
GB 0
PC 1.00
RB-8BRUKER
AVANCE II 400 NMR
Spectrometer
SAIFPanjab University
Chandigarh
1H NMR
5b
![Page 41: Dual inhibitors of epidermal growth factor receptor and ...S1 Dual inhibitors of epidermal growth factor receptor and topoisomerase IIα derived from quinoline scaffold Monika Chauhan,a](https://reader034.vdocuments.site/reader034/viewer/2022051902/5ff2a5f8ddeec7176661cd27/html5/thumbnails/41.jpg)
S41
WATERS, Q-TOF MICROMASS (ESI-MS) SAIF/CIL,PANJAB UNIVERSITY,CHANDIGARH
m/z262 263 264 265 266
%
0
100
RAJ KUMAR AK-7- 6 (0.176) AM (Top,10, Ar,5000.0,556.28,0.70,LS 10); Sm (Mn, 2x3.00); Sb (1,40.00 ); Cm (6:8-11:16) 1: TOF MS ES+ 3.13e4263.0510
31322
262.6085204
261.9454153
261.495962
262.1032151
262.9167180
263.810511885
263.628519
264.079810145
265.0946779264.8249
28264.4839
5
266.0796110
265.50751
HRMS
1H NMR
5b