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Organic & Biomolecular Chemistry
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Journal Name
ARTICLE
(s, 1H, SO2NHCONH), 10.62 (s, 1H, SO2NHCONH), 8.24 (s, 1H, Ar‐H), alkene), 5.82 (s, 1H, pyrimidine‐H), 5.75 (dt, J = 11.88, 7.19 Hz, 1H,
8.03 (d, J = 7.66 Hz, 1H, Ar‐H), 7.76 (d, J = 16.06 Hz, 1H, ArCH=CH, ArCH=CH), 3.98 (s, 6H, pyrimidine‐OCH3), 2.6D8O(sI:, 130H.1,0A3r9‐/CCH63O),B20.135755(pG,
trans alkene), 7.52 (d, J = 7.98 Hz, 1H, Ar‐H), 6.71 (d, J = 16.07 Hz, 1H, J = 7.40 Hz, 2H, =CHCH2CH3), 1.09 (t, J = 7.63 Hz, 3H, =CHCH2CH3). 13
C
ArCH=CH), 6.02 (s, 1H, pyrimidine‐H), 3.92 (s, 6H, pyrimidine‐OCH3), NMR (101 MHz, CDCl3) δ 171.43, 155.48, 148.70, 136.61, 136.41,
3.74 (s, 3H, COOCH3), 2.62 (s, 3H, Ar‐CH3). 13C NMR (101 MHz, DMSO‐ 135.08, 133.74, 132.23, 131.30, 128.61, 126.40, 85.20, 54.81, 21.91,
d6) δ 171.15, 166.31, 156.00, 148.46, 142.59, 138.96, 137.60, 133.26, 19.93, 14.33. HRMS for C18H22N4O5S: calcd 407.1384 [M+H], found
132.41, 132.36, 130.31, 119.20, 83.73, 54.62, 51.59, 19.49. HRMS for 407.1389.
C18H20N4O7S: calcd 437.1125 [M+H], found 437.1128.
(Z)‐5‐(but‐1‐en‐1‐yl)‐N‐((4,6‐dimethylpyrimidin‐2‐yl)carbamoyl)‐2‐
Methyl (E)‐3‐(3‐(N‐((4,6‐dimethylpyrimidin‐2‐ methylbenzenesulfonamide (9j). white solid, yield 81.6%, m.p. 140
yl)carbamoyl)sulfamoyl)‐4‐methylphenyl)acrylate (9e). white solid, – 141 °C. 1H NMR (400 MHz, DMSO‐d6) δ 13.43 (s, 1H, SO2NHCONH),
yield 65.8%, m.p. 178 – 179 °C. 1H NMR (400 MHz, DMSO‐d6) δ 13.46 10.63 (s, 1H, SO2NHCONH), 7.94 (s, 1H, Ar‐H), 7.50 (d, J = 7.62 Hz, 1H,
(s, 1H, SO2NHCONH), 10.61 (s, 1H, SO2NHCONH), 8.23 (s, 1H, Ar‐H), Ar‐H), 7.42 (d, J = 7.87 Hz, 1H, Ar‐H), 7.02 (s, 1H, pyrimidine‐H), 6.44
8.01 (d, J = 7.79 Hz, 1H, Ar‐H), 7.76 (d, J = 16.07 Hz, 1H, ArCH=CH, (d, J = 11.64 Hz, 1H, ArCH=CH, cis alkene), 5.75 (dt, J = 11.54, 7.36 Hz,
trans alkene), 7.50 (d, J = 7.95 Hz, 1H, Ar‐H), 7.03 (s, 1H, pyrimidine‐ 1H, ArCH=CH), 2.58 (s, 3H, Ar‐CH3), 2.41 (s, 6H, pyrimidine‐CH3), 2.31
H), 6.69 (d, J = 16.07 Hz, 1H, ArCH=CH), 3.74 (s, 3H, COOCH3), 2.62 (s, (p, J = 7.34 Hz, 2H, =CHCH2CH3), 1.03 (t, J = 7.38 Hz, 3H, =CHCH2CH3).
3H, Ar‐CH3), 2.41 (s, 6H, pyrimidine‐CH3). 13C NMR (101 MHz, DMSO‐ 13C NMR (101 MHz, DMSO‐d6) δ 167.72, 156.48, 148.82, 135.80,
d6) δ 168.24, 166.80, 156.96, 149.40, 143.11, 139.25, 138.38, 133.76, 135.07, 134.63, 133.42, 132.56, 129.89, 127.39, 126.39, 114.80,
132.83, 132.79, 130.60, 119.68, 115.34, 52.08, 23.69, 19.76. HRMS 23.19, 21.38, 18.92, 14.06. HRMS for C18H22N4O3S: calcd 375.1485
for C18H20N4O5S: calcd 405.1227 [M+H], found 405.1225.
[M+H], found 375.1486.
(Z)‐N‐((4,6‐dimethoxypyrimidin‐2‐yl)carbamoyl)‐2‐methyl‐5‐(prop‐ (Z)‐5‐(but‐1‐en‐1‐yl)‐2‐methyl‐N‐((4‐methylpyrimidin‐2‐
1‐en‐1‐yl)benzenesulfonamide (9f). white solid, yield 80.9%, m.p. yl)carbamoyl)benzenesulfonamide (9k). white solid, yield 76.8%,
1
147 – 148 °C.1H NMR (400 MHz, CDCl3) δ 12.65 (s, 1H, SO2NHCONH), m.p. 161 – 162 °C. H NMR (400 MHz, DMSO‐d6) δ 13.08 (s, 1H,
8.15 (s, 1H, Ar‐H), 7.42 (d, J = 8.08 Hz, 1H, Ar‐H), 7.27 (d, J = 7.71 Hz, SO2NHCONH), 10.67 (s, 1H, SO2NHCONH), 8.57 (d, J = 5.11 Hz, 1H,
1H, Ar‐H), 7.20 (s, 1H, SO2NHCONH), 6.43 (d, J = 12.44 Hz, 1H, pyrimidine‐H), 7.93 (s, 1H, Ar‐H), 7.49 (d, J = 7.70 Hz, 1H, Ar‐H), 7.42
ArCH=CH, cis alkene), 6.38 – 5.82 (m, 1H, ArCH=CH), 5.80 (s, 1H, (d, J = 7.86 Hz, 1H, Ar‐H), 7.13 (d, J = 5.11 Hz, 1H, pyrimidine‐H), 6.44
pyrimidine‐H), 3.96 (s, 6H, pyrimidine‐OCH3), 2.66 (s, 3H, Ar‐CH3), (d, J = 11.51 Hz, 1H, ArCH=CH, cis alkene), 5.75 (dt, J = 11.64, 7.36 Hz,
1.92 (d, J = 7.24 Hz, 3H, =CHCH3). 13C NMR (101 MHz, DMSO‐d6) δ 1H, ArCH=CH), 2.57 (s, 3H, Ar‐CH3), 2.46 (s, 3H, pyrimidine‐CH3), 2.30
171.14, 156.02, 148.43, 136.62, 135.06, 134.75, 133.59, 132.53, (p, J = 7.16 Hz, 2H, =CHCH2CH3), 1.03 (t, J = 7.47 Hz, 3H, =CHCH2CH3).
130.27, 127.83, 127.44, 83.68, 54.60, 19.16, 14.31. HRMS for 13C NMR (101 MHz, DMSO‐d6) δ 169.13, 158.04, 157.17, 149.27,
C17H20N4O5S: calcd 393.1227 [M+H], found 393.1229.
N‐((4,6‐dimethylpyrimidin‐2‐yl)carbamoyl)‐2‐methyl‐5‐
137.40, 136.31, 135.59, 135.23, 133.92, 133.05, 130.41, 126.92,
116.07, 23.98, 21.87, 19.54, 14.56. HRMS for C17H20N4O3S: calcd
vinylbenzenesulfonamide (9g). white solid, yield 78.1%, m.p. 168 – 361.1329 [M+H], found 361.1322.
169 °C.1H NMR (400 MHz, DMSO‐d6) δ 13.40 (s, 1H, SO2NHCONH), Ethyl
(E)‐3‐(3‐(N‐((4,6‐dimethoxypyrimidin‐2‐
10.59 (s, 1H, SO2NHCONH), 8.03 (s, 1H, Ar‐H), 7.76 (d, J = 7.83 Hz, 1H, yl)carbamoyl)sulfamoyl)‐4‐methylphenyl)acrylate (9l). white solid,
Ar‐H), 7.42 (d, J = 7.94 Hz, 1H, Ar‐H), 7.02 (s, 1H, pyrimidine‐H), 6.84 yield 73.3%, m.p. 170 –171 °C. 1H NMR (400 MHz, DMSO‐d6) δ 12.79
(dd, J = 17.64, 10.97 Hz, 1H, ArCH=CH2), 5.90 (d, J = 17.65 Hz, 1H, (s, 1H, SO2NHCONH), 10.62 (s, 1H, SO2NHCONH), 8.24 (s, 1H, Ar‐H),
ArCH=CH2), 5.38 (d, J = 10.97 Hz, 1H, ArCH=CH2), 2.58 (s, 3H, Ar‐CH3), 8.04 (d, J = 7.39 Hz, 1H, Ar‐H), 7.75 (d, J = 16.04 Hz, 1H, ArCH=CH,
2.40 (s, 6H, pyrimidine‐CH3). 13C NMR (101 MHz, DMSO‐d6) δ 168.24, trans alkene), 7.51 (d, J = 7.83 Hz, 1H, Ar‐H), 6.70 (d, J = 16.12 Hz, 1H,
156.98, 149.28, 137.89, 136.40, 135.86, 135.49, 133.43, 131.03, ArCH=CH), 6.03 (s, 1H, pyrimidine‐H), 4.20 (q, J = 6.96 Hz, 2H,
128.48, 116.28, 115.32, 23.70, 19.48. HRMS for C16H18N4O3S: calcd COOCH2CH3), 3.92 (s, 6H, pyrimidine‐OCH3), 2.62 (s, 3H, Ar‐CH3), 1.27
347.1172 [M+H], found 347.1175.
(t, J = 6.97 Hz, 3H, COOCH2CH3). 13C NMR (101 MHz, CDCl3) δ 171.22,
2‐methyl‐N‐((4‐methylpyrimidin‐2‐yl)carbamoyl)‐5‐
166.33, 155.35, 148.97, 142.03, 139.53, 137.63, 133.39, 132.74,
vinylbenzenesulfonamide (9h). white solid, yield 90.0%, m.p. 186 – 132.15, 130.61, 119.48, 84.95, 60.65, 54.72, 19.95, 14.30. HRMS for
187 °C.1H NMR (400 MHz, DMSO‐d6) δ 13.08 (s, 1H, SO2NHCONH), C19H22N4O7S: calcd 451.1282[M+H], found 451.1277.
10.67 (s, 1H, SO2NHCONH), 8.57 (s, 1H, pyrimidine‐H), 8.05 (s, 1H, Ar‐ Ethyl
(E)‐3‐(3‐(N‐((4,6‐dimethylpyrimidin‐2‐
H), 7.75 (s, 1H, Ar‐H), 7.42 (s, 1H, Ar‐H), 7.13 (s, 1H, pyrimidine‐H), yl)carbamoyl)sulfamoyl)‐4‐methylphenyl)acrylate (9m). white solid,
6.93 – 6.71 (m, 1H, ArCH=CH2), 5.91 (d, J = 17.07 Hz, 1H, ArCH=CH2), yield 80.5%, m.p. 162 – 163 °C. 1H NMR (400 MHz, CDCl3) δ 13.17 (s,
5.37 (d, J = 8.69 Hz, 1H, ArCH=CH2), 2.58 (s, 3H, Ar‐CH3), 2.46 (s, 3H, 1H, SO2NHCONH), 8.37 (s, 1H, SO2NHCONH), 7.93 (s, 1H, Ar‐H), 7.70
pyrimidine‐CH3). 13C NMR (101 MHz, DMSO‐d6) δ 169.17, 157.99, (d, J = 16.04 Hz, 1H, ArCH=CH, trans alkene), 7.64 (d, J = 7.87 Hz, 1H,
157.15, 149.26, 137.91, 136.48, 135.85, 135.50, 133.41, 131.02, Ar‐H), 7.33 (d, J = 7.76 Hz, 1H, Ar‐H), 6.79 (s, 1H, pyrimidine‐H), 6.52
128.52, 116.26, 116.06, 23.98, 19.60. HRMS for C15H16N4O3S: calcd (d, J = 16.03 Hz, 1H, ArCH=CH), 4.28 (q, J = 7.09 Hz, 2H, COOCH2CH3),
333.1016 [M+H], found 333.1019.
(Z)‐5‐(but‐1‐en‐1‐yl)‐N‐((4,6‐dimethoxypyrimidin‐2‐yl)carbamoyl)‐
2.71 (s, 3H, Ar‐CH3), 2.49 (s, 6H, pyrimidine‐CH3), 1.36 (t, J = 7.12 Hz,
3H, COOCH2CH3). 13C NMR (101 MHz, CDCl3) δ 166.56, 156.33, 149.04,
2‐methylbenzenesulfonamide (9i). white solid, yield 75.2 %, m.p. 142.41, 139.12, 137.96, 133.05, 132.95, 132.32, 130.59, 119.84,
126 – 127 °C.1H NMR (400 MHz, CDCl3) δ 12.67 (s, 1H, SO2NHCONH), 115.33, 60.68, 23.73, 20.10, 14.30. HRMS for C19H22N4O5S: calcd
8.14 (s, 1H, Ar‐H), 7.41 (d, J = 7.77 Hz, 1H, Ar‐H), 7.30 – 7.22 (m, 2H, 419.1384[M+H], found 419.1388.
Ar‐H and SO2NHCONH), 6.40 (d, J = 11.20 Hz, 1H, ArCH=CH, cis
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