NOVEL 3ꢀPYRIDINECARBONITRILES INCORPORATING SULFONAMIDE MOIETIES
445
1624 (C=N), 1338, 1151 (SO2). 1H NMR: 2.6 (s, 3H,
CH3), 6.6–8.4 (m, 13H, ArꢀH), 8.9 (s, 1H, SO2NH,
exchangeable with D2O), 10.8 (s, 1H, NH, exchangeꢀ
able with D2O). 13C NMR: 24.7, 112.7, 112.9, 114.3 (2),
116.0, 117.0, 119.1 (2), 125.2, 128.4 (2), 129.7 (2),
130.2, 135.1 (2), 142.4, 149.3 (2), 153.5, 160.8. MS,
m/z
(%): 430 (M+) (1.7470), 269 (100). Calcd. for
C22H18N6O2S (430.48): C, 61.38; H, 4.21; N, 19.52.
Found: C, 61.07; H, 4.56; N, 19.19.
4ꢀ(3ꢀCyanoꢀ6ꢀmethylpyridinꢀ2ꢀylamino)ꢀ
thylisoxazolꢀ5ꢀyl)benzenesulfonamide (VI). Yield 68%;
mp >300 C. IR: 3314, 3165 (NH), 3067 (CH arom.),
2954, 2843 (CH aliph.), 2221 (C
Nꢀ(3ꢀmeꢀ
°
≡
N), 1632 (C=N),
1365, 1155 (SO2). 1H NMR: 2.3, 2.4 (2s, 6H, 2CH3),
6.5 (s, 1H, CH isoxazole), 7.0–8.3 (m, 6H, ArꢀH), 9.0
(s, 1H, SO2NH, exchangeable with D2O), 10.9 (s, 1H,
13
NH, exchangeable with D2O). C NMR: 14.1, 22.6,
98.9, 109.4, 112.7 (2), 113.0, 114.6, 127.7, 129.2 (2),
139.5, 145.8, 152.2, 159.0, 160.6, 161.9. MS, m/z (%):
4ꢀ(3ꢀCyanoꢀ6ꢀmethylpyridinꢀ2ꢀylamino)ꢀ
dinꢀ2ꢀyl)benzenesulfonamide (XI). Yield 80%; mp
269.8 C. IR: 3417, 3309 (NH), 3066 (CH arom.),
2948, 2839 (CH aliph.), 2202 (C
Nꢀ(pyriꢀ
369 (M+) (34.1193), 273 (100). Calcd. for
C17H15N5O3S (369.40): C, 55.27; H, 4. 09; N, 18.96.
Found: C, 54.88; H, 4.31; N, 19.23.
°
≡
N), 1583 (C=N),
1367, 1137 (SO2). 1H NMR: 2.5 (s, 3H, CH3), 6.7–8.5
(m, 10H, ArꢀH), 8.9 (s, 1H, SO2NH, exchangeable
with D2O), 10.6 (s, 1H, NH, exchangeable with D2O).
13C NMR: 21.8, 110.6, 111.3, 112.7 (2), 113.4, 114.0,
115.8, 127.1, 129.3 (2), 140.7, 141.3, 143.6, 146.9,
4ꢀ(3ꢀCyanoꢀ6ꢀmethylpyridinꢀ2ꢀylamino)ꢀ
dimethylisoxazolꢀ5ꢀyl)benzenesulfonamide (VII). Yield
76%; mp >300 C. IR: 3383, 3263 (NH), 3091 (CH
arom.), 2972, 2927 (CH aliph.), 2273 (C N), 1625
Nꢀ(3,4ꢀ
°
≡
1
(C=N), 1338, 1145 (SO2). H NMR: 2.37, 2.39 (2s,
6H, 2CH3 isoxazole), 2.6 (s, 3H, CH3), 6.6–8.3 (m,
6H, ArꢀH), 8.9 (s, 1H, SO2NH, exchangeable with
D2O), 10.8 (s, 1H, NH, exchangeable with D2O).
153.6, 155.5, 162.0. MS,
m/z
(%): 365 (M+)
(37.4632), 286 (100). Calcd. for C18H15N5O2S
(365.41): C, 59.16; H, 4.14; N, 19.17. Found: C,
59.47; H, 4.46; N, 19.53.
13C NMR: 8.2, 12.6, 22.4, 99.1, 110.4, 114.6 (2),
115.7, 117.3, 128.6, 129.7 (2), 144.0, 146.3, 154.8,
160.3, 163.5 (2). MS, m/z
(%): 383 (M+) (9.2146), 91
(100). Calcd. for C18H17N5O3S (383.42): C, 56.38; H,
4. 47; N, 18.27. Found: C, 56.66; H, 4.18; N, 18.57.
4ꢀ(3ꢀCyanoꢀ6ꢀmethylpyridinꢀ2ꢀylamino)ꢀ
midinꢀ2ꢀyl)benzenesulfonamide (XII). Yield 79%; mp
261.6 C. IR: 3358, 3257 (NH), 3051 (CH arom.),
2981, 2839 (CH aliph.), 2218 (C
Nꢀ(pyriꢀ
°
≡
N), 1595 (C=N),
1408, 1157 (SO2). 1H NMR: 2.7 (s, 3H, CH3), 6.8–8.8
(m, 9H, ArꢀH), 10.6 (s, 1H, SO2NH, exchangeable
with D2O), 12.0 (s, 1H, NH, exchangeable with D2O).
13C NMR: 24.6, 112.7 (2), 116.9, 119.1 (2), 127.5,
129.1 (2), 142.7, 143.3, 153.8, 160.7 (2), 162.7, 163.0.
MS, m/z
(%): 366 (M+) (19.4404), 271 (100). Calcd.
for C17H14N6O2S (366.40): C, 55.73; H, 3.85; N,
22.94. Found: C, 55.45; H, 4.21; N, 23.31.
4ꢀ(3ꢀCyanoꢀ6ꢀmethylpyridinꢀ2ꢀylamino)ꢀ
zolꢀ2ꢀyl)benzenesulfonamide (VIII). Yield 84%; mp
183.3 C. IR: 3363, 3219 (NH), 3099 (CH arom.),
2963, 2870, 2779 (CH aliph.), 2215 (C N), 1595
Nꢀ(thiaꢀ
°
≡
1
(C=N), 1406, 1138 (SO2). H NMR: 2.3 (s, 3H,
CH3), 6.5–8.2 (m, 8H, ArꢀH), 8.9 (s, 1H, SO2NH, exꢀ
changeable with D2O), 10.7 (s, 1H, NH, exchangeable
13
with D2O). C NMR: 25.1, 112.5, 112.7, 113.0 (2),
114.1, 117.5, 126.2, 129.3 (2), 136.6, 139.2, 144.9, 152.8,
4ꢀ(3ꢀCyanoꢀ6ꢀmethylpyridinꢀ2ꢀylamino)ꢀ
methylpyrimidinꢀ2ꢀyl)benzenesulfonamide (XII). Yield
84%; mp 259.9 C. IR: 3495, 3379 (NH), 3078 (CH
N), 1627
Nꢀ(4ꢀ
160.0, 168.7. MS,
m/z
(%): 371 (M+) (4.5908), 292
(100). Calcd. for C16H13N5O2S2 (371.44): C, 51.74; H,
3.53; N, 18.85. Found: C, 51.47; H, 3.21; N, 18.52.
°
arom.), 2956, 2873 (CH aliph.), 2210 (C
≡
(C=N), 1371, 1190 (SO2). 1H NMR: 2.5 (s, 3H, CH3
pyrimidine), 2.7 (s, 3H, CH3), 6.7–8.5 (m, 8H, ArꢀH),
8.6 (s, 1H, SO2NH, exchangeable with D2O), 10.7 (s, 1H,
4ꢀ(3ꢀCyanoꢀ6ꢀmethylpyridinꢀ2ꢀylamino)ꢀ
methylꢀ1,3,4ꢀthiadiazolꢀ2ꢀyl)benzenesulfonꢀamide (IX).
Yield 82%; mp 243.9 C. IR: 3361, 3212 (NH), 3100
(CH arom.), 2922, 2871 (CH aliph.), 2208 (C N),
Nꢀ(5ꢀ
°
13
≡
NH, exchangeable with D2O). C NMR: 24.7, 25.2,
109.3, 111.3, 112.6 (2), 113.7, 114.3, 127.8, 128.1 (2),
143.4, 145.9, 153.0, 155.2, 161.3, 169.0, 172.6. MS,
m/z
(%): 380(M+) (34.1736), 364 (100). Calcd. for
C18H16N6O2S (380.42): C, 56.83; H, 4.24; N, 22.09.
Found: C, 56.48; H, 4.01; N, 21.88.
1595 (C=N), 1398, 1143 (SO2). 1H NMR: 2.6 (s, 3H,
CH3), 2.8 (s, 3H, CH3 thiadiazole), 6.7–8.4 (m, 6H,
ArꢀH), 8.8 (s, 1H, SO2NH, exchangeable with D2O),
10.8 (s, 1H, NH, exchangeable with D2O). 13C NMR:
19.0, 21.9, 112.6, 113.7 (2), 115.7, 116.2, 129.9, 130.2
(2), 143.8, 143.9, 145.3, 152.0, 161.3, 168.9. MS, m/z
4ꢀ(3ꢀCyanoꢀ6ꢀmethylpyridinꢀ2ꢀylamino)ꢀ
dimethylpyrimidinꢀ2ꢀyl)benzenesulfonamide (XIV).
Yield 90%; mp 186.5 C. IR: 3365, 3228 (NH), 3068
(CH arom.), 2924, 2854 (CH aliph.), 2208 (C N),
Nꢀ(4, 6ꢀ
(%): 386 (M+) (13.6236), 355 (100). Calcd. for
C16H14N6O2S2 (386.45): C, 49.73; H, 3.65; N, 21.75.
Found: C, 49.49; H, 3.31; N, 21.99.
°
≡
1595 (C=N), 1346, 1153 (SO2). 1H NMR: 2.3 (s, 3H,
CH3 pyrimidine), 2.5 (s, 3H, CH3), 6.7 (s, 1H, CH
pyrimidine), 6.9–8.4 (m, 6H, ArꢀH), 8.5 (s, 1H,
SO2NH, exchangeable with D2O), 10.6 (s, 1H, NH,
4ꢀ(3ꢀCyanoꢀ6ꢀmethylpyridinꢀ2ꢀylamino)ꢀ
phenylꢀ1 ꢀpyrazolꢀ5ꢀyl)benzenesulfonamide (X). Yield
72%; mp 225.1 C. IR: 3402, 3196 (NH), 3100
(CH arom.), 2975, 2861 (CH aliph.), 2200 (C N),
Nꢀ(1ꢀ
H
°
≡
RUSSIAN JOURNAL OF BIOORGANIC CHEMISTRY Vol. 42
No. 4
2016