928
M. KRASAVIN ET AL.
Anal. calcd for C12H16N4O4S2 (344.41): C, 41.85; H, 4.68; N, 16.27; S, [M þ H]þ 365.8. Anal. calcd for C11H13ClN4O4S2 (264.83): C, 36.21;
18.62; found: C, 41.81; H, 4.68; N, 16.31; S, 18.62.
H, 3.59; N, 15.36; S, 17.58; found: C, 36.18; H, 3.59; N, 15.33; S,
13.59.
1-(2-Methyl-5-sulfamoylphenyl)-1H-pyrazole-4-sulfonamide (9i)
Prepared from 6g according to GP2; white solid, m.p. 185–188 ꢀC
(i-PrOH), yield 47%. 1H NMR (400 MHz, DMSO-d6) d ppm 8.60 (s,
1H, Hpyrazole), 8.05 (s, 1H, Hpyrazole), 7.84 (dd, J3–4 ¼ 7.8 Hz,
J4–6 ¼ 1.7 Hz, 1H, 4-HAr), 7.80 (d, J4–6 ¼ 1.3 Hz, 1H, 6-HAr), 7.64 (d,
J3–4 ¼ 7.8 Hz, 1H, 3-HAr), 7.44 (s, 2H, SO2NH2), 7.41 (s, 2H, SO2NH2),
2.32 (m, 3H, CH3). 13C NMR (75 MHz, DMSO-d6) d ppm 143.3, 139.1,
137.6, 132.6, 132.5, 128.7, 128.6, 126.3, 123.8, 18.2. LC/MS (ESIþ):
m/z [M þ H]þ 317.4. Anal. calcd for C10H11N3O2S (316.36): C, 37.97;
H, 3.82; N, 17.71; S, 20.27; found: C, 37.92; H, 3.83; N, 17.75; S,
20.30.
1-(4-Chloro-3-sulfamoylphenyl)-1H-pyrazole-4-sulfonamide (9n)
Prepared from 6o according to GP2; white solid, m.p. 232–235 ꢀC
(AcOEt), yield 21%. 1H NMR (400 MHz, DMSO-d6) d ppm 9.07 (s,
1H,
H
pyrazole), 8.48 (d, J2–6 ¼ 2.7 Hz, 1H, 2-HAr), 8.15 (dd,
J5–6 ¼ 8.8 Hz, J2–6 ¼ 2.7 Hz, 1H, 6-HAr), 8.09 (s, 1H, Hpyrazole), 7.81 (d,
J5–6 ¼ 8.8 Hz, 1H, 5-HAr), 7.79 (s, 2H, SO2NH2), 7.47 (s, 2H, SO2NH2).
13C NMR (75 MHz, DMSO-d6) d ppm 142.7, 139.9, 137.8, 133.3,
130.1, 129.2, 129.1, 123.4, 120.0. LC/MS (ESIþ): m/z [M þ H]þ 337.8.
Anal. calcd for C9H9ClN4O4S2 (336.78): C, 32.10; H, 2.69; N, 16.64; S,
19.04; found: C, 32.05; H, 2.70; N, 16.69; S, 19.05.
1-(3-Chloro-4-sulfamoylphenyl)-3,5-dimethyl-1H-pyrazole-4-sulfona-
mide (9o)
1-(4-Methoxy-3-sulfamoylphenyl)-3,5-dimethyl-1H-pyrazole-4-sul-
fonamide (9j)
Prepared from 6r according to GP2; white solid, m.p. 198–201 ꢀC
(AcOEt), yield 43%. 1H NMR (300 MHz, DMSO-d6) d ppm 7.86 (d,
J2–6 ¼ 2.4 Hz, 1H, X-HAr), 7.80 (d, J5–6 ¼ 8.6 Hz, 1H, A-HAr), 7.54 (dd,
J5–6 ¼ 8.6, J2–6 ¼ 2.4 Hz, 1H, B-HAr), 7.29 (s, 2H, in exchange,
SO2NH2), 2.46 (s, 3H, CH3), 2.36 (s, 3H, CH3). 13C NMR (75 MHz,
DMSO-d6) d ppm 147.9, 141.3, 138.5, 132.2, 131.6, 131.5, 127.5,
125.9, 122.5, 13.4, 11.9. LC/MS (ESIþ): m/z [M þ H]þ 365.8. Anal.
calcd for C11H13ClN4O4S2 (264.83): C, 36.21; H, 3.59; N, 15.36; S,
17.58; found: C, 36.19; H, 3.59; N, 15.35; S, 13.58.
Prepared from 6j according to GP2; white solid, m.p. 254–257ꢀC (i-
1
PrOH), yield 79%. H NMR (400 MHz, DMSO-d6) d ppm 7.72 (m, 2H,
2-HAr, 6-HAr), 7.35 (d, J5–6 ¼ 8.6 Hz, 1H, 5-HAr), 7.29 (s, 2H, SO2NH2),
7.22 (s, 2H, SO2NH2), 3.97 (s, 3H, OCH3), 2.36 (s, 3H, CH3), 2.40 (s,
3H, CH3). 13C NMR (75 MHz, DMSO-d6) d ppm 156.3, 147.4, 141.1,
132.4, 130.9, 130.7, 125.4, 121.8, 113.9, 57.1, 13.4, 11.8. LC/MS
(ESIþ): m/z [M þ H]þ 361.4. Anal. calcd for C12H16N4O5S2 (360.41):
C, 39.99; H, 4.47; N, 15.55; S, 17.79; found: C, 39.94; H, 4.48; N,
15.52; S, 17.81.
1-(3-Chloro-4-sulfamoylphenyl)-1H-pyrazole-4-sulfonamide (9p)
Prepared from 6q according to GP2; white solid, m.p. 195–197 ꢀC
(AcOEt), yield 25%. 1H NMR (400 MHz, DMSO-d6) d ppm 9.07 (s,
1H, Hpyrazole), 8.23 (d, J2–6 ¼ 2.3 Hz, 1H, 2-HAr), 8.06 (s, 1H, Hpyrazole),
7.78 (dd, J5–6 ¼ 8.6 Hz, J2–6 ¼ 2.3 Hz, 1H, 6-HAr),7.94 (d, J5–6 ¼ 8.6 Hz,
1H, 5-HAr), 7.42 (s, 4H, 2 x SO2NH2). 13C NMR (75 MHz, DMSO-d6) d
ppm 139.8, 138.9, 132.6, 132.0, 130.1, 129.9, 129.3, 121.2, 119.5.
LC/MS (ESIþ): m/z [M þ H]þ 337.8. Anal. calcd for C9H9ClN4O4S2
(336.78): C, 32.10; H, 2.69; N, 16.64; S, 19.04; found: C, 32.07; H,
2.69; N, 16.66; S, 19.04.
1-(3-Methoxy-4-sulfamoylphenyl)-3,5-dimethyl-1H-pyrazole-4-sul-
fonamide (9k)
Prepared from 6l according to GP2; white solid, m.p. 256–258 ꢀC
(i-PrOH), yield 82%. 1H NMR (400 MHz, DMSO-d6) d ppm 7.85 (d,
J5–6 ¼ 8.3 Hz, 1H, 5-HAr), 7.32 (d, J2–6 ¼ 1.8 Hz, 1H, 2-HAr), 7.28 (s,
2H, SO2NH2), 7.22 (s, 1H, SO2NH2), 7.19 (dd, J5–6 ¼ 8.3 Hz,
J2–6 ¼ 1.8 Hz, 1H, 6-HAr), 3.95 (s, 3H, OCH3), 2.50 (s, 3H, CH3), 2.36
(m, 3H, CH3). 13C NMR (75 MHz, DMSO-d6) d ppm 157.02, 147.82,
142.86, 141.29, 131.42, 128.96, 122.60, 116.84, 110.34, 57.11, 13.47,
12.15. LC/MS (ESIþ): m/z [M þ H]þ 361.4.
1-(2-Chloro-5-sulfamoylphenyl)-3,5-dimethyl-1H-pyrazole-4-sulfona-
mide (9q)
1-(2-Methoxy-5-sulfamoylphenyl)-3,5-dimethyl-1H-pyrazole-4-sul-
fonamide (9l)
Prepared from 6t according to GP2; white solid, m.p. 230–232 ꢀC
(AcOEt), yield 41%. 1H NMR (400 MHz, DMSO-d6) d ppm 8.00 (dd,
J3–4 ¼ 8.3 Hz, J4–6 ¼ 1.7 Hz, 1H, 4-HAr), 7.94 (d, J3–4 ¼ 8.3 Hz, 1H, 3-
HAr), 7.91 (d, J4–6 ¼ 1.7 Hz, 1H, 6-HAr), 7.57 (s, 2H, SO2NH2), 7.28 (s,
2H, SO2NH2), 2.38 (s, 3H, CH3), 2.26 (s, 3H, CH3). 13C NMR (75 MHz,
DMSO-d6) d ppm 148.1, 144.6, 142.5, 136.3, 135.0, 131.8, 128.9,
127.7, 121.8, 13.4, 11.3. LC/MS (ESIþ): m/z [M þ H]þ 365.8. Anal.
calcd for C11H13ClN4O4S2 (264.83): C, 36.21; H, 3.59; N, 15.36; S,
17.58; found: C, 36.15; H, 3.60; N, 15.29; S, 13.60.
Prepared from 6n according to GP2; white solid, m.p. 238–242 ꢀC
(i-PrOH), yield 68%. 1H NMR (400 MHz, DMSO-d6) d ppm 7.95 (dd,
J3–4 ¼ 8.8 Hz, J4–6 ¼ 2.4 Hz, 1H, 4-HAr), 7.73 (d, J4–6 ¼ 2.4 Hz, 1H, 6-
HAr), 7.44 (d, J3–4 ¼ 8.8 Hz, 1H, 3-HAr), 7.36 (s, 2H, SO2NH2), 7.24
(s, 2H, SO2NH2), 3.88 (s, 3H, OCH3), 2.35 (s, 3H, CH3), 2.21 (s, 3H,
CH3); 13C NMR (75 MHz, DMSO-d6) d ppm 156.8, 147.5, 142.7,
137.0, 129.1, 127.1, 127.0, 121.3, 113.5, 57.0, 13.4, 11.3. LC/MS
(ESIþ): m/z [M þ H]þ 361.4. Anal. calcd for C12H16N4O5S2 (360.41):
C, 39.99; H, 4.47; N, 15.55; S, 17.79; found: C, 39.91; H, 4.48; N,
15.60; S, 17.82.
1-(2-Chloro-5-sulfamoylphenyl)-1H-pyrazole-4-sulfonamide (9r)
Prepared from 6s according to GP2; white solid, m.p. 235–237 ꢀC
(AcOEt), yield 31%. 1H NMR (400 MHz, DMSO-d6) d ppm 8.71 (s,
1H, Hpyrazole), 8.10 (s, 1H, Hpyrazole), 8.00 (m, 1H, HAr), 7.94 (m, 2H,
HAr), 7.39 (s, 4H, 2 x SO2NH2). 13C NMR (75 MHz, DMSO-d6) d ppm
140.1, 139.4, 132.8, 132.4, 130.1, 130.1, 128.9, 120.9, 118.9. LC/MS
(ESIþ): m/z [M þ H]þ 337.8. Anal. calcd for C9H9ClN4O4S2 (336.78):
1-(4-Chloro-3-sulfamoylphenyl)-3,5-dimethyl-1H-pyrazole-4-sulfona-
mide (9m)
Prepared from 6p according to GP2; white solid, m.p. 241–243 ꢀC
(AcOEt), yield 39%. 1H NMR (400 MHz, DMSO-d6) d ppm 8.02
(d, J2–6 ¼ 2.0 Hz, 1H, 2-HAr), 7.80 (m, 4H, 5-HAr, 6-HAr, SO2NH2),
7.29 (s, 2H, SO2NH2), 2.47 (s, 3H, CH3), 2.37 (m, 3H, CH3).
13C NMR (75 MHz, DMSO-d6) d ppm 148.1, 142.4, 141.4, 137.4, C, 32.10; H, 2.69; N, 16.64; S, 19.04; found: C, 32.05; H, 2.70; N,
133.0, 130.4, 129.7, 125.9, 122.7, 13.4, 12.0. LC/MS (ESIþ): m/z 16.69; S, 19.05.