Molecules 2015, 20
12040
8
1
.91 (s, 1H, NH), ppm; 13C-NMR (DMSO-d
6
, 125 MHz) δ 45.01, 50.73, 107.79, 113.70, 113.76,
19.61, 124.16, 128.70, 130.79, 138.30, 141.43, 145.69, 148.25, 149.24, 156.08, 158.07, 159.38 ppm;
S, C 52.44, H 4.19, N 17.67%.
anal. C 53.33, H 4.48, N 17.77%. calcd for C21
H
21ClN
6
O
3
N-(Phenylcarbamoyl)-4-(3,4,5-trimethyl-1H-pyrazol-1-yl)-3-pyridinesulfonamide (24). Starting from
-(3,4,5-trimethyl-1H-pyrazol-1-yl)-3-pyridinesulfonamide (9, 0.27 g), and phenyl isocyanate (0.14 g),
the title compound 24 was obtained (0.33 g, 87%): mp 161–164 °C; IR (KBr) νmax 3254, 3199 (NH), 3079,
4
−
1
3
018 (CAr-H), 2927, 2860 (C-H), 1730 (C=O), 1583, 1499 (C=C, C=N), 1363, 1350, 1170 (SO
1H-NMR (DMSO-d
, 200 MHz) δ 1.93 (s, 3H, CH ), 2.05 (s, 3H, CH ), 2.17 (s, 3H, CH ), 7.04 (t, 1H,
H-4 Ph), 7.28 (m, 4H, Ph), 7.57 (d, J = 5.2 Hz, 1H H-5 pyrid.), 8.96 (d, J = 5.2 Hz, 1H, H-6 pyrid.),
2
) cm ;
6
3
3
3
1
3
9
.08 (s, 1H, H-2 pyrid.), 9.27 (s, 1H, NH), 9.7 (br.s, 1H, NH), ppm; C-NMR (DMSO-d
δ 8.56, 10.61, 12.64, 114.15, 119.43, 124.07, 124.21, 129.65, 132.08, 138.48, 144.97, 149.67, 150.12,
52.88, 155.93 ppm; anal. C 56.09, H 4.97, N 18.17%. calcd for C18 S, C 55.78, H 4.89,
N 18.18%.
6
, 125 MHz)
1
H
19
N
5
O
3
N-[(4-Chlorophenyl)carbamoyl]-4-(3,4,5-trimethyl-1H-pyrazol-1-yl)-3-pyridinesulfonamide
(25).
Starting from 4-(3,4,5-trimethyl-1H-pyrazol-1-yl)-3-pyridinesulfonamide (9, 0.27 g), and 4-chloro-
phenyl isocyanate (0.18 g), the title compound 25 was obtained (0.31 g, 75%): mp 178–182 °C; IR
(
(
(
KBr) νmax 3247, 3186 (NH), 3010, 3035 (CAr-H), 2992, 2862 (C-H), 1727 (C=O), 1588, 1552, 1496
−1 1
C=C, C=N), 1384, 1363, 1170 (SO
s, 3H, CH ), 2.16 (s, 3H, CH ), 7.35 (s, 4H, Ph), 7.57 (d, 1H H-5 pyrid.), 8.96 (d, 1H, H-6 pyrid.),
.21 (s, 1H, H-2 pyrid.), 9.26 (s, 1H, NH), ppm; C-NMR (DMSO-d
13.75, 120.69, 123.83, 127.29, 129.11, 131.64, 137.07, 138.09, 144.56, 149.28, 149.72, 152.40,
55.57 ppm; anal. C 51.49, H 4.32, N 16.68%. calcd for C18 S, C 51.22, H 4.20, N 16.57%.
2
) cm ; H-NMR (DMSO-d
6
, 200 MHz) δ 1.93 (s, 3H, CH
3
), 2.05
3
3
1
3
9
1
1
6
, 50 MHz) δ 8.13, 10.19, 12.21,
H18ClN
5
O
3
N-[(3,4-Dichlorophenyl)carbamoyl]-4-(3,4,5-trimethyl-1H-pyrazol-1-yl)-3-pyridinesulfonamide (26).
Starting from 4-(3,4,5-trimethyl-1H-pyrazol-1-yl)-3-pyridinesulfonamide (9, 0.27 g), and 3,4-dichloro-
phenyl isocyanate (0.23 g), the title compound 26 was obtained (0.25 g, 55%): mp 163–166 °C; IR
(
KBr) νmax 3324 (NH), 3104 (CAr-H), 2924, 2856 (C-H), 1727 (C=O), 1599, 1581, 1477 (C=C, C=N),
−1 1
1
381 1169 (SO
2
) cm ; H-NMR (DMSO-d
6
, 200 MHz) δ 1.92 (s, 3H, CH
3
), 2.04 (s, 3H, CH ), 2.14
3
(
s, 3H, CH
3
), 7.25 (dd, 1H, H-6 Ph), 7.55 (m, 2H, H-5 Ph, H-5 pyrid.), 7.69 (d, 1H H-2 Ph), 8.96 (d,
1
3
1
H, H-6 pyrid.), 9.26 (s, 1H, H-2 pyrid.), 9.40 (s, 1H, NH), ppm; C-NMR (DMSO-d , 125 MHz)
6
δ 8.55, 10.60, 12.64, 114.16, 119.69, 120.63, 124.29, 125.50, 131.48, 131.85, 132.12, 138.51, 138.78,
44.96, 149.97, 150.13, 152.75, 156.00 ppm; anal. C 47.58, H 3.77, N 15.41% calcd for C18 S,
C 47.45, H 3.81, N 15.38%.
1
H17Cl N O
2 5 3
4
-(4-Butyl-3,5-dimethyl-1H-pyrazol-1-yl)-N-[(4-chlorophenyl)carbamoyl]-3-pyridinesulfonamide (27).
Starting from 4-(4-butyl-3,5-dimethyl-1H-pyrazol-1-yl)-3-pyridinesulfonamide (10, 0.31 g), and
-chlorophenyl isocyanate (0.18 g), the title compound 27 was obtained (0.35 g, 76%): m.p.
4
(
EtOAc/Et
2
O). 138–142 °C ; IR (KBr) νmax 3344 (NH), 3127, (CAr-H), 2947, 2865 (C-H), 1726 (C=O),
−1 1
1
602, 1579, 1541, 1495 (C=C, C=N), 1385, 1164 (SO
2
) cm ; H-NMR (DMSO-d
), 2.19 (s, 3H, CH ), 2.36 (t, 2H, CH
s, 4H, Ph), 7.60 (d, 1H H-5 pyrid.), 8.96 (d, 1H, H-6 pyrid.), 9.25 (s, 1H, H-2 pyrid.), 9.27 (s, 1H, NH),
6
, 200 MHz) δ 0.90
(t, 3H, CH
3
), 1.36 (m, 4H, 2 × CH
2
), 2.07 (s, 3H, CH
3
3
2
), 7.36
(