Month 2019
Novel Triazole Sulfonamide Derivatives
HRMS (EI): C13H17FN6O4S2 (M)+ calcd. 404.0737; found
404.0737.
8.81 (d, 1H), 7.97 (d, 1H), 7.84 (d, 1H), 7.73 (dd, 1H),
7.65 (d, 1H), 7.56 (t, 1H), 4.91 (s, 2H), 3.05 (s, 6H),
2.84–2.79 (m, 1H), 0.87–0.83 (m, 2H), 0.75–0.70 (m,
2H). 13C-NMR: δ 163.02, 157.04, 147.40, 146.15,
136.98, 129.76, 128.96, 127.67, 127.38, 126.61, 119.97,
56.99, 38.90, 31.75, 7.39. HRMS (EI): C17H20N6O4S2
(M)+ calcd. 436.0987; found 436.0985.
N3-Cyclopropyl-N3-((3,5-dimethylisoxazol-4-yl)methyl)-N1,
N1-dimethyl-1H-1,2,4-triazole-1,3-disulfonamide
(6d).
1
White solid (80%). mp 106–108°C. H-NMR: δ (ppm)
8.63 (s, 1H), 4.38 (s, 2H), 3.09 (s, 6H), 2.58–2.55 (m,
1H), 2.42 (s, 3H), 2.31 (s, 3H), 0.86–0.83 (m, 2H), 0.78–
0.73 (m, 2H). 13C-NMR: δ 168.09, 162.92, 159.67,
146.16, 108.83, 43.92, 38.85, 30.73, 11.23, 10.32, 7.52.
HRMS (EI): C13H20N6O5S2 (M)+ calcd. 404.0937; found
404.0938.
N3-((1H-Pyrrol-2-yl)methyl)-N3-cyclopropyl-N1,N1-dimethyl-
1H-1,2,4-triazole-1,3-disulfonamide (6k).
White solid
1
(74%). mp 102–104°C. H-NMR: δ (ppm) 8.93 (s, 1H),
8.63 (s, 1H), 6.77 (s, 1H), 6.11 (s, 1H), 6.08 (s, 1H), 4.55
(s, 2H), 3.08 (s, 6H), 2.54–2.51 (m, 1H), 0.93–0.89 (m,
2H), 0.81–0.75 (m, 2H). 13C-NMR: δ 163.23, 146.22,
125.60, 118.90, 109.10, 107.97, 47.55, 38.90, 30.29,
7.42. HRMS (EI) C12H18N6O4S2 (M)+ calcd. 374.0831;
found 374.0832.
N3-Cyclopropyl-N1,N1-dimethyl-N3-((5-methylisoxazol-3-yl)
methyl)-1H-1,2,4-triazole-1,3-disulfonamide (6e).
White
1
solid (67%). mp 107–109°C. H-NMR: δ (ppm) 8.63 (s,
1H), 6.11 (s, 1H), 4.58 (s, 2H), 3.09 (s, 6H), 2.66–2.61
(m, 1H), 2.41 (s, 3H), 0.92–0.88 (m, 2H), 0.82–0.77 (m,
2H). 13C-NMR: δ 170.09, 162.85, 160.09, 146.13,
101.69, 46.14, 38.91, 31.05, 12.21, 7.53. HRMS (EI):
C12H18N6O5S2 (M)+ calcd. 390.0780; found 390.0783.
N3-Cyclopropyl-N1,N1-dimethyl-N3-((1-methyl-1H-pyrrol-2-
N3-Cyclopropyl-N1,N1-dimethyl-N3-(pyridin-3-ylmethyl)-1H-
1,2,4-triazole-1,3-disulfonamide (6l).
White solid (70%).
1
mp 98–101°C. H-NMR: δ (ppm) 8.64 (s, 1H), 8.37 (s,
1H), 8.16 (d, J = 4.4 Hz, 1H), 8.10–8.06 (m, 1H), 7.26–
7.24 (m, 1H), 4.62 (s, 2H), 3.08 (s, 6H), 2.64–2.59 (m,
1H), 0.86–0.82 (m, 2H), 0.82–0.74 (m, 2H). 13C-NMR: δ
162.88, 163.31, 148.16, 144.18, 140.49, 121.79, 119.76,
48.01, 38.95, 31.56, 7.51. HRMS (EI): C13H18N6O4S2
(M)+ calcd. 386.0831; found 386.0830.
yl)methyl)-1H-1,2,4-triazole-1,3-disulfonamide (6f).
White
solid (75%). mp 94–97°C. 1H-NMR: δ (ppm) 8.62 (s,
1H), 6.59 (s, 1H), 6.09 (s, 1H), 6.00 (s, 1H), 4.58 (s,
2H), 3.68 (s, 3H), 3.08 (s, 6H), 2.43–2.36 (m, 1H), 0.73–
0.68 (m, 4H). 13C-NMR: δ 162.81, 146.08, 125.25,
123.32, 111.38, 106.91, 46.81, 38.90, 34.07, 29.95, 7.18.
HRMS (EI): C13H20N6O4S2 (M)+ calcd. 388.0987; found
388.0984.
N3-Cyclopropyl-N1,N1-dimethyl-N3-((1-methyl-1H-pyrazol-4-
yl)methyl)-1H-1,2,4-triazole-1,3-disulfonamide (6m).
White
solid (68%). mp 90–91°C. 1H-NMR: δ (ppm) 8.55 (s,
1H), 7.34 (s, 1H), 7.30 (s, 1H), 4.42 (s, 2H), 3.81 (s,
3H), 3.05 (s, 6H), 2.59–2.54 (m, 1H), 0.96–0.92 (m, 2H),
0.84–0.80 (m, 2H). 13C-NMR: δ 163.81, 146.09, 131.89,
125.32, 115.38, 46.56, 44.07, 38.90, 29.09, 7.15. HRMS
(EI): C12H19N7O4S2 (M)+ calcd. 389.0940; found
N3-((4-Bromothiazol-2-yl)methyl)-N3-cyclopropyl-N1,N1-
dimethyl-1H-1,2,4-triazole-1,3-disulfonamide (6g).
White
solid (73%). mp 83–85°C. 1H-NMR: δ (ppm) 8.63 (s,
1H), 7.47 (s, 1H), 4.73 (s, 2H), 3.09 (s, 6H), 2.64–2.56
(m, 1H), 0.97–0.92 (m, 2H), 0.88–0.83 (m, 2H). 13C-
NMR: δ 162.88, 146.18, 142.47, 137.25, 137.20, 46.69,
38.91, 30.53, 7.75. HRMS (EI): C11H15BrN6O4S3 (M)+
calcd. 469.9500; found 469.9506.
389.0943.
N3-((5-Chlorobenzo[b]thiophen-3-yl)methyl)-N3-cyclopropyl-
N1,N1-dimethyl-1H-1,2,4-triazole-1,3-disulfonamide (6n).
1
White solid (68%). mp 183–187°C. H-NMR: δ (ppm)
N3-((5-Chlorothiophen-2-yl)methyl)-N3-cyclopropyl-N1,N1-
dimethyl-1H-1,2,4-triazole-1,3-disulfonamide (6h).
White
8.62 (s, 1H), 7.96 (s, 1H), 7.79 (d, 1H), 7.53 (s, 1H),
7.35 (d, 1H), 4.80 (s, 2H), 3.07 (s, 6H), 2.58–2.55 (m,
1H), 0.86–0.82 (m, 2H), 0.77–0.72 (m, 2H). 13C-NMR: δ
163.01, 146.04, 139.12, 138.53, 130.86, 130.32, 128.28,
125.10, 123.82, 121.69, 48.59, 38.90, 31.18, 7.59.
HRMS (EI): C16H18ClN5O4S3 (M)+ calcd. 475.0209;
found 475.0210.
1
solid (77%). mp 108–109°C. H-NMR: δ (ppm) 8.60 (s,
1H), 6.78 (d, 1H), 6.74 (d, 1H), 4.65 (s, 2H), 3.08 (s,
6H), 2.69–2.64 (m, 1H), 0.98–0.94 (m, 2H), 0.87–0.83
(m, 2H). 13C-NMR: δ 163.19, 146.03, 136.68, 130.39,
127.38, 125.81, 49.34, 38.90, 30.46, 7.82. HRMS (EI)
C12H16ClN5O4S3 (M)+ calcd. 425.0053; found 425.0051.
N3-((1H-Benzo[d]imidazol-2-yl)methyl)-N3-cyclopropyl-N1,
N1-dimethyl-1H-1,2,4-triazole-1,3-disulfonamide (6i). White
N3-(Benzo[d]thiazol-2-ylmethyl)-N3-cyclopropyl-N1,N1-
dimethyl-1H-1,2,4-triazole-1,3-disulfonamide (6o).
White
1
1
solid (70%). mp 111–114°C. H-NMR: δ (ppm) 9.40 (s,
solid (72%). mp 145–148°C. H-NMR: δ (ppm) 8.63 (s,
1H), 7.96 (d, 1H), 7.89 (d, 1H), 7.50 (t, 1H), 7.42 (t,
1H), 5.02 (s, 2H), 3.07 (s, 6H), 2.84–2.79 (m, 1H), 1.03–
0.99 (m, 2H), 0.86–0.81 (m, 2H). 13C-NMR: δ 167.86,
162.63, 152.99, 146.15, 135.56, 126.22, 125.41, 123.09,
121.77, 53.05, 38.92, 31.89, 7.65. HRMS (EI):
C15H18N6O4S3 (M)+ calcd. 442.0552; found 442.0555.
N3-Cyclopropyl-N1,N1-dimethyl-N3-(thiophen-3-ylmethyl)-
1H), 7.40–7.52 (m, 2H), 7.12–7.20 (m, 2H), 4.73 (s, 3H),
2.95 (s, 6H), 2.53–2.56 (m, 1H), 0.69–0.73 (m, 4H). 13C-
NMR: δ 169.98, 161.19, 151.87, 135.56, 126.32, 122.79,
53.05, 38.90, 31.91, 7.66. HRMS (EI): C15H19N7O4S2
(M)+ calcd. 425.0940; found 425.0941.
N3-Cyclopropyl-N1,N1-dimethyl-N3-(quinolin-2-ylmethyl)-
1H-1,2,4-triazole-1,3-disulfonamide (6j).
(65%). mp 123–125°C. H-NMR: δ (ppm) 8.63 (s, 1H),
White solid
1
1H-1,2,4-triazole-1,3-disulfonamide (6p).
White solid
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet