Ammonium Chloride → HCID 178521905, compound

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Reaction Steps

A solution of 1-(3-chloro-benzenesulfonyl)-2,3-dihydro-1H-indole-6-carboxylic acid (4-cyano-3-trifluoromethyl-phenyl)-amide (30 mg, 0.06 mmol) in dimethylformamide (0.8 ml) was treated with sodium azide (71 mg, 1.1 mmol, 18 equiv.) and ammonium chloride (58 mg, 1.1 mmol, 18 equiv.). The solution was flushed with argon, then sealed and irradiated in microwave oven at 170° C. for 1 hour. The mixture was diluted with concentrated NaHCO3 and washed with ethyl acetate. The aqueous phase was acidified with HCl 1N to pH 1, then extracted twice with ethyl acetate. The combined organic phases were dried with Na2SO4 and the solvent evaporated to yield 15 mg (46% yield) of 1-(3-chloro-benzenesulfonyl)-2,3-dihydro-1H-indole-6-carboxylic acid [4-(1H-tetrazol-5-yl)-3-trifluoromethyl-phenyl]-amide as an orange foam, MS (ISP): m/e=547.2 (M−H), δH (300 MHz; d6-DMSO) 10.75 (1H, s), 8.41 (1H, s), 8.21 (1H, d), 7.97 (1H, s), 7.61-7.84 (5H, m), 7.56 (1H, t), 7.32 (1H, d), 3.98 (2H, t), 2.95 (2H, t).

Provenance & Evidence