Triethylamine → HCID 178490720, compound

Participants

Reaction Steps

A solution of hydroxylamine hydrochloride (223 mg, 3.21 mmol, 5 equiv.) in dimethyl sulfoxide (3 ml) was treated with triethylamine (0.45 ml, 3.21 mmol, 5 equiv.) and stirred at room temperature for 5 min. The white precipitate was filtered off and to the filtrate, 1-(5-chloro-2-methoxy-benzenesulfonyl)-2,3-dihydro-1H-indole-6-carboxylic acid (4-cyano-phenyl)-amide (300 mg, 0.64 mmol, 1 equiv.) (prepared as illustrated in example 37, steps 1 to 3) was added. The mixture was stirred at 75° C. for 1 hour and 15 min. The reaction mixture was then cooled to room temperature, diluted with water and extracted with ethyl acetate. The organic phase was extracted three times with 0.5 N HCl. The combined aqueous phase was adjusted to pH 9-10 with NaOH 1N and extracted three times with ethyl acetate. The combined organic phases were dried with Na2SO4 and the solvent was evaporated. Crude 1-(5-chloro-2-methoxy-benzenesulfonyl)-2,3-dihydro-1H-indole-6-carboxylic acid [4-(N-hydroxycarbamimidoyl)-phenyl]-amide was obtained as a white solid, 261 mg (81%), which was used as such in the following reaction. MS (ISP): m/e=501.3 (M+H+.), δH (300 MHz; d6-DMSO) 10.25 (1H, s), 9.50 (1H, s), 7.80 (1H, s), 7.55-7.71 (7H, m), 7.28 (1H, d), 7.16 (1H, d), 5.69 (2H, s), 4.04 (2H, t), 3.60 (3H, s), 3.06 (2H, t).

Provenance & Evidence