Acetyl chloride → 3-Amino-4-thiophen-2-yl-6,7-dihydro-5H-1-thia-6,8-diaza-s-indacene-2-carboxylic acid amide hydrochloride

Participants

Reaction Steps

To a suspension of 3-amino-2-carbamoyl-4-thiophen-2-yl-5,7-dihydro-1-thia-6,8-diaza-s-indacene-6-carboxylic acid tert-butyl ester (4 g, 9.6 mmol)) in 70 ml of anhydrous methanol was added dropwise 7 ml of acetyl chloride under argon. The resulting mixture was stirred for 48 hours at room temperature. The solid was filtered and washed with methanol to give 3.14 g (93%) of the yellow product as its hydrochloride salt. 1H-NMR (300 MHz, DMSO-d6): δ 10.20 (brs, 2H), 7.96 (dd, J=1.2, 5.1 Hz, 1H), 7.36 (dd, J=1.2, 3.6 Hz, 1H), 7.32 (brs, 2H), 7.31 (dd, J=3.6, 5.1 Hz, 1H), 6.02 (brs, 2H), 4.63 (s, 2H), 4.42 (s, 2H). ES MS m/z 317 (M+H)+, 315 (M−H)−.

Provenance & Evidence