Acetyl chloride → HCID 59618662, compound

Participants

Reaction Steps

To a solution of 6-[(4-tert-butylphenyl)sulfonyl]-2-(trifluoromethyl)-6,11-dihydro-5H-pyrido[2,3-b][1,5]benzodiazepine-8-carbohydrazide (intermediate 57, 0.040 g, 0.0771 mmol) and triethylamine (0.038 mL) in THF (0.65 mL) at rt was added acetyl chloride (8.5 mg, 0.108 mmol), and the reaction was stirred at rt overnight. The volatiles were removed and the residue was chromatographed on a SiO2 column to provide acetyl product, which was mixed with POCl3 (60 mg, 0.4 mmol) and acetonitrile (0.14 mL), and was stirred at 80° C. for 3 h. The volatiles were removed, and the residue was purified by SiO2 column chromatography to provide the title compound. LC/MS: m/e 544.1 (M+H)+. 1H NMR (500 MHz, CDCl3): δ 8.21 (1H, d, J=1.9 Hz), 8.02 (1H, dd, J=8.5, 2.1 Hz), 7.63 (1H, d, J=7.5 Hz), 7.15 (1H, d, J=7.6 Hz), 7.13 (1H, d, J=8.7 Hz), 7.04 (1H, br s), 6.96 (2H, J=8.5 Hz), 6.90 (1H, d, J=8.6 Hz), 4.65-4.95 (2H, br), 2.67 (3H, s), 1.26 (9H, s).

Provenance & Evidence