Methanamine, N-methoxy-, hydrochloride (1:1) → 2-(1-isopropyl-3-methyl-1H-1,2,4-triazol-5-yl)-N-methoxy-N-methyl-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-9-carboxamide

Participants

Reaction Steps

To a solution of 2-(1-isopropyl-3-methyl-1H-1,2,4-triazol-5-yl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-9-carboxylic acid (4.00 g, 11.3 mmol) and N-methoxymethanamine hydrochloride (1.32 g, 13.6 mmol) in N,N-Dimethylformamide (100 mL) was added N-Ethyldiisopropylamine 7.9 mL, 45.3 mmol) followed by HBTU (4.72 g, 12.5 mmol). The reaction mixture was stirred at room temperature for 1 hour. LC-MS analysis of the reaction mixture showed no more starting material. The solvent was removed and the residue was diluted with DCM, washed with NaHCO3 sat. aq., dried over Na2SO4, filtered and concentrated. The resulting oil was purified on silica gel (0→10% MeOH/DCM) to give 2-(1-isopropyl-3-methyl-1H-1,2,4-triazol-5-yl)-N-methoxy-N-methyl-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-9-carboxamide

Provenance & Evidence