Methanamine, N-methoxy-, hydrochloride (1:1) → N-(1-(4-chlorophenyl)-3-(methoxy(methyl)carbamoyl)cyclobutyl)benzamide

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Reaction Steps

A solution of 3-benzamido-3-(4-chlorophenyl)cyclobutanecarboxylic acid (1.16 g, 3.52 mmol), diisopropylethylamine (1.57 mL, 9.14 mmol) and N,O-dimethylhydroxylamine hydrochloride (0.446 g, 4.572 mmol) in dichloromethane (45 mL) was treated with HATU (1.61 g, 4.22 mmol). After stirring overnight, the solution was diluted with dichloromethane (50 mL), washed successively with 1 M HCl (3×), 5% aqueous NaHCO3 and saturated aqueous sodium chloride. The organic phase dried over MgSO4, filtered and concentrated to give a colorless gum. Crystallization from diethyl ether gave the subject compound as a white crystalline solid (1.13 g 86%). 1H NMR (CDCl3, 600 MHz) δ 7.79 (d, J=7.5 Hz, 2H), 7.49-7.52 (m, 3H), 7.42-7.45 (m, 2H), 7.35 (d, J=8.5 Hz, 2H), 7.08 (bs, 1H), 3.68 (s, 3H), 3.43-3.47 (m, 1H), 3.22 (s, 3H), 2.98-3.01 (m, 2H), 2.87-2.91 (m, 2H). ESI MS found for C20H21ClN2O3 m/z [395.4/397.3 (M+NO, 373.3/375.3 (M+1), 371.3/373.3 (M−1)].

Provenance & Evidence