Morpholine → HCID 178496439, compound

Participants

Reaction Steps

To a solution under Ar of (RS)-3-[(4-cyano-benzylcarbamoyl)-methoxy-methyl]-2,4-difluoro-benzoic acid (150 mg) in DMF (2 ml) was added 1,1′-carbonyldiimidazole (74 mg). The reaction mixture was stirred 15 min at rt before addition of morpholine. After stirring 2 h at rt hydroxylamine hydrochloride (289 mg) and Et3N (0.3 ml) were added. The reaction mixture was stirred 20 h at rt, then it was poured on H2O (20 ml) and extracted with AcOEt (2×20 ml). The organic layers were washed with brine and dried (Na2SO4) and the solvent was evaporated. CC (AcOEt/MeOH 99:1 to 9:1) yielded 111 mg (58%) of (RS)-2-[2,6-difluoro-3-(morpholine-4-carbonyl)-phenyl]-N-[4-(N-hydroxycarbamimidoyl)-benzyl]-2-methoxy-acetamide. White solid. MS 463.5 ([M+H]+).

Provenance & Evidence