Benzyloxyamine hydrochloride → HCID 19101709, compound

Participants

Reaction Conditions

Reaction Steps

4-(Benzylamino)-1-cyclopropyl-5,7-difluoro-6-(4-methyl-1-piperazinyl)-2-benzimidazoleacetamide (4.4 g, 9.7 mmol) and O-benzyl-hydroxylamine hydrochloride (6.2 g, 38.8 mmol) are suspended in water-ethanol (1:1; 100 ml) and warmed to 60° C. for two days. After cooling, the pH is adjusted to 5-6 with saturated aqueous sodium bicarbonate solution and the resulting solution extracted with ethyl acetate. The combined organic layers are dried (magnesium sulfate), concentrated and chromatographed on silica gel (eluent: 5% then 15% methanol-dichloromethane), affording 2.6 g of 2-[7-benzylamino-1-cyclopropyl-4.6-difluoro-5-(4-methyl-piperazin-1-yl)-1H-benzimidazol-2-yl]-N-benzyloxy-acetamide (48%): NMR (CDCl3): 1.04 (m,4H),2.42(s,3H),2.65 (m,4H), 3.27 (m,5H), 3.93(s,2H),4.67(s,2H),4.89(s,2H),7.20-7.39(m,10H), 10.47(s,1H).

Provenance & Evidence