Ethylene Glycol → HCID 86689158, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of [bis-(4-methoxy-phenyl)-phenyl-methyl]-[(R)-4-(6-bromo-3-fluoro-pyridin-2-yl)-5,5-difluoro-4-methyl-5,6-dihydro-4H-[1,3]oxazin-2-yl]-amine (23.4 g, 28.8 mmol) in ammonia (173 ml, 1.21 mol, 7M in methanol) in a microwave vial was added ethylene glycol (240 ml) and methanol (240 ml). Copper oxide Cu2O (1.21 g, 8.46 mmol) was added and the vial was sealed. The reaction mixture was stirred at 80° C. for 43 hours. The cold reaction mixture was diluted with ethyl acetate and washed with water, aqueous ammonia and brine. The organic layer was dried over sodium sulfate, filtered and evaporated. The crude product was chromatographed over silica gel (400 g, dichloromethane/methanol 98:2+0.2% ammonia) to give the title compound: 4.29 g (25% yield).

Provenance & Evidence