4-Methylmorpholine → HCID 18923219, compound

Participants

Reaction Steps

Pivaloyl chloride (0.04 ml) was added dropwise to a mixture of tert-butoxycarbonyl-L-proline (77 mg), N-methylmorpholine (0.04 ml) and dichloromethane (3 ml) under a dry ice-tetrachloromethane bath cooling. This mixture was stirred for 5 minutes under an ice-water bath cooling and cooled under a dry ice-tetrachloromethane bath cooling. To the mixture was added a solution of 8-[3-(N-glycyl-N-methylamino)-2,6-dichlorobenzyloxy]-3-bromo-2-methylimidazo[1,2-a]pyridine (139 mg) in dichloromethane (4 ml). The mixture was stirred for 30 minutes at ambient temperature and washed with saturated aqueous solution of sodium hydrogen carbonate and water. The organic layer was dried over magnesium sulfate and evaporated in vacuo. The residue was purified by preparative thin-layer chromatography (dichloromethane:methanol=19:1, V/V) to give 3-bromo-8-[3-[N-(tert-butoxycarbonyl-L-prolylglycyl)-N-methylamino]-2,6-dichlorobenzyloxy]-2-methylimidazo[1,2-a]pyridine (72 mg) (Compound A), and 3-bromo-8-[2,6-dichloro-3-(N-methyl-N-pivaloylglycylamino)benzyloxy]-2-methylimidazo[1,2-a]pyridine (93 mg) (Compound B).

Provenance & Evidence