Formaldehyde → HCID 118378898, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of (8-amino-6-(trifluoromethyl)imidazo[1,2-a]pyridin-3-yl)((1S,4S)-2-oxa-5-azabicyclo[2.2.1]hept-5-yl)methanone (207 mg) and oxalaldehyde (92.0 mg) in methanol (1.0 mL) was stirred at 70° C. for 5 hr. To the reaction mixture were added methanol (2.0 mL), ammonium chloride (67.9 mg) and formaldehyde (38.1 mg), and the mixture was heated with reflux for 30 min. Phosphoric acid (0.087 mL) was added thereto, and the mixture was heated with reflux overnight. Ice water and 8N aqueous sodium hydroxide solution were added to the reaction mixture at 0° C., and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane), and then HPLC (C18, mobile phase: water/acetonitrile (containing 0.1% TFA)). To the obtained fraction was added saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate, and concentrated under reduced pressure, and the obtained solid was recrystallized from ethyl acetate/hexane to give the title compound (12.6 mg).

Provenance & Evidence