Acetic Acid → HCID 59149834, compound

Participants

Reaction Conditions

Reaction Steps

Sodium cyanotrihydroborate (58.5 mg, 0.93 mmol) was added to a stirred mixture of 6-(6,6-difluoro-1,4-diazepan-1-yl)-3-(trifluoromethyl)[1,2,4]triazolo[4,3-b]pyridazine (200 mg, 0.62 mmol), 4-fluorobenzaldehyde (93 mg, 0.75 mmol) and acetic acid (71.1 μl, 1.24 mmol) in methanol (10 mL) at room temperature. The resulting mixture was stirred at 21° C. for 20 hours. The reaction mixture was concentrated to dryness, diluted with methanol and a few drops of 7M ammonia in methanol were added. The mixture was concentrated to dryness, the residue was diluted with DCM and the salts were filtered off. The filtrate was concentrated and purified by flash chromatography on silica gel eluting with 0 to 20% acetonitrile in DCM. Product-containing fractions were concentrated to give to give 6-[6,6-difluoro-4-(4-fluorobenzyl)-1,4-diazepan-1-yl]-3-(trifluoromethyl)[1,2,4]triazolo[4,3-b]pyridazine (154 mg, 55%).

Provenance & Evidence