Acetic Acid → HCID 11590159, compound

Participants

Reaction Steps

A mixture of 6,8-difluoro-3,4-dihydro-1H-naphthalen-2-one (182 mg, 1 mmol), 2-amino-N-[5-(1,1-dimethyl-but-3-enyl)-[1,3,4]thiadiazol-2-yl]-butyramide HCl (305 mg, 1.0 mmol), NEt3 (0.14 ml), acetic acid (0.27 ml, 4 mmol), sodium sulfate in methylene chloride was stirred at room temperature for 1 hr. 95% pure sodium triacetoxy borohydride (424 mg, 2.0 mmol) was added and the mixture was stirred at rt overnight. The mixture was diluted with dilute water, saturated sodium bicarbonate to pH 7-7.5 and extracted with methylene chloride. The organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure. The crude products were purified by silica gel column chromatography using methylene chloride to 10% methanol in methylene chloride as eluent to give the title compound as ayellow oil. LC-MS, RT=2.1 min, M+1=435.3. The corresponding HCl salt was prepared as a beige solid.

Provenance & Evidence