6,8-Difluoro-2-tetralone → HCID 11676736, compound

Participants

Reaction Steps

A mixture of 6,8-difluoro-3,4-dihydro-1H-naphthalen-2-one (182 mg, 1 mmol), 2-amino-pentanoic acid [5-(1,1-dimethyl-butyl)-[1,3,4]thiadiazol-2-yl]-amide HCl (318 mg, 1.2 mmol), 95% pure sodium triacetoxy borohydride (335 mg, 1.5 mmol) in 7.0 mL of anhydrous dichloromethane and 2 ml of DMF was stirred at rt overnight. The reaction was not complete. The mixture was treated with NaBH3CN (140 mg) and stirred at room temperature for 15 hrs. All starting material and imine intermediate were consumed. The crude solution was diluted with dilute NaOH 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 to give the title compound. LC-MS, RT=2.2 min, M+1=449.0. The corresponding HCl salt was prepared as a beige solid.

Provenance & Evidence