Sodium Hydroxide → HCID 89962654, compound

Participants

Reaction Steps

Ethyl 2-(6-(4-fluorophenyl)benzo[d]thiazol-2-yl)acetate (described in WO2011/074560, 500 mg, 1.59 mmol) in THF (4 mL) was treated with sodium hydroxide (1N NaOH, 1.9 mL, 1.9 mmol). After 2 hours, the reaction mixture was concentrated to dryness under reduced pressure. The residue was co-evaporated with toluene (5 mL), re-dissolved in DMF (4 mL), and treated with (5-methyl-1,3,4-oxadiazol-2-yl)methanamine hydrochloride (284 mg, 1.90 mmol), TEA (2.2 mL, 16 mmol) and PyBOP (990 mg, 1.9 mmol). After 16 hours, the reaction mixture was diluted with water (20 mL), extracted with DCM (3×10 mL), dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by silica gel (eluting with 0-20% DCM/MeOH) to give Compound A9a (485 mg, 80.0% yield) as an oil.

Provenance & Evidence