Isopropanol → HCID 46241608, compound

Participants

Reaction Conditions

Reaction Steps

NaH (95%, 51 mg, 2 mmol) was added into IPA (4 mL) at 0° C. slowly until bubble disappeared. To this solution was added N-({1-[4-(6-fluoro-pyridin-3-yl)-4-hydroxy-cyclohexyl]-azetidin-3-ylcarbamoyl}-methyl)-3-trifluoromethyl-benzamide (6a, 200 mg, 0.40 mmol) in DMF (1 mL). After addition, the reaction was heated for another 2 hours at 80° C. The reaction solution was quenched with MeOH and partitioned between DCM and water. The organic layer was separated and the aqueous layer was extracted 3 times with chloroform and IPA “cocktail” (˜3:1, v/v). The combined organic layer was dried over anhydrous Na2SO4, filtered and concentrated to give the crude product, which was then purified by a CombiFlash® system using ethyl acetate and 7N NH3 in MeOH as eluent (from pure ethyl acetate to 5% 7N NH3 in MeOH in ethyl acetate) to afford the title compound as a white solid.

Provenance & Evidence