Ethyl Acetate → HCID 178461311, compound

Participants

Reaction Steps

A mixture of 4-formylpyridine (0.88 g, 8.25 mmol), trans-4-methyl-cyclohexylamine hydrochloride (0.93 g, 8.25 mmol) and NaBH3CN (1.3 g, 20.6 mmol) in MeOH (50 mL) and AcOH (1.5 mL) was refluxed for 1.5 h. The heating was discontinued and the reaction mixture was left at rt for 2 days. The volatiles were removed in vacuo and the residue was divided between aqueous NaHCO3 and DCM. The DCM phase was concentrated in vacuo. Purification on preparative HPLC gave the TFA salt of (4-methyl-cyclohexyl)-pyridin-4-ylmethyl-amine. The amine was coupled and hydrolyses using the procedure described in the procedure for the preparation of 3-{2-[3-[2-(2-chloro-benzyloxy)-ethyl]-3-(trans-4-methyl-cyclohexyl)-ureido]-thiazol-5-ylsulfanyl}-2,2-dimethyl-propionic acid using 2-aminothiazol-5-ylsulfanyl)acetic acid ethyl ester

Provenance & Evidence