Diisopropylethylamine → HCID 67496450, compound

Participants

Reaction Conditions

Reaction Steps

The (S)-2-amino-3-phenyl-1-(6-(pyrimidin-5-yl)indolin-1-yl)propan-1-one (39.0 mg, 110 μmol) was dissolved in a DCE/THF mixture 1.5 mL. Thiazole-4-carbaldehyde (13 mg, 110 μmol), diisopropylethyl amine (20 μl, 110 μmol), and sodium triacetoxyborohydride (48 mg, 230 μmol) was added to the reaction mixture. The resulting solution was heated to 70° C. and stirred for three hours. LCMS indicated starting material was still present. 24 mg of sodium cyanoborohydride was added and the solution was stirred at 70° C. overnight to completion. The reaction mixture was diluted with dichloromethane and basified with saturated sodium bicarbonate. The layers were separated and the organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The residue was then purified on an SCX column eluting with 0 to 2M ammonia in methanol solution to give impure product. This material was then purified by medium pressure chromatography (silica gel, 0 to 6.5% 2M ammonia in methanol: dichloromethane) to give the desired product (S)-3-phenyl-1-(6-(pyrimidin-5-yl)indolin-1-yl)-2-(thiazol-4-ylmethylamino)propan-1-one (16.6 mg, 33% yield). MS ESI (pos.) m/e: 442.1 (M+H).

Provenance & Evidence