Acetic Acid → 1-((3-Methyl-4-(5-(1-phenyl-cyclopropyl)thiazolo[5,4-b]pyridine-2-yl)phenyl)methyl)azetidine-3-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-methyl-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-yl)benzaldehyde (85.0 mg, 0.229 mmol), azetidine-3-carboxylic acid (116 mg, 1.147 mmol), and acetic acid (106 μL, 1.836 mmol) in 1:1 CH2Cl2/MeOH (7.0 mL) was stirred at 25° C. for 1 h. Sodium cyanoborohydride (26 mg, 0.413 mmol) was then added, and the resulting mixture was stirred at 25° C. for 16 h. The reaction mixture was then concentrated in vacuo, dissolved in DMSO (2 mL)+trifluoroacetic acid (20 μL), filtered, and purified by rpHPLC (10-100% acetonitrile/water+0.1% TFA) to provide 1-((3-methyl-4-(5-(1-phenyl-cyclopropyl)thiazolo[5,4-b]pyridine-2-yl)phenyl)methyl)azetidine-3-carboxylic acid as a white solid. MS (ESI) m/z: Calculated: 455.2; Observed: 456.1 (M++1).

Provenance & Evidence