Acetic Acid → 1-((2,6-Dimethyl-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-yl)phenyl)methyl)-azetidine-3-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

A mixture of 2,6-dimethyl-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-yl)benzaldehyde (22.4 mg, 0.058 mmol), azetidine-3-carboxylic acid (29.5 mg, 0.29 mmol), and acetic acid (26.9 μl, 0.466 mmol) in 1:1 CH2Cl2/MeOH (2.0 mL) was stirred at 25° C. for 1 h. Sodium cyanoborohydride (6.59 mg, 0.105 mmol) was then added, and the resulting mixture was stirred at 25° C. for 15 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-((2,6-dimethyl-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-yl)phenyl)methyl)azetidine-3-carboxylic acid as a light yellow solid. MS (ESI) m/z: Calculated: 469.2; Observed: 470.1 (M++1). (2,6-

Provenance & Evidence