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, 229 μmol), azetidine-3-carboxylic acid (116 mg, 1147 μmol), and acetic acid (106 μL, 1836 μmol) in 1:1 CH2Cl2/MeOH (7.0 mL) was stirred at 25° C. for 1 h. Sodium cyanoborohydride (26 mg, 413 μmol) 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 2 mL DMSO+20 μL trifluoroacetic acid, filtered, and purified by rpHPLC (10-100% acetonitrile/water+0.1% TFA) to provide 1-((3-methyl-4-(5-(1-phenylcyclopropyl)-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). 1H NMR (400 MHz, MeOH) δ ppm 8.11 (d, J=8.6 Hz, 1 H), 7.88 (d, J=7.8 Hz, 1 H), 7.35-7.55 (m, 6 H), 7.27-7.34 (m, 1 H), 7.11 (d, J=8.6 Hz, 1 H), 4.47 (s, 2 H), 4.32-4.42 (m, 4 H), 3.63-3.81 (m, 1 H), 2.67 (s, 3 H), 1.70-1.77 (m, 2 H), 1.36-1.47 (m, 2 H)

Provenance & Evidence