Propionic Acid → 2-(3-(2-methoxy-3H-imidazo[4,5-b]pyridin-3-yl)azetidin-1-yl)quinoline

Participants

Reaction Conditions

Reaction Steps

N2-(1-Quinolin-2-yl-azetidin-3-yl)-pyridine-2,3-diamine (150 mg, 0.51 mmol) was combined with tetramethylorthocarbonate (1 mL) and propionic acid (8 mg) and heated at 90° C. for 2 hours. After that, the reaction solution was concentrated under reduced pressure and the residue was purified by column chromatography on silica gel to give 2-(3-(2-methoxy-3H-imidazo[4,5-b]pyridin-3-yl)azetidin-1-yl)quinoline (100 mg, 0.30 mmol, 59% yield). M+1: 332. 1H NMR (CDCl3, 400 MHz): δ(ppm) 8.06-8.05 (m, 1 H); 7.87-7.85 (m, 1 H); 7.72-7.68 (m, 2 H); 7.58-7.47 (m, 2 H); 7.20-7.17 (m, 1 H); 7.06-7.03 (m, 1 H); 6.62-6.60 (m, 1 H); 5.62-5.55 (m, 1 H); 4.84-4.80 (m, 2 H); 4.61-4.57 (m, 2 H); 4.10 (s, 3 H).

Provenance & Evidence