Ethanol → 3-(5-Cyclopropyl-1H-pyrazol-3-yl)-N-[(1S)-1-(5-fluoropyridin-2-yl)ethyl]-3H-imidazo[4,5-b]pyridin-5-amine

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Reaction Steps

N2-(5-cyclopropyl-1H-pyrazol-3-yl)-N6-[(1S)-1-(5-fluoropyridin-2-yl)ethyl]-3-nitropyridine-2,6-diamine (Intermediate 10, 0.4 g) was dissolved into ethanol (20 mL) with Pd—C (60 mg) and a hydrogen inlet. The mixture was stirred at room temperature until no starting material was detected with TLC or LCMS. Formamidine acetate (0.5 g) was added to the filtrate after the filtration of resulting mixture. The mixture was stirred at 95° C. for 4 hours. Ethyl acetate (40 mL) was added into the resulting mixture, and brine (10 mL×3) was used to wash the organic layer. The organic layer was dried and concentrated. The resulting residue was separated by silica gel column (Ethyl acetate/MeOH) to afford 0.16 g of the title compound. MS (electrospray): 364 (M+1) for C19H18FN7. 1H NMR (300 MHz, CD3OD) δ ppm 8.45 (s, 1H) 8.30 (s, 1H) 7.70 (d, 1H) 7.50 (d, 1H) 6.70 (d, 1H) 6.20 (s, 1H) 5.10 (dd, 1H) 2.00 (m, 1H) 1.55 (d, 3H) 1.00 (m, 2H) 0.80 (m, 2H).

Provenance & Evidence