Ethanol → HCID 178458589, compound

Participants

Reaction Steps

3-Chloro-N2-[(1S)-1-(5-fluoropyridin-2-yl)ethyl]-N6-(5-isopropoxy-1H-pyrazol-3-yl)-5-nitropyridine-2,6-diamine (Intermediate 39, 0.5 g) was dissolved into ethanol (20 mL) with Pd—C (150 mg) and a hydrogen inlet. The mixture was stirred at room temperature until no starting material was detected with TLC or LCMS. Formylamidine acetate (0.5 g) was added to the filtrate after the filtration of resulting mixture. The mixture was stirred at 85° 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 0.12 g desired product. MS (electrospray): 416 (M+1) for C19H19ClFN7O. 1H NMR (300 MHz, CD3OD) δ ppm 8.40 (s, 1H) 8.30 (s, 1H) 7.90 (d, 1H) 7.50 (m 2H) 6.70 (d, 1H) 6.00 (s, 1H) 5.40 (m, 1H) 4.60 (m, 1H) 1.60 (d, 3H) 1.40 (d, 6H).

Provenance & Evidence