Methanol → HCID 71257642, compound

Participants

Reaction Steps

In a 250 mL round-bottomed flask, 2-(6-tert-butyl-8-fluoro-1-oxophthalazin-2(1H)-yl)-4-(1-methyl-5-(5-(1-methylpiperidin-4-yl)pyridin-2-ylamino)-6-oxo-1,6-dihydropyridazin-3-yl)nicotinaldehyde (1.62 g, 2.6 mmol, Eq: 1.00) was combined with dry CH2Cl2 (45 ml) and dry MeOH (20 mL) to give a brown solution. Sodium borohydride (177 mg, 4.68 mmol, Eq: 1.8) was added and the reaction was stirred at ambient temperature for 1 h before being quenched with sat'd NH4Cl. The reaction mixture was diluted with 50 mL H2O and extracted with CH2Cl2 (3×150 mL). The organic layers were dried over Na2SO4 and concentrated in vacuo. The crude material was purified by flash chromatography [silica gel, 80 g, 0% to 50% (60:10:1 CH2Cl2:MeOH: NH40H) in CH2Cl2] to afford a slightly impure foam. The foam was slurried in ml Et2O and 10 ml EtOAc and stirred slowly with a heavy stir bar for 1 h resulting in a white solid. The solid was collected by filtration, dried under vacuum at 50° C. for 48 h. to afford the desired product as a white solid (880 mg). (M+H)+=625 m/e. 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 1.44 (s, 9 H) 1.87 (br. s., 3 H) 2.15 (br. s., 2 H) 2.39 (br. s., 3 H) 2.52 (t, J=7.74 Hz, 1 H) 3.04 (br. s., 2 H) 3.82-3.91 (m, 1 H) 3.93 (s, 3 H) 4.46-4.63 (m, 2 H) 6.93 (d, J=8.69 Hz, 1 H) 7.42-7.59 (m, 3 H) 7.64 (d, J=4.91 Hz, 1 H) 8.15-8.39 (m, 3 H) 8.70 (s, 1 H) 8.73 (d, J=4.91 Hz, 1 H)

Provenance & Evidence