Sodium borohydride → HCID 58798986, compound

Participants

Reaction Conditions

Reaction Steps

To N1-(3-fluoro-4-(5-((4-oxocyclohexylidene)methyl)pyrrolo[2,1-f][1,2,4]triazin-4-yloxy)phenyl)-N3-(4-fluorophenyl)malonamide (80 mg, 0.15 mmol, Example 149) in methanol (2 mL) at 0° C. was added a spatula tip of sodium borohydride. The reaction was stirred at 0° C. for 30 min and was then quenched with saturated aqueous ammonium chloride solution (10 mL) and stirred at 0° C. for 5 min. The mixture was extracted with ethyl acetate (3×10 mL) and the combined organic extracts were dried over anhydrous sodium sulfate and concentrated in vacuo. The crude product was purified by flash chromatography on silica gel (10% MeOH/EtOAc) to give the title compound (30 mg, 37%) as an off-white solid. 1H NMR (DMSO-d6) δ 10.57 (s, 1H), 10.34 (s, 1H), 8.11 (d, 1H, J=2.8 Hz), 8.10 (s, 1H), 7.86 (dd, 1H, J=12.8, 2.4 Hz), 7.71-7.68 (m, 2H), 7.53 (t, 1H, J=8.4 Hz), 7.46-7.43 (m, 1H), 7.25-7.21 (m, 2H), 6.99 (d, 1H, J=2.8 Hz), 6.64 (s, 1H), 4.65 (br s, 1H), 3.76-3.75 (m, 1H), 3.56 (s, 2H), 2.90-2.85 (m, 1H), 2.51-2.45 (m, 1H), 2.27-2.24 (m, 2H), 1.92-1.85 (m, 2H), 1.46-1.41 (m, 2H); MS(ESI+) m/z 534.3 (M+H)+.

Provenance & Evidence