Ammonium formate → HCID 178449205, compound

Participants

Reaction Conditions

Reaction Steps

N-(((3-(4-(Benzyloxy)-2-fluorophenyl)-1H-pyrazol-5-yl)amino)(isobutylamino)methylene)-1-methyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxamide (62 mg, 0.111 mmol) was dissolved in methanol (2 mL), and nitrogen gas was bubbled through briefly. 10% Palladium on carbon (59 mg, 0.5 equivalent) was then added, followed by ammonium formate (70 mg, 10 equivalents). The reaction vessel was sealed and then heated to 65° C. for 1 hour. Then, the crude mixture was cooled, and filtered through a plug of celite. The filtrate was concentrated onto silica gel and the crude product purified by chromatography (gradient: 9:1 hexanes:EtOAc to 1:1 hexanes:EtOAc) to provide the title compound as a white solid (17 mg, 33% yield). 1H NMR (DMSO-d6) δ 12.90 (s, 1H), 12.50 (s, 1H), 10.32 (bs, 1H), 8.83 (t, 1H), 8.28 (s, 1H), 7.55 (t, 1H), 6.65 (m, 2H), 6.35 (s, 1H), 3.89 (s, 3H), 3.39 (m, 2H), 1.83 (m, 1H), 0.94 (d, 6H). MS: calc.=467.42; obs. M+H=468.13. HPLC (Method E): retention time was 4.971 minutes.

Provenance & Evidence