HCID 86697750, compound → 3-Amino-6-[1-(3-hydroxypropyl)-3-methyl-1H-pyrazol-4-yl]-N-methylpyridine-2-carboxamide

Participants

Reaction Steps

A mixture of 3-Amino-6-{1-[3-(benzyloxy)propyl]-3-methyl-1H-pyrazol-4-yl}-N-methylpyridine-2-carboxamide (Compound 34D, 639 mg, 1.68 mmol) in EtOH (18.0 mL) and palladium on carbon (10:90, Palladium 10% wt. on Calcium Carbonate:carbon black, 100.0 mg, 0.048 mmol) was evacuated and flushed with argon (3×). After a fourth evacuation, the mixture was flushed with H2 and allowed to stir overnight at rt. The reaction mixture was filtered, concentrated in vacuo and purified using a Teledyne ISCO Combiflash® Rf system [elution gradient: 0→10% MeOH in DCM] to afford 342 mg of the title compound (70%). 1H NMR (400 MHz, CDCl3) δ 8.01 (s, 1H), 7.42 (d, J=8.6 Hz, 1H), 7.16 (d, J=8.6 Hz, 1H), 4.19 (t, J=7.0 Hz, 2H), 3.55 (t, J=6.2 Hz, 2H), 2.94 (s, 3H), 2.48 (s, 3H), 2.05 (t, J=6.4 Hz, 2H). MS (ESI): m/z=290.58 [M+H]+. UPLC: tR=0.65 min (UPLC-SQD: analytical—2 min).

Provenance & Evidence