4-bromo-1-(3-hydroxypropyl)-1H-pyrazole-3-carbonitrile → 3-amino-6-[3-cyano-1-(3-hydroxypropyl)-1H-pyrazol-4-yl]-N-methylpyridine-2-carboxamide

Participants

Reaction Steps

Prepared analogously to Compound 3C using 3-amino-N-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2-carboxamide (Compound 48D, 657 mg, 2.37 mmol) and 4-bromo-1-(3-hydroxypropyl)-1H-pyrazole-3-carbonitrile (Compound 52E, 600 mg, 2.61 mmol) to afford 164 mg of the title compound (23%). 1H NMR (400 MHz, CD3OD) δ 8.29 (s, 1H), 7.57 (d, J=8.6 Hz, 1H), 7.21 (d, J=8.6 Hz, 1H), 4.35 (t, J=6.8 Hz, 2H), 3.57 (t, J=6.1 Hz, 2H), 2.94 (s, 3H), 2.11 (t, J=6.1 Hz, 2H). MS (ESI): m/z=301.24 [M+H]+. UPLC: tR=0.79 min (UPLC-TOF: polar—2 min).

Provenance & Evidence