4-bromo-1-(3-hydroxypropyl)-1H-pyrazole-5-carbonitrile → 3-amino-6-[5-cyano-1-(3-hydroxypropyl)-1H-pyrazol-4-yl]-N-methylpyridine-2-carboxamide

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Reaction Steps

Prepared analogously to 3C using 3-amino-N-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2-carboxamide (Compound 48D, 475.3 mg, 1.715 mmol) and 4-bromo-1-(3-hydroxypropyl)-1H-pyrazole-5-carbonitrile (Compound 52D, 434 mg, 1.89 mmol) to afford 151 mg of the title compound (29%). 1H NMR (400 MHz, CD3OD) δ 8.08 (s, 1H), 7.63 (d, J=8.6 Hz, 1H), 7.21 (d, J=8.8 Hz, 1H), 4.47 (t, J=7.1 Hz, 2H), 3.60 (t, J=6.1 Hz, 2H), 2.94 (s, 3H), 2.15 (quin, J=6.6 Hz, 2H). MS (ESI): m/z=301.24 [M+H]+. UPLC: tR=0.79 min (UPLC-TOF: polar—2 min).

Provenance & Evidence