2-amino-N,N-diethyl-5-[1-(3-hydroxypropyl)-1H-pyrazol-4-yl]benzamide → 6-amino-2-fluoro-3-[1-(3-hydroxypropyl)-1H-pyrazol-4-yl]-N-methylbenzamide

Participants

Reaction Steps

Prepared analogously to Compound 3C replacing Compound 3D with 6-amino-3-bromo-2-fluoro-N-methylbenzamide (Compound 27D, 700 mg, 2.83 mmol) to afford 281 mg of the title compound (34%). 1H NMR (400 MHz, CD3OD) δ=7.88 (d, J=1.8 Hz, 1H), 7.76 (d, J=1.0 Hz, 1H), 7.38 (t, J=8.6 Hz, 1H), 6.59 (d, J=8.6 Hz, 1H), 4.26 (t, J=7.0 Hz, 2H), 3.54 (t, J=6.2 Hz, 2H), 2.92 (s, 3H), 1.98-2.13 (m, 2H). MS (ESI): m/z=293.87 [M+H]+. UPLC: tR=0.60 min (UPLC-SQD: analytical—2 min).

Provenance & Evidence