2-Amino-5-bromo-N-ethylbenzamide → 2-amino-N-ethyl-5-[1-(3-hydroxypropyl)-1H-pyrazol-4-yl]benzamide

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Reaction Steps

Prepared analogously to Compound 3C replacing Compound 3D with 2-amino-5-bromo-N-ethylbenzamide (Compound 9D, 1.40 g, 5.77 mmol) to afford 729 mg of the title compound (37%). 1H NMR (400 MHz, CD3OD) δ 7.87 (s, 1H), 7.76 (d, J=0.5 Hz, 1H), 7.63 (d, J=2.0 Hz, 1H), 7.34-7.41 (m, 1H), 6.77 (d, J=8.3 Hz, 1H), 4.25 (t, J=6.9 Hz, 2H), 3.54 (t, J=6.2 Hz, 2H), 3.38 (q, J=7.2 Hz, 2H), 2.06 (quin, J=6.6 Hz, 2H), 1.23 (t, J=7.2 Hz, 3H). MS (ESI): m/z 289.32 [M+H]+. UPLC: tR=0.63 min (UPLC-SQD: analytical—2 min).

Provenance & Evidence