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

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Reaction Steps

Prepared analogously to Compound 3C replacing Compound 3D with 2-amino-5-bromo-N-methyl-benzamide (920 mg, 4.0 mmol) to give the title compound as 0.35 g of a white solid (32%, over two steps). 1H NMR (CDCl3+CD3OD, 400 MHz): δ=7.65 (s, 1H), 7.64 (s, 1H), 7.47 (d, J=2.0 Hz, 1H), 7.28 (dd, J=8.4, 2.0 Hz, 1H), 6.69 (d, J=8.4 Hz, 1H), 4.21 (t, J=6.6 Hz, 2H), 3.53 (t, J=5.6 Hz, 2H), 2.90 (s, 3H), 2.00 (m, 2H). MS (ESI): m/z=275.29 [M+H]+. HPLC: tR=2.50 min (ZQ3: polar—5 min).

Provenance & Evidence