Formaldehyde → N-[(3,4-dichlorophenyl)methyl]-4-hydroxy-N-methyl-5-oxo-1-[2-(1-piperidyl)ethyl]-2H-pyrrole-3-carboxamide

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Reaction Steps

3-[(3,4-Dichloro-benzyl-methyl-carbamoyl]-2-hydroxy-acrylic acid methyl ester (Compound 12-B) was treated with paraformaldehyde and 1-(2-aminoethyl)piperidine as described in the preparation of Compound 12. The resulting residue was purified by trituration with CH2Cl2 to yield the title compound as a white solid (81.2 mg, 38% yield). Decomposition point=178–182° C. 1H NMR (300 MHz, DMSO) δ: 10.99 (s, 1H), 7.62 (d, 1H, J=8.25), 7.52 (d, 1H, J=1.46), 7.26 (d, 1H, J=7.68), 4.60 (s, 2H), 4.13 (s, 2H), 3.81 (t, 2H, J=5.85), 3.48 (d, 2H, J=11.34), 3.27 (d, 2H. J=4.76), 3.00 (s, 2H), 2.86 (m, 3H), 1.77 (m, 6H). HRMS (M+H) calcd for C20H26N3Cl2O3: 426.1351. found: 426.1346.

Provenance & Evidence