4-cyano-1H-pyrrole-2-carboxylic acid → c-FMS inhibitor

Participants

Reaction Steps

The procedure of Example 53 was followed using 4-cyano-1H-pyrrole-2-carboxylic acid (as prepared in Example 2, 56 mg, 0.22 mmol) and 4-(4-methyl-piperazin-1-yl)-2-(4-methyl-piperidin-1-yl)-phenylamine (as prepared in Example 13, step (a), 61 mg 0.21 mmol). Purification of the resulting residue by silica gel preparative TLC eluting with 10% methanol in dichloromethane yielded 47 mg (55%) of the title compound as an off-white solid. 1H-NMR (400 MHz, CDCl3): δ 9.60 (br s, 1H), 8.30 (d, 1H, J=8.9), 7.24 (d, 1H, J=3.7 Hz), 7.21 (d, 1H, J=3.7 Hz), 6.79 (d, 1H, J=2.7 Hz), 6.73 (dd, 1H, J=8.9, 2.7 Hz), 3.20 (m, 4H), 3.00-2.97 (m, 2H), 2.76-2.70 (m, 2H), 2.59 (m, 4H), 2.37 (s, 3H), 1.85-1.82 (m, 2H), 1.56-1.46 (m, 2H), 1.07 (d, 3H, J=6.2 Hz). LC-MS (ESI, m/z): Calcd. for C23H31N6O, 407.3 (M+H); found: 407.2.

Provenance & Evidence