6-Chloro-N-(2-cyclopropylethyl)pyridazine-3-carboxamide → 6-[4-(3,3-Difluoro-2-oxo-2,3-dihydroindol-1-YL)piperidin-1-YL]pyridazine-3-carboxylic acid (2-cyclopropylethyl)amide

Participants

Reaction Steps

Following the procedure as described in Example 2, making variations only as required to use 6-chloropyridazine-3-carboxylic acid (2-cyclopropylethyl)amide to replace 6-chloropyridazine-3-carboxylic acid (3-cyclopropylpropyl)amide to react with 3,3-difluoro-1-piperidin-4-yl-1,3-dihydroindol-2-one, the title compound was obtained as a white powder in 77% yield (0.075 g). 1H NMR (300 MHz, CDCl3) δ 8.06 (m, 2H), 7.56-7.53 (m, 1H), 7.42 (t, J=9.0 Hz, 1H), 7.21-7.04 (m, 2H), 6.88 (d, J=6.9 Hz, 1H), 4.73-4.69 (m, 2H), 4.46-4.35 (m, 1H), 3.61-3.52 (m, 2H), 3.17-3.09 (m, 2H), 2.50-2.37 (m, 2H), 1.97-1.93 (m, 2H), 1.59-1.43 (m, 2H), 0.81-0.68 (m, 1H), 0.51-40 (m, 2H), 0.11-0.06 (m, 1H). 13C NMR (75 MHz, CDCl3) δ 165.2, 163.0, 159.6, 145.0, 142.4, 142.3, 133.5, 127.2, 125.2, 123.8, 120.4, 112.6, 110.8, 110.3, 50.9, 44.7, 39.7, 34.5, 27.6, 8.7, 4.2. MS (ES+) m/z 442.2 (M+1).

Provenance & Evidence