N-(7-(2-chlorophenyl)-5-ethynyl-2,6-naphthyridin-3-yl)cyclopropanecarboxamide → N-(7-(2-chlorophenyl)-5-ethyl-2,6-naphthyridin-3-yl)cyclopropanecarboxamide
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:17]=[C:16]2[C:11]([CH:12]=[C:13]([NH:18][C:19]([CH:21]3[CH2:23][CH2:22]3)=[O:20])[N:14]=[CH:15]2)=[C:10]([C:24]#[CH:25])[N:9]=1>C(O)C.[Pt](=O)=O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:17]=[C:16]2[C:11]([CH:12]=[C:13]([NH:18][C:19]([CH:21]3[CH2:22][CH2:23]3)=[O:20])[N:14]=[CH:15]2)=[C:10]([CH2:24][CH3:25])[N:9]=1Participants
4
Procedure
N-(7-(2-chlorophenyl)-5-ethynyl-2,6-naphthyridin-3-yl)cyclopropanecarboxamide (40 mg, 0.1 mmol) was dissolved in ethanol (15 mL) and treated with platinum dioxide (3 mg, 0.01 mmol). The reaction flask was flushed with nitrogen and evacuated three times and then flushed with hydrogen gas, evacuated once, and then left under a balloon of hydrogen. The reaction mixture was stirred for 16 hours at room temperature and then filtered over a pad of Celite. The filtrate was evaporated in vacuo to afford a residue that was purified by reverse phase HPLC (5-85% acetonitrile in water with 0.1% ammonium hydroxide over 14 min) to afford the title compound as an off-white solid (20 mg, 50%). 1H NMR (400 MHz, DMSO) δ 11.16 (s, 1H), 9.31 (s, 1H), 8.78 (s, 1H), 8.08 (s, 1H), 7.77-7.69 (m, 1H), 7.61 (m, 1H), 7.54-7.42 (m, 2H), 3.24 (dd, J=15.2, 7.7 Hz, 2H), 2.15-2.07 (m, 1H), 1.38 (t, J=7.4 Hz, 3H), 0.95-0.80 (m, 4H). LCMS (Method E): RT=5.052 min, M+H+=352.1.