1,2-Dichloroethane → 6-(4-(dimethylamino)piperidin-1-yl)-1-isopropyl-N-((6-methyl-2-oxo-4-propyl-1,2-dihydropyridin-3-yl)methyl)-1H-indazole-4-carboxamide

Participants

Reaction Steps

To a solution of 6-[4-(dimethylamino)-1-piperidinyl]-1-(1-methylethyl)-1H-indazole-4-carboxylic acid (34 mg, 0.103 mmol) in DMSO (1 mL) were added 3-(aminomethyl)-6-methyl-4-propyl-2(1H)-pyridinone (29.0 mg, 0.134 mmol), N-methylmorpholine (0.045 mL, 0.412 mmol), 1-hydroxy-7-azabenzotriazole (28.0 mg, 0.206 mmol) and EDC (39.5 mg, 0.206 mmol), and the mixture was stirred for 48 h. The mixture was purified using reverse-phase HPLC to afford the title compound as a pale yellow solid (34 mg). 1H NMR (400 MHz, DMSO-d6) δ ppm 0.77-0.96 (m, 3H), 1.43 (d, J=6.57 Hz, 6H), 1.46-1.66 (m, 4H), 1.89 (m, 2H), 2.13 (s, 3H), 2.31 (s, 6H), 2.33 (m, 2H), 2.55 (s, 3H), 2.65-2.84 (m, 2H), 3.86 (m, 2H), 4.38 (m, 2H), 4.85-5.04 (m, 1H), 5.91 (s, 1H), 7.07 (s, 1H), 7.32 (m, 1H), 8.15 (m, 1H), 8.25 (br. s., 1H), 8.44 (t, J=4.93 Hz, 1H); LCMS: (M+H)+=493.2

Provenance & Evidence