3-(Aminomethyl)-4,6-dimethyl-1,2-dihydropyridin-2-one → 6-chloro-1-cyclopentyl-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1H-indazole-4-carboxamide

Participants

Reaction Steps

The title compound was prepared in the same manner as described for example 3 (step c) from 6-chloro-1-cyclopentyl-1H-indazole-4-carboxylic acid (0.12 g, 0.453 mmol) and 3-(aminomethyl)-4,6-dimethyl-2(1H)-pyridinone (0.128 g, 0.680 mmol), wherein the stir time was 12 h. The crude product was purified by silica gel chromatography (eluent: 5-85% gradient chloroform (containing 10% 2M Ammonia in methanol) and dichloromethane). The isolated product was concentrated from MTBE to afford an off-white solid that was dried in hi-vac oven for 6 h. The final product was collected as 0.165 g (89%); 1H NMR (400 MHz, DMSO-d6) δ ppm 1.62-1.74 (m, 2H) 1.81-1.91 (m, 2H) 1.91-2.02 (m, 2H) 2.06-2.17 (m, 5H) 2.20 (s, 3H) 4.34 (d, J=4.80 Hz, 2H) 5.16-5.28 (m, 1H) 5.88 (s, 1H) 7.60 (d, J=1.52 Hz, 1H) 8.05 (s, 1H) 8.37 (s, 1H) 8.61 (t, J=4.93 Hz, 1H) 11.54 (s, 1H); LC-MS (ES) m/z=398.8 [M+H]+

Provenance & Evidence