Ethyl isocyanate → HCID 58902434, compound

Participants

Reaction Steps

To a solution of 4-{[7-({[3-(aminomethyl)-5-(trifluoromethyl)phenyl]amino}-carbonyl)-5,6,7,8-tetrahydronaphthalen-2-yl]oxy}-N-methylpyridine-2-carboxamide (0.411 g, 0.824 mmol) and TEA (0.23 mL, 1.65 mmol) in THF (10 mL) was added isocyanatoethane (0.10 mL, 1.26 mmol) in THF (5 mL) dropwise. The reaction mixture was allowed to stir at rt overnight. The reaction mixture was diluted with water and extracted with DCM. The organic solutions were combined, washed with brine, dried over MgSO4, filtered, and concentrated. The residue was purified by column chromatography and then converted to the HCl salt of 4-{[7-({[3-({[(ethylamino)carbonyl]amino}methyl)-5-(trifluoromethyl)phenyl]amino}carbonyl)-5,6,7,8-tetrahydronaphthalen-2-yl]oxy}-N-methylpyridine-2-carboxamide I-420. 1H NMR (400 MHz, d6-DMSO; HCl salt) δ: 10.42 (s, 1H), 8.84 (dd, 1H), 0.51 (dd, 1H), 8.03 (s, 1H), 7.68 (s, 1H), 7.41 (dd, 1H), 7.22-7.26 (m, 2H), 7.17 (dd, 1H), 7.01 (dd, 1H), 7.96 (dd, 1H), 4.23 (s, 2H), 3.01 (dd, 2H), 2.94 (dd, 2H), 2.80-2.90 (m, 3H), 2.77 (dd, 3H), 2.08-2.14 (m, 1H), 1.75-1.86 (m, 1H), and 0.98 (dd, 3H). LCMS: (FA) ES+ 570.7, ES− 568.4.

Provenance & Evidence