Ethylenediamine → HCID 23585426, compound

Participants

Reaction Steps

A solution of 4-{[7-({[3-[2-(1,3-dihydro-2H-isoindol-2-yl)ethyl]-5-(trifluoromethyl)phenyl]amino}carbonyl)-5,6,7,8-tetrahydronaphthalen-2-yl]oxy}-N-methylpyridine-2-carboxamide (0.158 g, 0.25 mmol) and ethane-1,2-diamine (2 mL) was allowed to stir at rt overnight. The reaction mixture was diluted with EtOAc and water. The solution was extracted with EtOAc. The combined organic solutions were washed with brine and concentrated to give a white solid. The residue was purified by column chromatography to give 4-{[7-({[3-(2-aminoethyl)-5-(trifluoromethyl)phenyl]-amino}carbonyl)-5,6,7,8-tetrahydronaphthalen-2-yl]oxy}-N-methylpyridine-2-carboxamide (I-47, 137 mg, 29%) as the formate salt. 1H NMR (300 MHz, CD3OD): δ 8.44 (d, 1H), 8.42 (s, 1H), 7.91 (s, 1H), 7.78 (s, 1H), 7.51 (s, 1H), 7.34 (s, 1H), 7.24-7.21 (m, 1H), 7.07-7.04 (m, 1H), 6.92-6.89 (m, 1H), 3.24-3.19 (m, 2H), 3.10-2.78 (m, 9H), 2.56-2.13 (m, 1H), and 2.03-1.84 (m, 2H).

Provenance & Evidence