Water → HCID 58902453, compound

Participants

Reaction Steps

To a solution of 4-{[7-({[3-({[(1,3dioxo-1,3-dihydro-2-H-isoindol-2-yl)acetyl]-amino}methyl)-5-(trifluoromethyl)phenyl]amino}carbonyl)-5,6,7,8-tetrahydronaphthalen-2-yl]-oxy}-N-methylpyridine-2-carboxamide (0.819 g, 1.19 mmol) in EtOH (20 mL) was added a 40% aqueous solution of methyl amine in water (5.00 mL, 44.8 mmol). The reaction mixture was allowed to stir at rt for 5 h and then concentrated. The residue was purified by column chromatography to give N-methyl-4-{[7-({[3-({[(methylamino)acetyl]amino}-methyl)-5-(trifluoromethyl)phenylamino}carbonyl)-5,6,7,8-tetrahydronaphthalen-2-yl]oxy}-pyridine-2-carboxamide I-345 (0.124 g, 19%) as a white solid. 1H NMR (400 MHz, d6-DMSO, HCI salt) δ: 10.65 (s, 1H), 9.19-9.09 (br s, 1H), 8.85-8.77 (m, 1H), 8.50 (d, 1H), 8.17-8.02 (m, 2H), 7.66 (s, 1H), 7.41-7.36 (m, 1H), 7.28-7.21 (m, 1H), 7.19-7.14 (m, 1H), 7.04-6.94 (m, 2H), 4.22 (t, 2H), 3.83-3.76 (m, 2H), 3.67 (t, 2H), 3.03-2.81 (m, 5H), 2.77 (d, 3H), 2.17-2.08 (m, 1H), and 1.89-1.75 (m, 1H). LCMS: (FA) ES+543.2, ES−541.2.

Provenance & Evidence