1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 66721428, compound

Participants

Reaction Steps

To a solution of 7-({1-[(4-methoxybenzyl)(methyl)amino]pyridin-4-yl}oxy)-1,2,3,4-tetrahydronaphthalene-2-carboxylic acid (581 mg, 1.39 mmol) and 3-tert-butylaniline (228 mg, 1.53 mmol) in DCM (13 mL), was added DMAP (186 mg, 1.53 mmol) and EDCI (293 mg, 1.53 mmol). The reaction mixture was allowed to stir for 18 hr, and then diluted with EtOAc and washed with water and brine. The organic solution was dried over Na2SO4 and concentrated. The residue was purified by column to give N-(3-tert-butylphenyl)-7-({2-[(4-methoxybenzyl)(methyl)amino]pyridin-4-yl}oxy)-1,2,3,4-tetrahydronaphthalene-2-carboxamide (I-179) as a white solid (491 mg, 64.3%). 1H NMR (400 MHz, d6-DMSO; HCl salt) δ: 9.98 (s, 1H), 7.97 (d, 1H), 7.64 (dd, 1H), 7.49 (d, 1H), 7.21 (dd, 1H), 7.20 (d, 1H), 7.12 (d, 2H), 7.07 (ddd, 1H), 6.96 (d, 1H), 6.87-6.92 (m, 3H), 6.37-6.49 (m, 2H), 4.69 (s, 2H), 3.72 (s, 3H), 3.17 (s, 3H), 2.72-2.99 (m, 5H), 2.03-2.99 (m, 1H), 1.73-1.84 (m, 1H), and 1.26 (s, 9H). LCMS: (FA) ES+ 550.3, ES− 448.4.

Provenance & Evidence