1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → N-(-3-hydroxymethyl-4-{[(3-methyl-pyridin-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzyl)-2-phenyl-butyramide

Participants

Reaction Steps

Using General Procedure G: To a solution (S)-(5-aminomethyl-2-{[(3-methyl-pyridin-2-ylmethyl)-(1,2,3,4-tetrahydro-naphthalen-1-yl)amino]-methyl}-phenyl)-methanol (128 mg, 0.32 mmol) dissolved in CH2Cl2 (10 mL) was added (S)-2-phenylbutyric acid (74 μl, 0.48 mmol), EDCI (92 mg, 0.48 mmol), HOBT (65 mg, 0.48 mmol), and DIPEA (83 μl, 0.48 mmol). Purification via column chromatography on silica gel (CH2Cl2:MeOH, 97:3, v/v) afforded COMPOUND 439 as a colorless oil (37 mg, 22%). 1H NMR (CDCl3) δ 0.86 (m, 3H), 1.44 (m, 2H), 1.81 (m, 1H), 2.18 (m, 1H), 2.23 (s, 6H), 2.64 (m, 2H), 3.22 (m, 1H), 3.85 (m, 4H), 4.14 (m, 2H), 4.31 (m, 2H), 5.73 (m, 1H), 7.14 (m, 12H), 8.36 (m, 2H); ES-MS m/z 572 (M+H).

Provenance & Evidence