Реакция #9030

ord-fc9e474d8b844c12ad0aa6bd3324f2d5

Уравнение реакции

O=Cc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1
4-{[(1H-Benzimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzaldehyde
CNC
dimethylamine
CC(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+]
NaBH(OAc)3
CN(C)Cc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1
title compound
Выход 43.0%
CN(C)Cc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1
(1H-Benzimidazol-2-ylmethyl)-(4-dimethylaminomethyl-benzyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amine
Выход 43.0%

Растворители

Условия реакции

Подробные условия
See reaction.notes.procedure_details.

Обработка

  1. 1
    Другоеfollowed by purification of the crude material by radial chromatography on silica gel (2 mm plate, 50:1:1 CH2Cl2—CH3OH—NH4OH)

Методика

Using General Procedure B: Reaction of 4-{[(1H-Benzimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzaldehyde (AMD9882) (157 mg, 0.40 mmol) and dimethylamine (2.0 M in THF, 0.4 mL, 0.80 mmol) with NaBH(OAc)3 (0.179 g, 0.84 mmol) in CH2Cl2 (4 mL) overnight followed by purification of the crude material by radial chromatography on silica gel (2 mm plate, 50:1:1 CH2Cl2—CH3OH—NH4OH) provided the free base of the title compound (72 mg, 43%) as a colorless oil.

Источник

DOI: 10.6084/m9.figshare.5104873.v1Патент: US07091217B2uspto-grants-2006_08