Reacción #7274

ord-9059553ff0014d51a2fe1da9bed22a25

Ecuación de reacción

O=Cc1ccccn1
Pyridine-2-carbaldehyde
CC(NCc1cccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)c1)c1ccccc1
(1H-Benzimidazol-2-ylmethyl)-{3-[(1-phenyl-ethylamino)-methyl]-benzyl}-(5,6,7,8-tetrahydro-quinolin-8-yl)-amine
CC(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+]
sodium triacetoxyborohydride
CC(c1ccccc1)N(Cc1cccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)c1)Cc1ccccn1
title compound
Rendimiento 50.0%
CC(c1ccccc1)N(Cc1cccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)c1)Cc1ccccn1
(1H-Benzimidazol-2-ylmethyl)-(3-{[(1-phenyl-ethyl)-pyridin-2-ylmethyl-amino]-methyl}-benzyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amine
Rendimiento 50.0%

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Otrofollowed by purification of the crude material by chromatography on silica gel (2:2:96 CH3OH—NH3 H2O—CH2Cl2)

Procedimiento

Using general procedure B: Reaction of Pyridine-2-carbaldehyde (22 mg, 0.20 mmol, (1H-Benzimidazol-2-ylmethyl)-{3-[(1-phenyl-ethylamino)-methyl]-benzyl}-(5,6,7,8-tetrahydro-quinolin-8-yl)-amine (101 mg, 0.20 mmol) and sodium triacetoxyborohydride (58 mg, 0.26 mmol) in CH2Cl2 (2 mL) at room temperature under N2 for 20 h, followed by purification of the crude material by chromatography on silica gel (2:2:96 CH3OH—NH3 H2O—CH2Cl2) afforded the title compound (60 mg, 50%) as a white foam.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US07084155B2uspto-grants-2006_08