Реакция #7276

ord-47eedb33bf164f6fbd23e37cca184a59

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
Nc1cc[nH]n1
3-aminopyrazole
CC(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+]
NaBH(OAc)3
c1cnc2c(c1)CCCC2N(Cc1ccc(CNc2cc[nH]n2)cc1)Cc1nc2ccccc2[nH]1
amine
Выход 23.0%
c1cnc2c(c1)CCCC2N(Cc1ccc(CNc2cc[nH]n2)cc1)Cc1nc2ccccc2[nH]1
(1H-Benzimidazol-2-ylmethyl)-{4-[(1H-pyrazol-3-ylamino)-methyl]-benzyl}-(5,6,7,8-tetrahydro-quinolin-8-yl)-amine
Выход 23.0%

Растворители

Условия реакции

Подробные условия
See reaction.notes.procedure_details.

Обработка

  1. 1
    ДругоеPurification of the crude material by radial chromatography on silica gel gel (2 mm plate, CH2Cl2/MeOH/NH4OH, 100:1:1

Методика

Using General Procedure B: To a stirred solution of 4-{[(1H-Benzimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzaldehyde (199 mg, 0.50 mmol) and 3-aminopyrazole (60 mg, 0.72 mmol) in THF (5 mL) and acetic acid (0.2 mL) was added NaBH(OAc)3 (166 mg, 0.78 mmol) and the resultant mixture stirred at room temperature for 2.5 days. Purification of the crude material by radial chromatography on silica gel gel (2 mm plate, CH2Cl2/MeOH/NH4OH, 100:1:1 then 50:1:1) afforded the desired amine (52 mg, 23%) as a white foam.

Источник

DOI: 10.6084/m9.figshare.5104873.v1Патент: US07084155B2uspto-grants-2006_08