反应 #7277

ord-d3399affb5e9484d901d531f62b141b6

反应方程式

c1ccc2c(c1)CCNC2
1,2,3,4-tetrahydroisoquinoline
O=Cc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1
4-{[(1H-benzimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzaldehyde
CC(=O)O
AcOH
CC(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+]
NaBH(OAc)3
c1ccc2c(c1)CCN(Cc1ccc(CN(Cc3nc4ccccc4[nH]3)C3CCCc4cccnc43)cc1)C2
foam
收率 78.4%
c1ccc2c(c1)CCN(Cc1ccc(CN(Cc3nc4ccccc4[nH]3)C3CCCc4cccnc43)cc1)C2
(1H-benzimidazol-2-ylmethyl)-[4-(3,4-dihydro-1H-isoquinolin-2-ylmethyl)-benzyl]-(5,6,7,8-tetrahydro-quinolin-8-yl)-amine
收率 78.4%

溶剂

反应条件

详细条件
See reaction.notes.procedure_details.

后处理

  1. 1
    其他Purification of the crude material by column chromatography on silica gel (500:5:1 CH2Cl2/MeOH/NH4OH)

实验过程

Using General Procedure B: To a stirred solution of 1,2,3,4-tetrahydroisoquinoline (49 mg, 0.37 mmol), 4-{[(1H-benzimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzaldehyde (140 mg, 0.34 mmol), and AcOH 0.020 mL, 0.35 mmol) in THF (3.5 mL) was added NaBH(OAc)3 (94 mg, 0.44 mmol) and the mixture was stirred at room temperature for 2 h. Purification of the crude material by column chromatography on silica gel (500:5:1 CH2Cl2/MeOH/NH4OH) afforded a colourless foam (137 mg).

来源

DOI: 10.6084/m9.figshare.5104873.v1专利: US07084155B2uspto-grants-2006_08