HRID250992

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID81531

Diisopropylethylamine

C8H19N

HCID15829159

tert-Butyl 2-(chloromethyl)-1H-benzimidazole-1-carboxylate

C13H15ClN2O2

HCID58997087

未命名化合物

PRODUCTS

生成物

结构：Cc1cccnc1CN(CCCCNC(=O)OC(C)(C)C)Cc1nc2ccccc2n1C(=O)OC(C)(C)C

HCID67272637

未命名化合物

收率 76%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID6342

Acetonitrile

C2H3N

PROCEDURE

实验过程

Using General Procedure A: A solution of {4-[(3-methyl-pyridin-2-ylmethyl)-amino]-butyl}-carbamic acid tert-butyl ester (0.605 g, 2.06 mmol), 1-(tert-butoxycarbonyl)-2-(chloromethyl)-benzimidazole (0.804 g, 3.01 mmol), KI (72 mg, 0.43 mmol) and DIPEA (0.70 mL, 4.02 mmol) in CH3CN (10 mL) was heated at 80° C. for 6 hours. Purification of the crude material by column chromatography on silica gel (15:1 CH2Cl2-MeOH) followed by column chromatography on silica gel (NH4OH saturated Et2O) provided 0.82 g (76%) of 2-{[(4-tert-Butoxycarbonylamino-butyl)-(3-methyl-pyridin-2-ylmethyl)-amino]-methyl}-benzoimidazole-1-carboxylic acid tert-butyl ester as a white foam.

WORKUP

后处理

customPurification of the crude material by column chromatography on silica gel (15:1 CH2Cl2-MeOH)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-2fcaccd175804fcdb56bd8a54afaa2c8
来源数据集: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
专利: US07863293B2
来源说明: uspto-grants-2011_01

反应 SMILES

[C:1]([O:5][C:6](=[O:21])[NH:7][CH2:8][CH2:9][CH2:10][CH2:11][NH:12][CH2:13][C:14]1[C:19]([CH3:20])=[CH:18][CH:17]=[CH:16][N:15]=1)([CH3:4])([CH3:3])[CH3:2].[C:22]([O:26][C:27]([N:29]1[C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=2[N:31]=[C:30]1[CH2:38]Cl)=[O:28])([CH3:25])([CH3:24])[CH3:23].CCN(C(C)C)C(C)C>CC#N>[C:22]([O:26][C:27]([N:29]1[C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=2[N:31]=[C:30]1[CH2:38][N:12]([CH2:11][CH2:10][CH2:9][CH2:8][NH:7][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:21])[CH2:13][C:14]1[C:19]([CH3:20])=[CH:18][CH:17]=[CH:16][N:15]=1)=[O:28])([CH3:25])([CH3:24])[CH3:23]