HRID1527152

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID6395

Methanesulfonic acid

CH4O3S

$结构：CCCCCCOC(=O)/N=C(\N)c1ccc(NCc2nc3cc(C(=O)N(CCC(=O)OCC)c4ccccn4)ccc3n2C)cc1.CS(=O)(=O)O$

HCID11434065

Dabigatran etexilate mesylate

C35H45N7O8S

PRODUCTS

生成物

结构：CCCCCCOC(=O)NC(=O)c1ccc(NCc2nc3cc(C(=O)N(CCC(=O)O)c4ccccn4)ccc3n2C)cc1

HCID70984799

未命名化合物

收率 28.4%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID962

Water

H2O

CONDITIONS

反应条件

温度: 55 °C

PROCEDURE

实验过程

25 g of dabigatran etexilate mesylate were suspended in 180 mL of deionized water. 1.32 g of methanesulfonic acid were added. The reaction mixture was heated to 55° C. and stirred at this temperature for 7 days. The resulting mixture was filtered, and the solid was dried under vacuum. The solid was purified by column chromatography, eluting with dichloromethane:methanol (10:1 v/v) mixture. After solvent evaporation of the selected fractions containing the desired compound, 5.9 g of 3-{[(2-{[(4-{[({hexyloxy}carbonyl)amino]carbonyl}phenyl)-amino]methyl}-1-methyl-1H-benzimidazol-5-yl)carbonyl](pyridin-2-yl)amino}propanoic acid were obtained.

WORKUP

后处理

filtrationThe resulting mixture was filtered
customthe solid was dried under vacuum
customThe solid was purified by column chromatography
washeluting with dichloromethane:methanol (10:1 v/v) mixture
customAfter solvent evaporation of the selected fractions
additioncontaining the desired compound

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-17f13e132678443794a9d8023eee1cba
来源数据集: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
专利: US09086390B2
来源说明: uspto-grants-2015_07

反应 SMILES

[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][O:7][C:8](/[N:10]=[C:11](\N)/[C:12]1[CH:13]=[CH:14][C:15]([NH:18][CH2:19][C:20]2[N:28]([CH3:29])[C:27]3[CH:26]=[CH:25][C:24]([C:30]([N:32]([C:40]4[CH:41]=[CH:42][CH:43]=[CH:44][N:45]=4)[CH2:33][CH2:34][C:35]([O:37]CC)=[O:36])=[O:31])=[CH:23][C:22]=3[N:21]=2)=[CH:16][CH:17]=1)=[O:9].CS(O)(=O)=[O:49].CS(O)(=O)=O>O>[CH2:6]([O:7][C:8]([NH:10][C:11]([C:12]1[CH:13]=[CH:14][C:15]([NH:18][CH2:19][C:20]2[N:28]([CH3:29])[C:27]3[CH:26]=[CH:25][C:24]([C:30]([N:32]([C:40]4[CH:41]=[CH:42][CH:43]=[CH:44][N:45]=4)[CH2:33][CH2:34][C:35]([OH:37])=[O:36])=[O:31])=[CH:23][C:22]=3[N:21]=2)=[CH:16][CH:17]=1)=[O:49])=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2][CH3:1]