HRID1527153

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID962

Water

H2O

HCID6395

Methanesulfonic acid

CH4O3S

$反应SMILES：CCCCCCOC(=O)/N=C(\N)c1ccc(NCc2nc3cc(C(=O)N(CCC(=O)OCC)c4ccccn4)ccc3n2C)cc1$

HCID6445226

未命名化合物

PRODUCTS

产物

反应SMILES：CCCCCCOC(=O)NC(=O)c1ccc(NCc2nc3cc(C(=O)N(CCC(=O)OCC)c4ccccn4)ccc3n2C)cc1

HCID70968095

未命名化合物

CONDITIONS

反应条件

温度: 50 °C

PROCEDURE

实验过程

32 g of dabigatran etexilate were suspended in 320 mL of deionized water. 5.4 g of methanesulfonic acid were added. The reaction mixture was heated to 50° C. and stirred at this temperature for 72 hours. The resulting mixture was filtered, and the solid was dried under vacuum. The solid was purified by column chromatography, eluting with ethyl acetate:methanol (15:1 v/v) mixture. After solvent evaporation of the selected fractions containing the desired compound, 15 g of ethyl 3-{[(2-{[(4-{[({hexyloxy}carbonyl)amino]carbonyl}-phenyl)amino]methyl}-1-methyl-1H-benzimidazol-5-yl)carbonyl](pyridin-2-yl)amino}propanoate 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 ethyl acetate:methanol (15:1 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-ea7f9fe5768543798c71ca9dd66d4ea6
来源数据集: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
专利号: US09086390B2
来源说明: uspto-grants-2015_07

反应SMILES

CCCCCC[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][CH2:38][CH3:39])=[O:36])=[O:31])=[CH:23][C:22]=3[N:21]=2)=[CH:16][CH:17]=1)=[O:9].CS(O)(=O)=O.[OH2:52]>>[CH2:14]([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:22]=[CH:23][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][CH2:38][CH3:39])=[O:36])=[O:31])=[CH:25][C:26]=3[N:21]=2)=[CH:16][CH:17]=1)=[O:52])=[O:9])[CH2:13][CH2:12][CH2:17][CH2:16][CH3:15]