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Water → Ethyl 3-(2-(((4-(((hexyloxy)carbonyl)carbamoyl)phenyl)amino)methyl)-1-methyl-N-(pyridin-2-yl)-1H-benzimidazole-5-carboxamido)propanoate

HRID 1527153
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HRID 1527153 반응식
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]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

4

반응물 3

HCID 962WaterHCID 6395Methanesulfonic AcidHCID 6445226ethyl 3-(2-((4-(N-(hexyloxycarbonyl)carbamimidoyl)phenylamino)methyl)-1-methyl-N-(pyridin-2-yl)-1H-benzo[d]imidazole-5-carboxamido)propanoate

생성물 1

HCID 70968095Ethyl 3-(2-(((4-(((hexyloxy)carbonyl)carbamoyl)phenyl)amino)methyl)-1-methyl-N-(pyridin-2-yl)-1H-benzimidazole-5-carboxamido)propanoate

반응 조건

온도
50 °C

실험 절차

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.

후처리

  1. filtrationThe resulting mixture was filtered
  2. customthe solid was dried under vacuum
  3. customThe solid was purified by column chromatography
  4. washeluting with ethyl acetate:methanol (15:1 v/v) mixture
  5. customAfter solvent evaporation of the selected fractions
  6. additioncontaining the desired compound

출처 및 근거

ORD 기록
ord-ea7f9fe5768543798c71ca9dd66d4ea6
출처 데이터셋
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09086390B2

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