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Ammonia → Dabigatran ethyl ester mesylate

HRID 919287
Notes
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Reaction equation

HRID 919287 reaction equation
Cl.[Cl-].[Ca+2].[Cl-].[S:5]([OH:9])(=[O:8])(=[O:7])[CH3:6].[C:10]([C:12]1[CH:17]=[CH:16][C:15]([NH:18][CH2:19][C:20]2[N:24]([CH3:25])[C:23]3[CH:26]=[CH:27][C:28]([C:30]([N:32]([CH2:39][CH2:40][C:41]([O:43][CH2:44][CH3:45])=[O:42])[C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][N:34]=4)=[O:31])=[CH:29][C:22]=3[N:21]=2)=[CH:14][CH:13]=1)#[N:11].C(=O)([O-])[O-].[NH4+:50].[NH4+].N>C(O)C>[S:5]([OH:9])(=[O:8])(=[O:7])[CH3:6].[C:10]([C:12]1[CH:17]=[CH:16][C:15]([NH:18][CH2:19][C:20]2[N:24]([CH3:25])[C:23]3[CH:26]=[CH:27][C:28]([C:30]([N:32]([CH2:39][CH2:40][C:41]([O:43][CH2:44][CH3:45])=[O:42])[C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][N:34]=4)=[O:31])=[CH:29][C:22]=3[N:21]=2)=[CH:14][CH:13]=1)(=[NH:50])[NH2:11]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 5

HCID 222AmmoniaHCID 313Hydrochloric Acid2×HCID 517111Ammonium CarbonateHCID 5284359Calcium ChlorideHCID 72192623Ethyl 3-(2-((4-cyanophenylamino)methyl)-1-methyl-N-(pyridin-2-yl)-1H-benzo[d]imidazole-5-carboxamido)propanoate mesylate

Product 1

HCID 72192622
Dabigatran ethyl ester mesylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
-10 °C

Procedure

Hydrogen chloride gas was passed into a mixture of calcium chloride (125 g) and ethanol (1500 ml) at a temperature below 20° C. for a period of 30 minutes. The reaction mixture was cooled to −15 to −5° C. and stirred for 15 minutes. Ethyl 3-(2-((4-cyanophenylamino)methyl)-1-methyl-N-(pyridin-2-yl)-1H-benzo[d]imidazole-5-carboxamido)propanoate mesylate compound of formula-10 (500 g) was added to the reaction mixture. Hydrogen chloride gas was slowly purged into the reaction mixture for a period of 3 hours. The temperature of the reaction mixture was raised to 25-35° C. and stirred for 10 hours. After completion of the reaction, expell the hydrogen chloride gas present in the reaction mixture under nitrogen atmosphere. Ethanol (2500 ml), followed by ammonium carbonate (2000 g) were added to the reaction mixture and stirred for 40 minutes at −30±5° C. The reaction mixture was cooled to 0-5° C. and ammonia gas was passed into the reaction mixture for 3 hours. The temperature of the reaction mixture was raised to 20-30° C. and stirred for 20 hours. After completion of the reaction, filtered the reaction mixture and the filtrate was concentrated to get title compound. Purity by HPLC: 80.61%;

Workup

  1. customHydrogen chloride gas was slowly purged into the reaction mixture for a period of 3 hours
  2. temperatureThe temperature of the reaction mixture was raised to 25-35° C.
  3. stirringstirred for 10 hours
  4. customAfter completion of the reaction
  5. additionwere added to the reaction mixture
  6. stirringstirred for 40 minutes at −30±5° C
  7. temperatureThe reaction mixture was cooled to 0-5° C.
  8. temperatureThe temperature of the reaction mixture was raised to 20-30° C.
  9. stirringstirred for 20 hours
  10. customAfter completion of the reaction
  11. filtrationfiltered the reaction mixture
  12. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-1c4800e50e6c422aa829cbf38f46af4f
Source dataset
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09273030B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes