Potassium Carbonate → Dabigatran Ethyl Ester

HRID 1470517

Reaction equation

HRID 1470517 reaction equation
C(O)(=O)C(O)=O.[N:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N:13]([CH2:37][CH2:38][C:39]([O:41][CH2:42][CH3:43])=[O:40])[C:14]([C:16]1[CH:36]=[CH:35][C:19]2[N:20]([CH3:34])[C:21]([CH2:23][NH:24][C:25]3[CH:30]=[CH:29][C:28]([C:31](=[NH:33])[NH2:32])=[CH:27][CH:26]=3)=[N:22][C:18]=2[CH:17]=1)=[O:15].C(=O)([O-])[O-].[K+].[K+]>C(#N)C.O>[N:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N:13]([CH2:37][CH2:38][C:39]([O:41][CH2:42][CH3:43])=[O:40])[C:14]([C:16]1[CH:36]=[CH:35][C:19]2[N:20]([CH3:34])[C:21]([CH2:23][NH:24][C:25]3[CH:30]=[CH:29][C:28]([C:31](=[NH:32])[NH2:33])=[CH:27][CH:26]=3)=[N:22][C:18]=2[CH:17]=1)=[O:15]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 573893471-methyl-2[N-[4-amidinophenyl]aminomethyl]benzimidazol-5-yl-carboxylicacid-N-(2-pyridyl)-N-(2-ethoxycarbonylethyl)amide oxalate

Product 1

HCID 446804Dabigatran Ethyl Ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
12.5 °C

Procedure

Dissolved 1-methyl-2-[N-[4-amidinophenyl]aminomethyl]benzimidazol-5-yl-carboxylicacid-N-(2-pyridyl)-N-(2-ethoxycarbonylethyl)amide oxalate compound of formula-6a (100 g) in a mixture of acetonitrile (1200 ml) and water (800 ml) and cooled to 10-15° C. Potassium carbonate (66.24 g) was added to the reaction mixture and stirred for 60 minutes at 10-15° C. Filtered the obtained solid, washed with water and then dried to get title compound.

Workup

  1. filtrationFiltered the obtained solid
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-4de58e0a43bb4d5fbac88dc728973c97
Source dataset
uspto-grants-2015_04
Patent number
US09006448B2

Linked notes

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