Potassium Carbonate → ethyl 3-(2-((4-(N-(hexyloxycarbonyl)carbamimidoyl)phenylamino)methyl)-1-methyl-N-(pyridin-2-yl)-1H-benzo[d]imidazole-5-carboxamido)propanoate

HRID 1470524Notes

Reaction equation

HRID 1470524 reaction equation
S(C1C=CC(C)=CC=1)(O)(=O)=O.[N:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[N:18]([CH2:42][CH2:43][C:44]([O:46][CH2:47][CH3:48])=[O:45])[C:19]([C:21]1[CH:41]=[CH:40][C:24]2[N:25]([CH3:39])[C:26]([CH2:28][NH:29][C:30]3[CH:35]=[CH:34][C:33]([C:36](=[NH:38])[NH2:37])=[CH:32][CH:31]=3)=[N:27][C:23]=2[CH:22]=1)=[O:20].Cl[C:50]([O:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH3:58])=[O:51].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.O>[CH3:58][CH2:57][CH2:56][CH2:55][CH2:54][CH2:53][O:52][C:50](/[N:38]=[C:36](\[NH2:37])/[C:33]1[CH:32]=[CH:31][C:30]([NH:29][CH2:28][C:26]2[N:25]([CH3:39])[C:24]3[CH:40]=[CH:41][C:21]([C:19]([N:18]([C:13]4[CH:14]=[CH:15][CH:16]=[CH:17][N:12]=4)[CH2:42][CH2:43][C:44]([O:46][CH2:47][CH3:48])=[O:45])=[O:20])=[CH:22][C:23]=3[N:27]=2)=[CH:35][CH:34]=1)=[O:51]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 22466Hexyl chloroformateHCID 16202315Dabigatran ethyl ester tosylate

Product 1

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

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

55 g of 1-methyl-2-[N-[4-amidinophenyl]aminomethyl]benzimidazol-5-yl carboxylic acid-N-(2-pyridyl)-N-(2-ethoxycarbonylethyl)amide tosylate was dissolved in 437 ml of acetone and 273 ml of water. 16.4 g of hexyl chloroformate and 34 g of potassium carbonate was added to it at a temperature of about 15° C. After the end of the reaction, the precipitated product is filtered off and washed with acetone/water. Dissolved the obtained solid in 270 ml of acetone under heating and then filtered. The title product was crystallized by the addition of 220 ml of water. The isolated substance is dried under reduced pressure at 45° C.

Workup

  1. customAfter the end of the reaction
  2. filtrationthe precipitated product is filtered off
  3. washwashed with acetone/water
  4. dissolutionDissolved the obtained solid in 270 ml of acetone
  5. temperatureunder heating
  6. filtrationfiltered
  7. customThe title product was crystallized by the addition of 220 ml of water
  8. customThe isolated substance is dried under reduced pressure at 45° C.

Sources & evidence

ORD record
ord-c51b1cda867140ca90bcb5001b84285c
Source dataset
uspto-grants-2015_04
Patent number
US09006448B2

Reaction notes

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