872728-81-9 → ethyl 3-(2-((4-(N-(hexyloxycarbonyl)carbamimidoyl)phenylamino)methyl)-1-methyl-N-(pyridin-2-yl)-1H-benzo[d]imidazole-5-carboxamido)propanoate

HRID 1852384Notes

Reaction equation

HRID 1852384 reaction equation
[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][O:7][C:8](/[N:10]=[C:11](/[NH2:46])\[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]([C:40]4[N:45]=[CH:44][CH:43]=[CH:42][CH:41]=4)[CH2:33][CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36])=[O:31])=[CH:29][C:22]=3[N:21]=2)=[CH:14][CH:13]=1)=[O:9].CS(O)(=O)=O>C(O)(C)C>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][O:7][C:8](/[N:10]=[C:11](\[NH2:46])/[C:12]1[CH:13]=[CH:14][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]([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:29][C:22]=3[N:21]=2)=[CH:16][CH:17]=1)=[O:9]

Participants

3

Reactant 1

HCID 10439877872728-81-9

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 1

HCID 3776IsopropanolSolvent

Procedure

26.5 kg of hydroxypropylcellulose are added to 720 kg of isopropanol in a 1200 L mixing container fitted with a propeller stirrer and the mixture is stirred until fully dissolved (about 12 to 60 hours; roughly 500 rpm). Once the solution is clear, 132.3 kg of dabigatran etexilate methanesulfonate (polymorph I) is added with stirring (400 rpm) and the mixture is stirred for about another 20 to 30 minutes. Then 21.15 kg of talc is added at a constant stirring rate and stirring is continued at the same speed for about another 10 to 15 minutes. The steps described above are preferably carried out under a nitrogen atmosphere.

Workup

  1. additionmixing container
  2. customfitted with a propeller stirrer
  3. dissolutionuntil fully dissolved (about 12 to 60 hours; roughly 500 rpm)
  4. stirringwith stirring (400 rpm)
  5. stirringthe mixture is stirred for about another 20 to 30 minutes
  6. stirringstirring
  7. customis continued at the same speed for about another 10 to 15 minutes

Sources & evidence

ORD record
ord-a6c91070685e4883ab107c8151211d76
Source dataset
uspto-grants-2015_02
Patent number
US08962574B2

Reaction notes

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