Methanesulfonic Acid → ethyl 3-[[2-[[4-[(Z)-N'-hexoxycarbonylcarbamimidoyl]anilino]methyl]-1-methylbenzimidazole-5-carbonyl]-pyridin-2-ylamino]propanoate;methanesulfonic acid

HRID 919286Notes

Reaction equation

HRID 919286 reaction equation
[CH3:1][S:2]([OH:5])(=[O:4])=[O:3].[CH3:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13](/[N:15]=[C:16](\[NH2:51])/[C:17]1[CH:18]=[CH:19][C:20]([NH:23][CH2:24][C:25]2[N:33]([CH3:34])[C:32]3[CH:31]=[CH:30][C:29]([C:35]([N:37]([C:45]4[CH:46]=[CH:47][CH:48]=[CH:49][N:50]=4)[CH2:38][CH2:39][C:40]([O:42][CH2:43][CH3:44])=[O:41])=[O:36])=[CH:28][C:27]=3[N:26]=2)=[CH:21][CH:22]=1)=[O:14]>O1CCCC1>[CH3:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13](/[N:15]=[C:16](\[NH2:51])/[C:17]1[CH:18]=[CH:19][C:20]([NH:23][CH2:24][C:25]2[N:33]([CH3:34])[C:32]3[CH:31]=[CH:30][C:29]([C:35]([N:37]([C:45]4[CH:46]=[CH:47][CH:48]=[CH:49][N:50]=4)[CH2:38][CH2:39][C:40]([O:42][CH2:43][CH3:44])=[O:41])=[O:36])=[CH:28][C:27]=3[N:26]=2)=[CH:21][CH:22]=1)=[O:14].[CH3:1][S:2]([OH:5])(=[O:4])=[O:3]

Participants

4

Reactant 2

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

Product 1

HCID 11434065ethyl 3-[[2-[[4-[(Z)-N'-hexoxycarbonylcarbamimidoyl]anilino]methyl]-1-methylbenzimidazole-5-carbonyl]-pyridin-2-ylamino]propanoate;methanesulfonic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methane sulfonic acid (1.5 g) was slowly added to a mixture of Dabigatran etexilate (10 g) and tetrahydrofuran (120 ml) at 25-30° C. and stirred for 5 hours. Filtered the precipitated solid, washed with tetrahydrofuran and then dried to get crystalline form-I of Dabigatran etexilate mesylate.

Workup

  1. filtrationFiltered the precipitated solid
  2. washwashed with tetrahydrofuran
  3. customdried

Sources & evidence

ORD record
ord-5c81bf0b8ccd42d1a1cbbc4ca5e87f70
Source dataset
uspto-grants-2016_03
Patent number
US09273030B2

Reaction notes

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