Methanesulfonic Acid → Dabigatran Etexilate Mesylate

HRID 1805896Notes

Reaction equation

HRID 1805896 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]([CH2:40][CH2:41][C:42]([O:44][CH2:45][CH3:46])=[O:43])[C:8]([C:10]1[CH:39]=[CH:38][C:13]2[N:14]([CH3:37])[C:15]([CH2:17][NH:18][C:19]3[CH:24]=[CH:23][C:22]([C:25](=[NH:36])[NH:26][C:27]([O:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])=[O:28])=[CH:21][CH:20]=3)=[N:16][C:12]=2[CH:11]=1)=[O:9].[CH3:47][S:48]([OH:51])(=[O:50])=[O:49]>CC(C)=O>[S:48]([OH:51])(=[O:50])(=[O:49])[CH3:47].[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]([CH2:40][CH2:41][C:42]([O:44][CH2:45][CH3:46])=[O:43])[C:8]([C:10]1[CH:39]=[CH:38][C:13]2[N:14]([CH3:37])[C:15]([CH2:17][NH:18][C:19]3[CH:20]=[CH:21][C:22]([C:25](=[NH:36])[NH:26][C:27]([O:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])=[O:28])=[CH:23][CH:24]=3)=[N:16][C:12]=2[CH:11]=1)=[O:9]

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 135565674Dabigatran Etexilate

Product 1

HCID 135566083Dabigatran Etexilate Mesylate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Conditions

Temperature
20 °C

Procedure

100 g (0.16 mol) of the compound (6B) are dissolved in 890 ml acetone with heating and combined with a solution of 15 g (0.16 mol) methanesulphonic acid in 200 ml acetone. The solution is filtered and after the addition of 77 ml acetone cooled to approx. 20° C. The precipitated product is isolated and washed with acetone.

Workup

  1. temperaturewith heating
  2. filtrationThe solution is filtered
  3. additionafter the addition of 77 ml acetone
  4. customThe precipitated product is isolated
  5. washwashed with acetone

Sources & evidence

ORD record
ord-1900d15b50ae4817a9c5a5697cc7d246
Source dataset
uspto-grants-2013_01
Patent number
US08354543B2

Reaction notes

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