Methanesulfonic Acid → 1-(4-methoxybutyl)-N-(2-methylpropyl)-N-[(3S,5R)-5-(morpholin-4-ylcarbonyl)piperidin-3-yl]-1H-benzimidazole-2-carboxamide methanesulfonate

HRID 1260109Notes

Reaction equation

HRID 1260109 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][CH2:6][N:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[N:9]=[C:8]1[C:16]([N:18]([CH2:33][CH:34]([CH3:36])[CH3:35])[C@H:19]1[CH2:24][C@@H:23]([C:25]([N:27]2[CH2:32][CH2:31][O:30][CH2:29][CH2:28]2)=[O:26])[CH2:22][NH:21][CH2:20]1)=[O:17].[CH3:37][S:38]([OH:41])(=[O:40])=[O:39].CCCCCC>C(OCC)(=O)C>[CH3:37][S:38]([OH:41])(=[O:40])=[O:39].[CH3:1][O:2][CH2:3][CH2:4][CH2:5][CH2:6][N:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[N:9]=[C:8]1[C:16]([N:18]([CH2:33][CH:34]([CH3:36])[CH3:35])[C@H:19]1[CH2:24][C@@H:23]([C:25]([N:27]2[CH2:32][CH2:31][O:30][CH2:29][CH2:28]2)=[O:26])[CH2:22][NH:21][CH2:20]1)=[O:17]

Participants

5

Reactant 3

HCID 6395Methanesulfonic AcidHCID 8058HexaneHCID 44554894Imarikiren

Product 1

HCID 866422161-(4-methoxybutyl)-N-(2-methylpropyl)-N-[(3S,5R)-5-(morpholin-4-ylcarbonyl)piperidin-3-yl]-1H-benzimidazole-2-carboxamide methanesulfonate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

1-(4-Methoxybutyl)-N-(2-methylpropyl)-N-[(3S,5R)-5-(morpholin-4-ylcarbonyl)piperidin-3-yl]-1H-benzimidazole-2-carboxamide (208 mg) was dissolved in ethyl acetate (2 ml), a solution of methanesulfonic acid (40 μl) in ethyl acetate (1 ml) was added at 75° C., hexane (1 ml) was added, and the mixture was heated under reflux and stood at room temperature overnight. The precipitated crystals were collected by filtration, and dried at 70° C. for 3 hr to give the object product (158 mg).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux
  3. filtrationThe precipitated crystals were collected by filtration
  4. customdried at 70° C. for 3 hr

Sources & evidence

ORD record
ord-b09cf91fea75422c90dfcdd2ac30b871
Source dataset
uspto-grants-2013_06
Patent number
US08466282B2

Reaction notes

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