CJ-040714 → CJ-040714 hemi-edisylate salt

HRID 502901Notes

Reaction equation

HRID 502901 reaction equation
[OH:1][C:2]1([CH2:8][N:9]2[CH2:14][CH2:13][CH:12]([CH2:15][NH:16][C:17]([N:19]3[C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=4[N:21]([CH:28]([CH3:30])[CH3:29])[C:20]3=[O:31])=[O:18])[CH2:11][CH2:10]2)[CH2:7][CH2:6][O:5][CH2:4][CH2:3]1.O.O.[CH2:34]([S:40]([OH:43])(=[O:42])=[O:41])[CH2:35][S:36]([OH:39])(=[O:38])=[O:37]>C(OCC)(=O)C.CO>[S:36]([CH2:35][CH2:34][S:40]([OH:43])(=[O:42])=[O:41])([OH:39])(=[O:38])=[O:37].[OH:1][C:2]1([CH2:8][N:9]2[CH2:10][CH2:11][CH:12]([CH2:15][NH:16][C:17]([N:19]3[C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=4[N:21]([CH:28]([CH3:29])[CH3:30])[C:20]3=[O:31])=[O:18])[CH2:13][CH2:14]2)[CH2:7][CH2:6][O:5][CH2:4][CH2:3]1.[OH:1][C:2]1([CH2:8][N:9]2[CH2:10][CH2:11][CH:12]([CH2:15][NH:16][C:17]([N:19]3[C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=4[N:21]([CH:28]([CH3:29])[CH3:30])[C:20]3=[O:31])=[O:18])[CH2:13][CH2:14]2)[CH2:7][CH2:6][O:5][CH2:4][CH2:3]1

Participants

5

Reactant 2

HCID 11350913CJ-040714HCID 57346009Ethane-1,2-disulfonic acid--water (1/2)

Product 1

HCID 71587808CJ-040714 hemi-edisylate saltYield 61.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent3×HCID 8857Ethyl AcetateSolvent2×

Procedure

To a stirred solution of N-({1-[(4-hydroxytetrahydro-2H-pyran-4-yl)methy]piperidin-4-yl}methyl)-3-isopropyl-2-oxo-2,3-dihydro-1H-benzimidazole-1-carboxamide 1.51 g (3.51 mmol) in ethyl acetate (10 mL) and methanol (10 mL) was added a solution of 1,2-ethanedisulfonic acid dihydrate 397 mg (1.75 mmol) in methanol (5.0 mL) and the resulting suspension was stirred for 5 h at room temperatute. The mixture was filtered and the first crop was dried under vacuum for 5 h at 100° C. to give 1.78 g of crude product. 1.61 g of the crude product was dissolved in methanol (20 mL) and ethyl acetate (20 mL) was added to the solution. The resulting suspension was stirred for 2 h at room temperatute. The mixture was filtered and the crop was dried under vacuum for 4 h at 100° C. to give the titled compound 1.13 g (61%) as colorless crystals.

Workup

  1. filtrationThe mixture was filtered
  2. customthe first crop was dried under vacuum for 5 h at 100° C.
  3. customto give 1.78 g of crude product
  4. stirringThe resulting suspension was stirred for 2 h at room temperatute
  5. filtrationThe mixture was filtered
  6. customthe crop was dried under vacuum for 4 h at 100° C.

Sources & evidence

ORD record
ord-dc308bc166fe465cb7c72e0a74bff0e6
Source dataset
uspto-grants-2010_08
Patent number
US07776885B2

Reaction notes

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