CJ-040714 → N-({1-[(4-Hydroxytetrahydro-2H-pyran-4-yl)methyl]piperidin-4-yl}methyl)-3-isopropyl-2-oxo-2,3-dihydro-1H-benzimidazole-1-carboxamide hydrochloride

HRID 502898Notes

Reaction equation

HRID 502898 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.[ClH:32].CO>CO>[ClH:32].[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

4

Reactant 2

HCID 11350913CJ-040714HCID 21893726Hydrochloride methanol

Product 1

HCID 68459910N-({1-[(4-Hydroxytetrahydro-2H-pyran-4-yl)methyl]piperidin-4-yl}methyl)-3-isopropyl-2-oxo-2,3-dihydro-1H-benzimidazole-1-carboxamide hydrochlorideYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of N-({1-[(4-hydroxytetrahydro-2H-pyran-4-yl)methyl]piperidin-4-yl}methyl)-3-isopropyl-2-oxo-2,3-dihydro-1H-benzimidazole-1-carboxamide (27.0 g, 62 mmol) in methanol (150 mL) was added 10% HCl-methanol (100 mL) at ambient temperature. After 30 min, the volatile materials were removed by evaporation. The resulting amorphous was precipitated by ethanol/diethylether. The precipitate was recrystallized from ethanol/diethylether (1:1) to give 26.5 g (90%) of title compound as a colorless powder.

Workup

  1. customthe volatile materials were removed by evaporation
  2. customThe resulting amorphous was precipitated by ethanol/diethylether
  3. customThe precipitate was recrystallized from ethanol/diethylether (1:1)

Sources & evidence

ORD record
ord-bca344ea65d54d10b2f0a28c5ec3cff6
Source dataset
uspto-grants-2010_08
Patent number
US07776885B2

Reaction notes

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