Imidazole → HCID 178483628, compound

HRID 967221Notes

Reaction equation

HRID 967221 reaction equation
[Cl:1][C:2]1[CH:28]=[CH:27][C:5]([O:6][C:7]([N:9]([CH3:26])[CH2:10][CH2:11][C@H:12]2[CH2:17][CH2:16][C@H:15]([CH2:18][CH2:19][CH2:20]OS(C)(=O)=O)[CH2:14][CH2:13]2)=[O:8])=[CH:4][CH:3]=1.[NH:29]1[CH:33]=[CH:32][N:31]=[CH:30]1.[H-].[Na+]>CN(C)C=O>[Cl:1][C:2]1[CH:28]=[CH:27][C:5]([O:6][C:7](=[O:8])[N:9]([CH2:10][CH2:11][C@H:12]2[CH2:17][CH2:16][C@H:15]([CH2:18][CH2:19][CH2:20][N:29]3[CH:33]=[CH:32][N:31]=[CH:30]3)[CH2:14][CH2:13]2)[CH3:26])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 24758Sodium hydrideHCID 178483635HCID 178483635, compound

Product 1

HCID 178483628HCID 178483628, compoundYield 55.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To an ice-cooled solution of 200 mg (0.46 mmol) trans-methanesulfonic acid 3-(4-{2-[(4-chloro-phenoxycarbonyl)-methyl-amino]-ethyl}-cyclohexyl)-propyl ester (example 11.16) and 126 mg (1.85 mmol) of imidazole in 3.5 ml of N,N-dimethylformamide was added at 0° C. 30.3 mg (0.69 mmol) of sodium hydride (55% in oil). The reaction mixture was then stirred for 4 hours at room temperature. After quenching with ammonium chloride solution, the reaction mixture was partitioned between water and ether. The combined ether phases were washed with brine, dried over magnesium sulfate and evaporated under reduced pressure. The residue formed was chromatographed on silica gel with a 95:5 v/v mixture of ethylacetate and methanol as the eluent giving 103 mg (55%) of pure trans-{2-[4-(3-imidazol-1-yl-propyl)-cyclohexyl]-ethyl}-methyl-carbamic acid 4-chloro-phenyl ester as colorless viscous oil, MS: 404 (MH+).

Workup

  1. additionwas added at 0° C
  2. customAfter quenching with ammonium chloride solution
  3. customthe reaction mixture was partitioned between water and ether
  4. washThe combined ether phases were washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated under reduced pressure
  7. customThe residue formed
  8. customwas chromatographed on silica gel with a 95:5 v/v mixture of ethylacetate and methanol as the eluent

Sources & evidence

ORD record
ord-ba3405453e534a35bc9d9f03c204d161
Source dataset
uspto-grants-2005_10
Patent number
US06953806B2

Reaction notes

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