Imidazole → HCID 17808988, compound

HRID 1597318Notes

Reaction equation

HRID 1597318 reaction equation
N1[CH:5]=[CH:4][N:3]=[CH:2]1.C[Si](Cl)(C)C.[NH2:11][C:12]1[C:33]([Cl:34])=[CH:32][C:15]([C:16]([NH:18][CH:19]2[CH2:24][CH2:23][N:22]([CH2:25][CH:26]3CCN[CH2:28][CH2:27]3)[CH2:21][CH2:20]2)=[O:17])=[C:14]([O:35][CH3:36])[CH:13]=1.[OH2:37]>CN(C)C=O>[NH2:11][C:12]1[C:33]([Cl:34])=[CH:32][C:15]([C:16]([NH:18][CH:19]2[CH2:24][CH2:23][N:22]([CH2:25][CH:26]3[CH2:5][CH2:4][N:3]([CH:2]=[O:37])[CH2:28][CH2:27]3)[CH2:21][CH2:20]2)=[O:17])=[C:14]([O:35][CH3:36])[CH:13]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 6397ChlorotrimethylsilaneHCID 10937790HCID 10937790, compound

Product 1

HCID 17808988HCID 17808988, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of imidazole (330 mg) in dimethylformamide (0.74 ml) is added trimethylsilyl chloride (0.61 ml) at room temperature, and the mixture is stirred for 20 minutes. To the solution is added 4-amino-5-chloro-2-methoxy-N-[1-(4-piperidinylmethyl)-4-piperidinyl]-benzamide (610 mg), and the mixture is stirred at room temperature for 24 hours. To the reaction mixture is added a small amount of water, and the mixture is concentrated to dryness under reduced pressure. To the residue is added water, and the mixture is extracted with chloroform. The organic layer is washed with a saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and the solvent is evaporated under reduced pressure. The residue is purified by silica gel column chromatography (eluent; chloroform:methanol=30:1→20:1) to give the desired compound (200 mg) as amorphous.

Workup

  1. stirringthe mixture is stirred at room temperature for 24 hours
  2. concentrationthe mixture is concentrated to dryness under reduced pressure
  3. additionTo the residue is added water
  4. extractionthe mixture is extracted with chloroform
  5. washThe organic layer is washed with a saturated aqueous sodium chloride solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. customthe solvent is evaporated under reduced pressure
  8. customThe residue is purified by silica gel column chromatography (eluent; chloroform:methanol=30:1→20:1)

Sources & evidence

ORD record
ord-e64970c93b1d44b9ba6cf37decc7c9de
Source dataset
uspto-grants-2001_09
Patent number
US06294555B1

Reaction notes

Loading…