Dimethylformamide → HCID 178451392, compound

HRID 534894Notes

Reaction equation

HRID 534894 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[CH2:16][CH2:15][N:14]([C:17]([C:19]2[CH:28]=[CH:27][C:22]3[NH:23][C:24]([SH:26])=[N:25][C:21]=3[CH:20]=2)=[O:18])[CH2:13][CH2:12]1)([CH3:4])([CH3:3])[CH3:2].Br[CH2:30][C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[CH2:16][CH2:15][N:14]([C:17]([C:19]2[CH:28]=[CH:27][C:22]3[NH:23][C:24]([S:26][CH2:30][C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])=[N:25][C:21]=3[CH:20]=2)=[O:18])[CH2:13][CH2:12]1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 178440807HCID 178440807, compound

Product 1

HCID 178451392HCID 178451392, compoundYield 81.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 5-{[4-(2-tert-butylphenyl)piperazin-1-yl]carbonyl}-1H-benzimidazole-2-thiol obtained in Example 27 (750 mg), tert-butyl bromoacetate (429 mg), potassium carbonate (415 mg), and N,N-dimethylformamide (5 mL) was stirred at room temperature for 16 h. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by flash column chromatography (silica gel, 90:10-50:50 hexane/ethyl acetate) to provide the title compound (785 mg, 81%) as an amorphous.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by flash column chromatography (silica gel, 90:10-50:50 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-e97df80ac5794634add948ba7c803e55
Source dataset
uspto-grants-2014_10
Patent number
US08853215B2

Reaction notes

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