Water → HCID 25115858, compound

HRID 218047Notes

Reaction equation

HRID 218047 reaction equation
[CH3:1][C:2]1[NH:6][C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[N:3]=1.[C:11]([NH:16][C:17]1[CH:18]=[C:19]([CH:23]2[CH2:28][CH2:27][N:26]([CH2:29][CH2:30][CH2:31]CS([O-])(=O)=O)[CH2:25][CH2:24]2)[CH:20]=[CH:21][CH:22]=1)(=[O:15])[CH:12]([CH3:14])[CH3:13].C([O-])([O-])=O.[K+].[K+].O>CN(C)C=O>[CH3:1][C:2]1[N:6]([CH2:31][CH2:30][CH2:29][N:26]2[CH2:27][CH2:28][CH:23]([C:19]3[CH:20]=[CH:21][CH:22]=[C:17]([NH:16][C:11](=[O:15])[CH:12]([CH3:14])[CH3:13])[CH:18]=3)[CH2:24][CH2:25]2)[C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 119842-MethylbenzimidazoleHCID 86761577HCID 86761577, compound

Product 1

HCID 25115858HCID 25115858, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

100 mg (0.75 mmol) of 2-methyl-1H-benzimidazole was dissolved in 5 ml of N,N-dimethylformamide, and 286 mg (0.75 mmol) of 3-[4-(3-isobutyrylaminophenyl)piperidin-1-yl]propylmethanesulfonate and 310 mg (2.25 mmol) of K2CO3 were added to the resulting solution, followed by treating the mixture at 80° C. for 5 hours. The reaction mixture was combined with 50 ml of water and extracted with ethylacetate (50 ml×2) being washed with water and a sodium hydroxide solution, and then the combined organic layer was dried over anhydrous sodium sulfate, and filtered. The solvent was removed from the filtrate under a reduced pressure, and the resulting residue was refined by silica gel column chromatography (5% MeOH/CH2Cl2) to obtain 159 mg (yield 51%) of the title compound.

Workup

  1. additionby treating the mixture at 80° C. for 5 hours
  2. extractionextracted with ethylacetate (50 ml×2)
  3. washbeing washed with water
  4. dry with materiala sodium hydroxide solution, and then the combined organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customThe solvent was removed from the filtrate under a reduced pressure

Sources & evidence

ORD record
ord-d8b4da76ffd6425792f0abcc48145e63
Source dataset
uspto-grants-2012_06
Patent number
US08198307B2

Reaction notes

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