Potassium Carbonate → HCID 57786041, compound

HRID 1399016Notes

Reaction equation

HRID 1399016 reaction equation
[C:1]([O:4][CH2:5][CH:6](O)[CH2:7][N:8]1[C:12]2[C:13]([N:17]([CH2:20][CH3:21])[CH2:18][CH3:19])=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[NH:22][C:23]1[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][C:24]=1[Cl:30])(=[O:3])[CH3:2].CS(Cl)(=O)=O.C(=O)([O-])[O-].[K+].[K+]>N1C=CC=CC=1.CN(C)C=O.C(OCC)(=O)C>[C:1]([O:4][CH2:5][CH:6]1[CH2:7][N:8]2[C:9](=[N:10][C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([N:17]([CH2:18][CH3:19])[CH2:20][CH3:21])[C:12]=32)[N:22]1[C:23]1[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][C:24]=1[Cl:30])(=[O:3])[CH3:2]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 31297Methanesulfonyl chlorideHCID 68773737HCID 68773737, compound

Product 1

HCID 57786041HCID 57786041, compoundYield 98%

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 3-[2-[(2,4-dichlorophenyl)amino]-7-(diethylamino)-1H-benzimidazol-1-yl]-2-hydroxypropyl acetate (Reference Example 89; 32.5 mg, 0.0698 mmol) in pyridine (0.7 mL) was added methanesulfonyl chloride (0.0270 mL, 0.349 mmol) at 0° C. After the resultant mixture was stirred at room temperature for 1.5 hr, the mixture was quenched with aqueous sodium hydrogen carbonate, diluted with ethyl acetate, washed with water and brine, dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The residue was diluted with N,N-dimethylformamide, and potassium carbonate (19.3 mg, 0.140 mmol) was added. After being stirred for 0.5 hr at 80° C., the reaction mixture was diluted with ethyl acetate, washed with water and brine, dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluting with a 10-60% ethyl acetate/n-hexane gradient mixture to give the title compound as a colorless solid (30.5 mg, 0.0684 mmol, 98%).

Workup

  1. customthe mixture was quenched with aqueous sodium hydrogen carbonate
  2. additiondiluted with ethyl acetate
  3. washwashed with water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. additionwas added
  8. washwashed with water and brine
  9. dry with materialdried over anhydrous sodium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo
  12. customThe residue was purified by flash column chromatography on silica gel eluting with a 10-60% ethyl acetate/n-hexane gradient mixture

Sources & evidence

ORD record
ord-7155b039b48341ec90305851556ae340
Source dataset
uspto-grants-2014_12
Patent number
US08901141B2

Reaction notes

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