Potassium Carbonate → HCID 57785860, compound

HRID 1399040Notes

Reaction equation

HRID 1399040 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[N:14]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]O)[C:13]2[C:21]([N:25]([CH2:28][CH3:29])[CH2:26][CH3:27])=[CH:22][CH:23]=[CH:24][C:12]=2[N:11]=1.CS(Cl)(=O)=O.C(=O)([O-])[O-].[K+].[K+]>N1C=CC=CC=1.C(=O)([O-])O.[Na+].C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:10]2=[N:11][C:12]3[C:13](=[C:21]([N:25]([CH2:28][CH3:29])[CH2:26][CH3:27])[CH:22]=[CH:23][CH:24]=3)[N:14]2[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 31297Methanesulfonyl chlorideHCID 68773304HCID 68773304, compound

Product 1

HCID 57785860HCID 57785860, compoundYield 76%

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of 5-[2-[(2,4-dichlorophenyl)amino]-7-(diethylamino)-1H-benzimidazol-1-yl]pentan-1-ol (Reference Example 113; 100 mg, 0.230 mmol) in pyridine (2 mL) was added methanesulfonyl chloride (0.0890 mL, 1.15 mmol) at 0° C. After the resultant mixture was stirred at 0° C. for 2 hr, the mixture was diluted with aqueous sodium hydrogen carbonate and extracted with ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was diluted with N,N-dimethylformamide (5 mL) and to the solution was added potassium carbonate (63.5 mg, 0.460 mmol) at room temperature. After the resultant mixture was stirred at 80° C. for 2 hr, the 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 0-30% ethyl acetate/n-hexane gradient mixture to give the title compound as a solid (72.6 mg, 0.174 mmol, 76%). Analytically pure material was obtained by recrystallization from n-hexane.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. additionThe residue was diluted with N,N-dimethylformamide (5 mL) and to the solution
  7. washwashed with water and brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customThe residue was purified by flash column chromatography on silica gel eluting with a 0-30% ethyl acetate/n-hexane gradient mixture

Sources & evidence

ORD record
ord-a718f21ac1fd40f59bf3674cdaf5ccd0
Source dataset
uspto-grants-2014_12
Patent number
US08901141B2

Reaction notes

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