Methanesulfonyl chloride → HCID 57785862, compound

HRID 1398976Notes

Reaction equation

HRID 1398976 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]O)[C:13]2[C:19]([N:23]([CH2:26][CH3:27])[CH2:24][CH3:25])=[CH:20][CH:21]=[CH:22][C:12]=2[N:11]=1.CS(Cl)(=O)=O>N1C=CC=CC=1.C(=O)([O-])O.[Na+]>[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:19]([N:23]([CH2:26][CH3:27])[CH2:24][CH3:25])[CH:20]=[CH:21][CH:22]=3)[N:14]2[CH2:15][CH2:16][CH2:17]1

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 68770584HCID 68770584, compound

Product 1

HCID 57785862HCID 57785862, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of 3-[2-[(2,4-dichlorophenyl)amino]-7-(diethylamino)-1H-benzimidazol-1-yl]propan-1-ol (Reference Example 29; 35.7 mg, 0.0876 mmol) in pyridine (1 mL) was added methanesulfonyl chloride (0.0339 mL, 0.438 mmol) at 0° C. After the resultant mixture was stirred at room temperature 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 purified by flash column chromatography on silica gel eluting with a 10-40% ethyl acetate/n-hexane gradient mixture to give the title compound as a solid (29.2 mg, 0.0750 mmol, 86%). Analytically pure material was obtained by recrystallization from ethyl acetate/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. customThe residue was purified by flash column chromatography on silica gel eluting with a 10-40% ethyl acetate/n-hexane gradient mixture

Sources & evidence

ORD record
ord-bd4fc99559004ea0a181cffa5e08514e
Source dataset
uspto-grants-2014_12
Patent number
US08901141B2

Reaction notes

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