Methanesulfonyl chloride → HCID 57786252, compound

HRID 1399224Notes

Reaction equation

HRID 1399224 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:24]([CH2:27][CH3:28])[CH2:25][CH3:26])=[CH:20][C:21]([F:23])=[CH:22][C:12]=2[N:11]=1.CS(Cl)(=O)=O>N1C=CC=CC=1>[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:24]([CH2:27][CH3:28])[CH2:25][CH3:26])[CH:20]=[C:21]([F:23])[CH:22]=3)[N:14]2[CH2:15][CH2:16][CH2:17]1

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 68764844HCID 68764844, compound

Product 1

HCID 57786252HCID 57786252, compoundYield 92.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirred solution of 3-{2-[(2,4-dichlorophenyl)amino]-7-(diethylamino)-5-fluoro-1H-benzimidazol-1-yl}propan-1-ol (Reference example 176, 170 mg, 0.400 mmol) in pyridine (2 mL) was added methanesulfonyl chloride (61.9 μL, 0.800 mol) at 0° C. After being stirred for 2.5 h, the reaction mixture was quenched with aqueous sodium hydrogen carbonate, diluted with ethyl acetate, washed with water and brine, dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by column chromatography on silica gel to give the title compound as a colorless solid (150 mg, 0.369 mmol, 92%).

Workup

  1. customthe reaction mixture was quenched with aqueous sodium hydrogen carbonate
  2. additiondiluted with ethyl acetate
  3. washwashed with water and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-b75e933fecb942a691f7cc472eb4d05d
Source dataset
uspto-grants-2014_12
Patent number
US08901141B2

Reaction notes

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