Dimethyl Sulfoxide → 1-[6-(4-Bromo-2-chloro-phenylamino)-7-fluoro-3H-benzoimidazol-5-yl]-2-methoxymethoxy-ethanone

HRID 216475Notes

Reaction equation

HRID 216475 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[Br:11][C:12]1[CH:17]=[CH:16][C:15]([NH:18][C:19]2[C:20]([CH:29]([OH:35])[CH2:30][O:31][CH2:32][O:33][CH3:34])=[CH:21][C:22]3[NH:26][CH:25]=[N:24][C:23]=3[C:27]=2[F:28])=[C:14]([Cl:36])[CH:13]=1>C(Cl)Cl.O>[Br:11][C:12]1[CH:17]=[CH:16][C:15]([NH:18][C:19]2[C:20]([C:29](=[O:35])[CH2:30][O:31][CH2:32][O:33][CH3:34])=[CH:21][C:22]3[NH:26][CH:25]=[N:24][C:23]=3[C:27]=2[F:28])=[C:14]([Cl:36])[CH:13]=1

Participants

6

Reactant 3

HCID 679Dimethyl SulfoxideHCID 65578Oxalyl chlorideHCID 673451521-[6-(4-Bromo-2-chloro-phenylamino)-7-fluoro-3H-benzoimidazol-5-yl]-2-methoxymethoxy-ethanol

Product 1

HCID 211141691-[6-(4-Bromo-2-chloro-phenylamino)-7-fluoro-3H-benzoimidazol-5-yl]-2-methoxymethoxy-ethanone

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent3×

Procedure

To a solution of oxalyl chloride (0.11 mL, 0.22 mmol) in CH2Cl2 (1 mL) at −78° C. is added DMSO (0.016 mL, 0.22 mmol). After stirring for 3 minutes, a solution of 1-[6-(4-bromo-2-chloro-phenylamino)-7-fluoro-3H-benzoimidazol-5-yl]-2-methoxymethoxy-ethanol 10l (25 mg, 0.056 mmol) in methylene chloride (1 mL) is added. The resulting solution is stirred for 30 minutes at −78° C. TEA (0.1 mL, 0.71 mmol) is added. The reaction mixture is slowly warmed to room temperature, stirred for 5 minutes at room temperature, and diluted with water and CH2Cl2. The organic layer is separated, dried over MgSO4, filtered, and concentrated to give the crude product which is directly used without further purification.

Workup

  1. stirringThe resulting solution is stirred for 30 minutes at −78° C
  2. stirringstirred for 5 minutes at room temperature
  3. customThe organic layer is separated
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-3c43297cc1134f2a847e5c981c077288
Source dataset
uspto-grants-2012_06
Patent number
US08193229B2

Reaction notes

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