Chloroacetyl chloride → HCID 86645996, compound

HRID 1800442Notes

Reaction equation

HRID 1800442 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[C:9]([N:10]=1)=[CH:8][CH:7]=[C:6]([O:11][C:12]1[CH:13]=[C:14]([NH:19][C:20](=[O:31])[C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[CH:22]=3)[CH:15]=[CH:16][C:17]=1[CH3:18])[N:5]=2.[Cl:32][CH2:33][C:34](Cl)=[O:35].C(=O)([O-])O.[Na+]>CN(C)C=O>[Cl:32][CH2:33][C:34]([NH:1][C:2]1[S:3][C:4]2[C:9]([N:10]=1)=[CH:8][CH:7]=[C:6]([O:11][C:12]1[CH:13]=[C:14]([NH:19][C:20](=[O:31])[C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[CH:22]=3)[CH:15]=[CH:16][C:17]=1[CH3:18])[N:5]=2)=[O:35]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 516892Sodium BicarbonateHCID 86645995HCID 86645995, compound

Product 1

HCID 86645996HCID 86645996, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-{3-[(2-amino[1,3]thiazolo[5,4-b]pyridin-5-yl)oxy]-4-methylphenyl}-3-(trifluoromethyl)benzamide (200 mg, 0.450 mmol) produced in Example C8(iv) in N,N-dimethylformamide (5 mL) was added chloroacetyl chloride (104 μL, 0.900 mmol), and the mixture was stirred at room temperature for 2 hr. Saturated aqueous sodium hydrogen carbonate solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and filtrated. The filtrate was concentrated under reduced pressure, and the obtained residue was washed with a mixed solution of ethyl acetate and hexane to give the title compound (218 mg, 93%) as a white powder. The powder was used for the next reaction without further purification operation.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltrated
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. washthe obtained residue was washed with a mixed solution of ethyl acetate and hexane

Sources & evidence

ORD record
ord-389faa1ebf4e455db95949e6ffcc1e0e
Source dataset
uspto-grants-2013_01
Patent number
US08344135B2

Reaction notes

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