Acetyl chloride → HCID 59506988, compound

HRID 1800595Notes

Reaction equation

HRID 1800595 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:32])[C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[C:22]=3[Cl:31])[CH:15]=[CH:16][C:17]=1[CH3:18])[N:5]=2.[C:33](Cl)(=[O:35])[CH3:34].C(=O)([O-])O.[Na+]>N1C=CC=CC=1.CN(C)C1C=CN=CC=1>[C:33]([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:32])[C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:29])([F:28])[F:30])[C:22]=3[Cl:31])[CH:15]=[CH:16][C:17]=1[CH3:18])[N:5]=2)(=[O:35])[CH3:34]

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 516892Sodium BicarbonateHCID 86646040HCID 86646040, compound

Product 1

HCID 59506988HCID 59506988, compoundYield 74.6%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

To a solution of N-{3-[(2-amino[1,3]thiazolo[5,4-b]pyridin-5-yl)oxy]-4-methylphenyl}-2-chloro-3-(trifluoromethyl)benzamide (200 mg, 0.417 mmol) produced in Example C78(iv) in pyridine (5 mL) were added acetyl chloride (118 μL, 1.67 mmol) and N,N-dimethylpyridine-4-amine (6.2 mg, 0.0507 mmol), and the mixture was stirred at room temperature for 28 hr. To the reaction mixture was added saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate, and filtered through a pad filled with basic silica gel. The solvent was concentrated under reduced pressure, and the obtained crude product was recrystallized from ethyl acetate to give the title compound (162 mg, 74%) as white crystals.

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. filtrationfiltered through a pad
  5. additionfilled with basic silica gel
  6. concentrationThe solvent was concentrated under reduced pressure
  7. customthe obtained crude product
  8. customwas recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-6cb9604c72df4fe7ba9aee9af9fff3e2
Source dataset
uspto-grants-2013_01
Patent number
US08344135B2

Reaction notes

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