Acetoxyacetyl chloride → HCID 59507020, compound

HRID 1800440Notes

Reaction equation

HRID 1800440 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.C([O:35][CH2:36][C:37](Cl)=[O:38])(=O)C>N1C=CC=CC=1>[C:36]([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])[CH2:37][OH:38]

Participants

4

Reactant 2

HCID 26297Acetoxyacetyl chlorideHCID 86645995HCID 86645995, compound

Product 1

HCID 59507020HCID 59507020, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

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 pyridine (5 mL) was added acetoxyacetyl chloride (121 μL, 1.12 mmol), and the mixture was stirred at room temperature for 30 min. The reaction mixture was concentrated under reduced pressure, and a mixture of the obtained residue, methanol (3 mL), pyridine (2 mL) and 0.5N aqueous sodium hydroxide solution (3 mL) was stirred at room temperature for 16 hr. Water 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 solvent was evaporated under reduced pressure, and the residue was precipitated with ethyl acetate and hexane to give the title compound (92 mg, 41%) as a white powder.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additiona mixture of the obtained residue, methanol (3 mL), pyridine (2 mL) and 0.5N aqueous sodium hydroxide solution (3 mL)
  3. stirringwas stirred at room temperature for 16 hr
  4. additionWater was added to the reaction mixture
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe extract was washed with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltrated
  9. customThe solvent was evaporated under reduced pressure
  10. customthe residue was precipitated with ethyl acetate and hexane

Sources & evidence

ORD record
ord-a231f71e60504129a009dc02e41644e7
Source dataset
uspto-grants-2013_01
Patent number
US08344135B2

Reaction notes

Loading…