Cyclopropanecarbonyl chloride → HCID 59507004, compound

HRID 1800439Notes

Reaction equation

HRID 1800439 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.[CH:32]1([C:35](Cl)=[O:36])[CH2:34][CH2:33]1>N1C=CC=CC=1>[CH:32]1([C:35]([NH:1][C:2]2[S:3][C:4]3[C:9]([N:10]=2)=[CH:8][CH:7]=[C:6]([O:11][C:12]2[CH:13]=[C:14]([NH:19][C:20](=[O:31])[C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[CH:22]=4)[CH:15]=[CH:16][C:17]=2[CH3:18])[N:5]=3)=[O:36])[CH2:34][CH2:33]1

Participants

4

Reactant 2

HCID 77637Cyclopropanecarbonyl chlorideHCID 86645995HCID 86645995, compound

Product 1

HCID 59507004HCID 59507004, compoundYield 56.4%

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) in pyridine (5 mL) was added cyclopropanecarbonyl chloride (77.5 μL, 1.12 mmol), and the mixture was stirred at room temperature for 16 hr. The reaction mixture was evaporated under reduced pressure, and a mixture of the obtained residue, methanol (3 mL) and 0.5N aqueous sodium hydroxide solution (3 mL) was stirred at room temperature for 30 min. 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 tetrahydrofuran to give the title compound (130 mg, 56%) as a white powder.

Workup

  1. customThe reaction mixture was evaporated under reduced pressure
  2. additiona mixture of the obtained residue, methanol (3 mL) and 0.5N aqueous sodium hydroxide solution (3 mL)
  3. stirringwas stirred at room temperature for 30 min
  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 tetrahydrofuran

Sources & evidence

ORD record
ord-bd59bb9973d14de3b65b0846038e7a22
Source dataset
uspto-grants-2013_01
Patent number
US08344135B2

Reaction notes

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