Cyclopropanecarbonyl chloride → HCID 59506934, compound

HRID 1800594Notes

Reaction equation

HRID 1800594 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.[CH:33]1([C:36](Cl)=[O:37])[CH2:35][CH2:34]1>N1C=CC=CC=1.C(OCC)(=O)C>[Cl:31][C:22]1[C:23]([C:27]([F:29])([F:28])[F:30])=[CH:24][CH:25]=[CH:26][C:21]=1[C:20]([NH:19][C:14]1[CH:15]=[CH:16][C:17]([CH3:18])=[C:12]([O:11][C:6]2[N:5]=[C:4]3[S:3][C:2]([NH:1][C:36]([CH:33]4[CH2:35][CH2:34]4)=[O:37])=[N:10][C:9]3=[CH:8][CH:7]=2)[CH:13]=1)=[O:32]

Participants

5

Reactant 2

HCID 77637Cyclopropanecarbonyl chlorideHCID 86646040HCID 86646040, compound

Product 1

HCID 59506934HCID 59506934, compoundYield 50.4%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

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) in pyridine (5 mL) was added cyclopropanecarbonyl chloride (57.4 μL, 0.835 mmol), and the mixture was stirred at room temperature for 18 hr. The reaction mixture was diluted with ethyl acetate, washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, and dried over anhydrous magnesium sulfate. The residue was filtered through a pad filled with silica gel, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane=10/90→70/30), and recrystallized from tetrahydrofuran to give the title compound (115 mg, 50%) as white crystals.

Workup

  1. washwashed with saturated aqueous sodium hydrogen carbonate solution and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationThe residue was filtered through a pad
  4. additionfilled with silica gel
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane=10/90→70/30)
  7. customrecrystallized from tetrahydrofuran

Sources & evidence

ORD record
ord-e7db7269657545688d7c0b9379be8609
Source dataset
uspto-grants-2013_01
Patent number
US08344135B2

Reaction notes

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