m-Chloroperbenzoic acid → HCID 57990197, compound

HRID 245607Notes

Reaction equation

HRID 245607 reaction equation
[CH3:1][C:2]([NH:7][C:8]([C:10]1[C:11]([NH:19][C:20]([C:22]2[N:23]([C:31]3[C:36]([Cl:37])=[CH:35][CH:34]=[CH:33][N:32]=3)[N:24]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:26]=2)=[O:21])=[CH:12][CH:13]=[C:14]2[C:18]=1[NH:17][N:16]=[CH:15]2)=[O:9])([CH3:6])[CH2:3][S:4][CH3:5].ClC1C=CC=C(C(OO)=[O:46])C=1>C(Cl)Cl.C(OCC)(=O)C>[CH3:5][S:4]([CH2:3][C:2]([NH:7][C:8]([C:10]1[C:11]([NH:19][C:20]([C:22]2[N:23]([C:31]3[C:36]([Cl:37])=[CH:35][CH:34]=[CH:33][N:32]=3)[N:24]=[C:25]([C:27]([F:30])([F:28])[F:29])[CH:26]=2)=[O:21])=[CH:12][CH:13]=[C:14]2[C:18]=1[NH:17][N:16]=[CH:15]2)=[O:9])([CH3:1])[CH3:6])=[O:46]

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 57990165HCID 57990165, compound

Product 1

HCID 57990197HCID 57990197, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 144 mg (0.26 mmol) of 6-{[2-(3-chloro-pyridin-2-yl)-5-trifluoromethyl-2H-pyrazole-3-carbonyl]-amino}-1H-indazole-7-carboxylic acid (1,1-dimethyl-2-methylsulfanylethyl)-amide, prepared in example 7 in 2.88 mL of methylene chloride at 0° C. is added dropwise 64 mg (0.26 mmol) of m-chloroperbenzoic acid dissolved in 0.5 mL of methylene chloride. The mixture is stirred and let warm-up to ambient temperature within 1 hour. The reaction is quenched by the addition of an aqueous saturated sodium carbonate solution. The product is extracted with ethyl acetate (3 times) and the combined organic extracts are dried on Na2SO4, filtrated and evaporated. After a flash chromatography with hexanes and ethyl acetate as eluents, 111 mg (0.17 mmol, 75%) of a white solid are obtained; LC/MS: 568/570 (M+H)+.

Workup

  1. customThe reaction is quenched by the addition of an aqueous saturated sodium carbonate solution
  2. extractionThe product is extracted with ethyl acetate (3 times)
  3. customthe combined organic extracts are dried on Na2SO4
  4. filtrationfiltrated
  5. customevaporated

Sources & evidence

ORD record
ord-907501e5e01048baa81ff1aa391f0ea6
Source dataset
uspto-grants-2014_02
Patent number
US08658801B2

Reaction notes

Loading…