Diethyl Ether → HCID 68451230, compound

HRID 2353395Notes

Reaction equation

HRID 2353395 reaction equation
[CH:1]1([NH:4][C:5](=[O:30])[C:6]2[CH:11]=[C:10]([C:12]3[C:26]([F:27])=[CH:25][C:15]4[C:16]([C:19]5[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=5)=[N:17][O:18][C:14]=4[CH:13]=3)[C:9]([CH3:28])=[C:8]([F:29])[CH:7]=2)[CH2:3][CH2:2]1.C1C=C(Cl)C=C(C(OO)=[O:39])C=1.CCOCC>C(Cl)(Cl)Cl>[CH:1]1([NH:4][C:5](=[O:30])[C:6]2[CH:11]=[C:10]([C:12]3[C:26]([F:27])=[CH:25][C:15]4[C:16]([C:19]5[CH:20]=[CH:21][N+:22]([O-:39])=[CH:23][CH:24]=5)=[N:17][O:18][C:14]=4[CH:13]=3)[C:9]([CH3:28])=[C:8]([F:29])[CH:7]=2)[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 70297m-Chloroperbenzoic acidHCID 11188919HCID 11188919, compound

Product 1

HCID 68451230HCID 68451230, compoundYield 72.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
60 °C

Procedure

A solution of N-cyclopropyl-3-fluoro-5-[5-fluoro-3-(4-pyridinyl)-1,2-benzisoxazol-6-yl]-4-methylbenzamide (Example 3, 12 mg) in chloroform (1 ml) under nitrogen was treated with M-CPBA (10 mg) and the mixture was stirred at 60° C. for 40 min. Further m-CPBA (10 mg) was added and stirring was continued for 1 h. The solution was applied to an Isolute amino cartridge (1 g) which was eluted with chloroform/methanol (100:0 to 90:10) to give a glass. Trituration using a small quantity of ether gave the title compound as a white powder (9 mg).

Workup

  1. stirringstirring
  2. waitwas continued for 1 h
  3. washwas eluted with chloroform/methanol (100:0 to 90:10)
  4. customto give a glass

Sources & evidence

ORD record
ord-a78dc81ee47b442ab62a7bcd2e945399
Source dataset
uspto-grants-2010_07
Patent number
US07750026B2

Reaction notes

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