m-Chloroperbenzoic acid → HCID 118094028, compound

HRID 515533Notes

Reaction equation

HRID 515533 reaction equation
[CH:1]1([NH:6][S:7]([C:10]2[C:11]3[CH:12]=[CH:13][CH:14]=[N:15][C:16]=3[CH:17]=[C:18]([C:20]3[C:21]([CH3:26])=[N:22][O:23][C:24]=3[CH3:25])[CH:19]=2)(=[O:9])=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1.C1C=C([Cl:33])C=C(C(OO)=O)C=1>ClCCl.C(OCC)(=O)C>[Cl:33][C:14]1[CH:13]=[CH:12][C:11]2[C:10]([S:7]([NH:6][CH:1]3[CH2:2][CH2:3][CH2:4][CH2:5]3)(=[O:9])=[O:8])=[CH:19][C:18]([C:20]3[C:21]([CH3:26])=[N:22][O:23][C:24]=3[CH3:25])=[CH:17][C:16]=2[N:15]=1

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 118093990HCID 118093990, compound

Product 1

HCID 118094028HCID 118094028, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of N-cyclopentyl-7-(3,5-dimethylisoxazol-4-yl)quinoline-5-sulfonamide (272 mg, 0.73 mmol) and mCPBA (max 77% by weight, 364 mg) in dichloromethane (5 mL) was stirred at room temperature for 2 hours. The reaction mixture was diluted with ethyl acetate and washed with aqueous sodium sulfite solution followed by brine. The organic layer was dried over sodium sulfate and concentrated. The residue was dissolved in POCl3 and heated at 80° C. for 1 hour. The reaction mixture was concentrated before being partitioned between ethyl acetate and aqueous sodium bicarbonate. The organic phase was dried over sodium sulfate and purified on silica gel (rf=0.42 in 2:1 hexanes:ethyl acetate) to give 2-chloro-N-cyclopentyl-7-(3,5-dimethylisoxazol-4-yl)quinoline-5-sulfonamide.

Workup

  1. washwashed with aqueous sodium sulfite solution
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. concentrationconcentrated
  4. dissolutionThe residue was dissolved in POCl3
  5. temperatureheated at 80° C. for 1 hour
  6. concentrationThe reaction mixture was concentrated
  7. custombefore being partitioned between ethyl acetate and aqueous sodium bicarbonate
  8. dry with materialThe organic phase was dried over sodium sulfate
  9. custompurified on silica gel (rf=0.42 in 2:1 hexanes:ethyl acetate)

Sources & evidence

ORD record
ord-57c5240992d14dc9bcfe70659ed2ded7
Source dataset
uspto-grants-2015_08
Patent number
US09108953B2

Reaction notes

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