m-Chloroperbenzoic acid → HCID 118094030, compound

HRID 515543Notes

Reaction equation

HRID 515543 reaction equation
[CH:1]1([NH:6][S:7]([C:10]2[C:11]3[N: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)C=C(C(OO)=[O:35])C=1>ClCCl>[CH:1]1([NH:6][S:7]([C:10]2[CH:19]=[C:18]([C:20]3[C:21]([CH3:26])=[N:22][O:23][C:24]=3[CH3:25])[CH:17]=[C:16]3[C:11]=2[N:12]=[CH:13][CH:14]=[N+:15]3[O-:35])(=[O:8])=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acid2×HCID 118094038HCID 118094038, compound

Product 1

HCID 118094030HCID 118094030, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of N-cyclopentyl-7-(3,5-dimethylisoxazol-4-yl)quinoxaline-5-sulfonamide (0.069 g, 0.18 mmol) and mCPBA (max 77% by weight, 0.083 g, 0.37 mM) in dichloromethane (3 mL) was stirred at room temperature for 2 hours. Additional mCPBA (0.166 g, 0.74 mM) was added and the reaction stirred for 16 hours at room temperature. Volatiles were removed under reduced pressure and the crude product purified by preparatory HPLC (5-95% MeCN/H2O, 0.1% TFA) to afford the product as a white solid.

Workup

  1. stirringthe reaction stirred for 16 hours at room temperature
  2. customVolatiles were removed under reduced pressure
  3. customthe crude product purified by preparatory HPLC (5-95% MeCN/H2O, 0.1% TFA)

Sources & evidence

ORD record
ord-6d69e6208867445d81de66b8a42b5848
Source dataset
uspto-grants-2015_08
Patent number
US09108953B2

Reaction notes

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