m-Chloroperbenzoic acid → HCID 89488469, compound

HRID 570765Notes

Reaction equation

HRID 570765 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([C:8]([F:17])([C:13]([F:16])([F:15])[F:14])[C:9]([F:12])([F:11])[F:10])[CH:5]=[C:4]([Br:18])[C:3]=1[N:19]([CH3:40])[C:20]([C:22]1[C:23]([O:38][CH3:39])=[C:24]([N:28](C)[C:29]([C:31]2[CH:36]=[CH:35][N:34]=[CH:33][CH:32]=2)=[O:30])[CH:25]=[CH:26][CH:27]=1)=[O:21].ClC1C=CC=C(C(OO)=[O:49])C=1>ClCCl>[Br:1][C:2]1[CH:7]=[C:6]([C:8]([F:17])([C:13]([F:16])([F:15])[F:14])[C:9]([F:12])([F:11])[F:10])[CH:5]=[C:4]([Br:18])[C:3]=1[N:19]([CH3:40])[C:20]([C:22]1[C:23]([O:38][CH3:39])=[C:24]([NH:28][C:29]([C:31]2[CH:36]=[CH:35][N+:34]([O-:49])=[CH:33][CH:32]=2)=[O:30])[CH:25]=[CH:26][CH:27]=1)=[O:21]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 71547715HCID 71547715, compound

Product 1

HCID 89488469HCID 89488469, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of N-[3-[[2,6-dibromo-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]-methyl-carbamoyl]-2-methoxy-phenyl]-N-methyl-pyridine-4-carboxamide (Example G-17) (0.0657 g, 0.178 mmole) in dichloromethane (1.08 ml) was added by small portions 3-chloroperbenzoic acid (purity 70%) (0.0657 g, 0.266 mmole). After 2.5 hours stirring at 25° C., the yellow solution was quenched with aqueous sodium sulfite, diluted with dichloromethane and washed twice with saturated aqueous sodium bicarbonate, then with brine. The organic solution was dried over sodium sulfate. The product was isolated after removal of the solvent, as a white powder (melting range: 134-230° C.) showing, by LC-MS analysis (method 6 described hereunder) a retention time of 1.03 min and a M+H+ peak of 702.

Workup

  1. customthe yellow solution was quenched with aqueous sodium sulfite
  2. additiondiluted with dichloromethane
  3. washwashed twice with saturated aqueous sodium bicarbonate
  4. dry with materialThe organic solution was dried over sodium sulfate
  5. customThe product was isolated
  6. customafter removal of the solvent

Sources & evidence

ORD record
ord-14181bc65faa431094b423d8cdcdd29f
Source dataset
uspto-grants-2015_05
Patent number
US09023873B2

Reaction notes

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