m-Chloroperbenzoic acid → HCID 89488421, compound

HRID 570764Notes

Reaction equation

HRID 570764 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]([CH3:37])[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:9]([F:10])([F:11])[F:12])[C:13]([F:14])([F:15])[F:16])[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]([CH3:37])[C:29]([C:31]2[CH:32]=[CH:33][N+:34]([O-:49])=[CH:35][CH:36]=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 89488421HCID 89488421, 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) (0.051 g, 0.073 mmole) in dichloromethane (0.44 ml) was added by small portions 3-chloroperbenzoic acid (purity 70%) (0.027 g, 0.11 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 (Compound G18 of Table G) was isolated after removal of the solvent, as a white powder (melting range: 105-194° C.) showing, by LC-MS analysis (method 6 described hereunder) a retention time of 0.99 min and a M+H+ peak of 716.

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 (Compound G18 of Table G) was isolated
  6. customafter removal of the solvent

Sources & evidence

ORD record
ord-649c246f0e29467595ef3cad8f6deb7d
Source dataset
uspto-grants-2015_05
Patent number
US09023873B2

Reaction notes

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