m-Chloroperbenzoic acid → HCID 57833390, compound

HRID 729968Notes

Reaction equation

HRID 729968 reaction equation
[C:1]1([C:7]2[N:12]=[C:11]([NH2:13])[N:10]=[C:9]([NH:14][C:15]3[CH:20]=[CH:19][C:18]([O:21][C:22]4[CH:27]=[CH:26][N:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[CH:23]=4)=[CH:17][CH:16]=3)[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1C=C(Cl)C=C(C(OO)=[O:40])C=1>C(Cl)(Cl)Cl>[O-:40][N+:25]1[CH:26]=[CH:27][C:22]([O:21][C:18]2[CH:19]=[CH:20][C:15]([NH:14][C:9]3[CH:8]=[C:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[N:12]=[C:11]([NH2:13])[N:10]=3)=[CH:16][CH:17]=2)=[CH:23][C:24]=1[C:28]([F:30])([F:29])[F:31]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 57833410HCID 57833410, compound

Product 1

HCID 57833390HCID 57833390, compoundYield 11%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 6-phenyl-N4-(4-{[2-(trifluoromethyl)pyridin-4-yl]oxy}phenyl)pyrimidine-2,4-diamine (0.10 g, 0.24 mmol, Example 37) in CHCl3, m-CPBA (77%, 0.053 g, 0.24 mmol) was added and the mixture was stirred at rt overnight. Solvent was removed in vacuo, and the residue was taken up in DMF and purified by prep-HPLC to provide 11 mg of an off-white solid (11%). 1H NMR (DMSO-d6) 810.20 (s, 1H), 8.64 (d, J=5.7 Hz, 1H), 7.93 (s, 1H), 7.86-7.92 (m, 2H), 7.52-7.56 (m, 2H), 7.41-7.49 (m, 5H), 7.30-7.39 (m, 2H), 7.24 (dd, J=5.7 Hz, 1H), 6.71 (s, 1H). MS ES 440 (M+H)+, calcd 440, RT=2.97 min.

Workup

  1. customSolvent was removed in vacuo
  2. custompurified by prep-HPLC

Sources & evidence

ORD record
ord-76cb93c526ab47a197a2619e0397825f
Source dataset
uspto-grants-2009_09
Patent number
US07582646B2

Reaction notes

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