m-Chloroperbenzoic acid → HCID 86714758, compound

HRID 1055080Notes

Reaction equation

HRID 1055080 reaction equation
[CH3:1][C:2]([CH3:45])([CH3:44])[CH:3]([NH:16][C:17]1[C:22]([F:23])=[CH:21][N:20]=[C:19]([C:24]2[C:32]3[C:27](=[N:28][CH:29]=[C:30]([F:33])[CH:31]=3)[N:26]([S:34]([C:37]3[CH:43]=[CH:42][C:40]([CH3:41])=[CH:39][CH:38]=3)(=[O:36])=[O:35])[CH:25]=2)[N:18]=1)[CH2:4][CH2:5][Se]C1C=CC=CC=1[N+]([O-])=O.C1C=C(Cl)C=C(C(OO)=O)C=1>C(Cl)(Cl)Cl.ClCCl>[CH3:1][C:2]([CH3:45])([CH3:44])[CH:3]([NH:16][C:17]1[C:22]([F:23])=[CH:21][N:20]=[C:19]([C:24]2[C:32]3[C:27](=[N:28][CH:29]=[C:30]([F:33])[CH:31]=3)[N:26]([S:34]([C:37]3[CH:38]=[CH:39][C:40]([CH3:41])=[CH:42][CH:43]=3)(=[O:36])=[O:35])[CH:25]=2)[N:18]=1)[CH:4]=[CH2:5]

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 86714757HCID 86714757, compound

Product 1

HCID 86714758HCID 86714758, compoundYield 86.4%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

To a cold (0° C.) solution of racemic N-(4,4-dimethyl-1-((2-nitrophenyl)selanyl)pentan-3-yl)-5-fluoro-2-(5-fluoro-1-tosyl-1H-pyrrolo[2,3-b]yridin-3-yl)pyrimidin-4-amine, 88a, (1.01 g, 1.45 mmol) in chloroform (15 mL) was added mCPBA (0.40 g of 77%, 1.79 mmol). After stirring for 1 hour at room temperature, the mixture was diluted with dichloromethane (100 mL) and the resulting solution was washed with aqueous sodium bicarbonate solution. The organic phase was dried (MgSO4), filtered and concentrated in vacuo. The crude residue was purified by silica gel chromatography (0 to 100% EtOAc/Hexanes) to afford 623 mg of the desired product: LCMS Gradient 10-90%, 0.1% formic acid, 5 minutes, C18/ACN, (M+H) 496.76.

Workup

  1. washthe resulting solution was washed with aqueous sodium bicarbonate solution
  2. dry with materialThe organic phase was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude residue was purified by silica gel chromatography (0 to 100% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-2d389b015e454e0aa1678121adcfa97e
Source dataset
uspto-grants-2016_07
Patent number
US09394302B2

Reaction notes

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