m-Chloroperbenzoic acid → HCID 86608270, compound

HRID 2233913Notes

Reaction equation

HRID 2233913 reaction equation
C1C=C(Cl)C=C(C(OO)=[O:9])C=1.[Cl:12][C:13]1[C:17]([Cl:18])=[C:16]([CH3:19])[NH:15][C:14]=1[C:20]([NH:22][CH:23]1[CH2:28][CH2:27][N:26]([C:29]2[N:34]=[C:33]([S:35][CH3:36])[N:32]=[C:31]([C:37]([NH:39][O:40][CH3:41])=[O:38])[CH:30]=2)[CH2:25][CH2:24]1)=[O:21]>C(Cl)Cl>[Cl:12][C:13]1[C:17]([Cl:18])=[C:16]([CH3:19])[NH:15][C:14]=1[C:20]([NH:22][CH:23]1[CH2:28][CH2:27][N:26]([C:29]2[N:34]=[C:33]([S:35]([CH3:36])=[O:9])[N:32]=[C:31]([C:37]([NH:39][O:40][CH3:41])=[O:38])[CH:30]=2)[CH2:25][CH2:24]1)=[O:21]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 86608266HCID 86608266, compound

Product 1

HCID 86608270HCID 86608270, compoundYield 26.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

mCPBA (70%, 86 mg, 0.35 mmol) was added to a suspension of 6-(4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}piperidin-1-yl)-N-methoxy-2-(methylthio)pyrimidine-4-carboxamide (Example 8, 166 mg, 0.35 mmol) in DCM (12 ml) at 0° C. and the resultant mixture was stirred for 2 h. The reaction mixture was diluted with DCM (50 ml), washed with Na2SO3 solution (5%, 10 ml), dried over Na2SO4, filtered and concentrated under vacuum. Purification by reversed-phase HPLC (water/acetonitrile gradient, 10-95%) gave 45 mg of the title product.

Workup

  1. washwashed with Na2SO3 solution (5%, 10 ml)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum
  5. customPurification by reversed-phase HPLC (water/acetonitrile gradient, 10-95%)

Sources & evidence

ORD record
ord-2fb78f91f7b54a4fb4408f0ab0f1ec69
Source dataset
uspto-grants-2010_05
Patent number
US07709503B2

Reaction notes

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