Hydrogen Peroxide → HCID 67132158, compound

HRID 245000Notes

Reaction equation

HRID 245000 reaction equation
[OH:1]O.[CH3:3][NH:4][C:5](=[O:37])[CH2:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[C:22](=S)[N:21]([C:24]3[CH:29]=[CH:28][C:27]([C:30]#[N:31])=[C:26]([C:32]([F:35])([F:34])[F:33])[CH:25]=3)[C:20](=[O:36])[C:16]32[CH2:19][CH2:18][CH2:17]3)=[CH:11][CH:10]=1>C(O)(=O)C>[CH3:3][NH:4][C:5](=[O:37])[CH2:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[C:22](=[O:1])[N:21]([C:24]3[CH:29]=[CH:28][C:27]([C:30]#[N:31])=[C:26]([C:32]([F:35])([F:34])[F:33])[CH:25]=3)[C:20](=[O:36])[C:16]32[CH2:19][CH2:18][CH2:17]3)=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 15951524HCID 15951524, compound

Product 1

HCID 67132158HCID 67132158, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Hydrogen peroxide (30%, 0.4) was added dropwise to a solution of N-methyl-4-{4-[7-(4-Cyano-3-trifluoromethylphenyl)-8-oxo-6-thioxo-5,7-diaza-spiro[3.4]oct-5-yl]phenyl}butanamide (42e) (0.032 g, 0.064 mmol) in glacial acetic acid (0.5 ml). The mixture was stirred at room temperature for 5 hours and then washed with water and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, concentrated and chromatographed (dichloromethane:acetone, 80:20) to yield N-methyl-4-{4-[7-(4-cyano-3-trifluoromethylphenyl)-6,8-dioxo-5,7-diazaspiro[3.4]oct-5-yl]-phenyl}butyramide (42g) [RD158] (0.029 g, 0.06 mmol, 94%), the structure of which is illustrated in Formula 9, as a white powder.

Workup

  1. washwashed with water
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. concentrationconcentrated
  5. customchromatographed (dichloromethane:acetone, 80:20)

Sources & evidence

ORD record
ord-9775965a2b714a09a6308c2bf6b5ff6d
Source dataset
uspto-grants-2014_02
Patent number
US08658681B2

Reaction notes

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