Water → HCID 10229757, compound

HRID 1018572Notes

Reaction equation

HRID 1018572 reaction equation
[F:1][C:2]([F:34])([F:33])[C:3]1[CH:4]=[C:5]([CH:26]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:28]=1)[C:6]([N:8]1[CH2:25][CH2:24][C:11]2([N:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[Cl:22])[CH2:14][NH:13][C:12]2=[O:23])[CH2:10][CH2:9]1)=[O:7].[H-].[Na+].[CH3:37]I.O>COCCOC>[F:32][C:29]([F:31])([F:30])[C:27]1[CH:26]=[C:5]([CH:4]=[C:3]([C:2]([F:1])([F:33])[F:34])[CH:28]=1)[C:6]([N:8]1[CH2:9][CH2:10][C:11]2([N:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[Cl:22])[CH2:14][N:13]([CH3:37])[C:12]2=[O:23])[CH2:24][CH2:25]1)=[O:7]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 18401647HCID 18401647, compound

Product 1

HCID 10229757HCID 10229757, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

8-(3,5-Bis-trifluoromethyl-benzoyl)-1-(2-chloro-phenyl)-1,3,8-triaza-spiro[4.5]decan-4-one (253 mg) was suspended in 1,2-dimethoxyethane (3 mL) and sodium hydride (24 mg, 60%) was added with stirring at room temperature. After 15 minutes methyliodide (78 mg) was added and stirring was continued overnight at room temperature. Water was added and the mixture was extracted with ethylacetate. Organic phases were pooled, dried with Na2SO4 and the solvent was evaporated. Chromatography on silica gel (hexane/ethylacetate=1:1) yielded the desired product (152 mg, 59%), MS: m/e=520.1 (M+H+).

Workup

  1. stirringstirring
  2. extractionthe mixture was extracted with ethylacetate
  3. dry with materialdried with Na2SO4
  4. customthe solvent was evaporated

Sources & evidence

ORD record
ord-fc43b81a13d24555af7281fa89bef6ea
Source dataset
uspto-grants-2002_11
Patent number
US06482829B2

Reaction notes

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