1,4-Dioxane → HCID 10167128, compound

HRID 1005985Notes

Reaction equation

HRID 1005985 reaction equation
[F:1][C:2]([F:39])([F:38])[C:3]1[CH:4]=[C:5]([C:13]([CH3:37])([CH3:36])[C:14]([N:16]([C:18]2[C:19]([O:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[CH3:35])=[N:20][C:21](S(C)(=O)=O)=[N:22][CH:23]=2)[CH3:17])=[O:15])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.O1[CH2:45][CH2:44]OCC1>>[F:1][C:2]([F:39])([F:38])[C:3]1[CH:4]=[C:5]([C:13]([CH3:37])([CH3:36])[C:14]([N:16]([CH3:17])[C:18]2[C:19]([O:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[CH3:35])=[N:20][C:21]([N:16]3[CH2:45][CH2:44][NH:22][CH2:23][CH2:18]3)=[N:22][CH:23]=2)=[O:15])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1

Participants

3

Reactant 2

HCID 312751,4-DioxaneHCID 22674305HCID 22674305, compound

Product 1

HCID 10167128HCID 10167128, compoundYield 132.3%

Procedure

To a solution of 0.30 g (0.52 mmol) 2-(3,5-bis-trifluoromethyl-phenyl)-N-(2-methanesulfonyl-4-o-tolyloxy-pyrimidin-5-yl)-N-methyl-isobutyramide in 10 ml dioxane 0.112 g (1.3 mmol) piperazine was added. The reaction mixture was stirred for 16 hrs. After evaporation of the solvent, the residue was distributed between 50 ml CH2Cl2 and 50 ml sat. NaHCO3-solution. The aqueous layer was extracted with 50 ml CH2Cl2, the combined organic layers dried (MgSO4), filtered and evaporated. The residue was purified by chromatography (SiO2, CH2Cl2/MeOH/NH4OH 140:10:1) to give 0.20 g (66%) 2-(3,5-bis-trifluoromethyl-phenyl)-N-methyl-N-(2-piperazin-1-yl-4-o-tolyloxy-pyrimidin-5-yl)-isobutyramide as a white foam, MS (ISP): 582.2 (M+H)+.

Workup

  1. customAfter evaporation of the solvent
  2. extractionThe aqueous layer was extracted with 50 ml CH2Cl2
  3. dry with materialthe combined organic layers dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by chromatography (SiO2, CH2Cl2/MeOH/NH4OH 140:10:1)

Sources & evidence

ORD record
ord-7af444ebf83e4f419fc4c4056cfd63bb
Source dataset
uspto-grants-2004_09
Patent number
US06787539B2

Reaction notes

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