1,4-Dioxane → HCID 54562027, compound

HRID 353995Notes

Reaction equation

HRID 353995 reaction equation
[F:1][C:2]([F:35])([F:34])[C:3]1[CH:4]=[C:5]([CH:27]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:29]=1)[CH2:6][N:7]([CH3:26])[C:8]([C:10]1[C:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:14][N:13]=[C:12](S(C)(=O)=O)[N:11]=1)=[O:9].O1[CH2:41][CH2:40]OCC1>>[F:1][C:2]([F:35])([F:34])[C:3]1[CH:4]=[C:5]([CH:27]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:29]=1)[CH2:6][N:7]([CH3:26])[C:8]([C:10]1[C:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:14][N:13]=[C:12]([N:11]2[CH2:41][CH2:40][N:7]([CH3:6])[CH2:8][CH2:10]2)[N:11]=1)=[O:9]

Participants

3

Reactant 2

HCID 312751,4-DioxaneHCID 54161888HCID 54161888, compound

Product 1

HCID 54562027HCID 54562027, compoundYield 96.2%

Procedure

To a solution of 0.3 g (0.58 mmol) 2-methanesulfonyl-5-phenyl-pyrimidine-4-carboxylic acid (3,5-bis-trifluoromethyl-benzyl)-methyl-amide in 10 ml dioxan 0.16 ml (1.45 mmol) 1-methyl-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 H2O. 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 0.15 g (48%) 2-(4-methyl-piperazin-1-yl)-5-phenyl-pyrimidine-4-carboxylic acid (3,5-bis-trifluoromethyl-benzyl)-methyl-amide as a off-white solid, m.p. 162.0-162.8°.

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-da4f66ac09544e1990571f50f71ac999
Source dataset
uspto-grants-2004_06
Patent number
US06756380B1

Reaction notes

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