1,4-Dioxane → HCID 54499180, compound

HRID 354012Notes

Reaction equation

HRID 354012 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:26]=[C:27]([Cl:29])[CH:28]=1)[CH2:5][NH:6][C:7]([C:9]1[C:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH3:21])=[CH:13][N:12]=[C:11](S(C)(=O)=O)[N:10]=1)=[O:8].O1[CH2:35][CH2:34]OCC1>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:26]=[C:27]([Cl:29])[CH:28]=1)[CH2:5][NH:6][C:7]([C:9]1[C:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH3:21])=[CH:13][N:12]=[C:11]([N:10]2[CH2:35][CH2:34][N:6]([CH3:5])[CH2:7][CH2:9]2)[N:10]=1)=[O:8]

Participants

3

Reactant 2

HCID 312751,4-DioxaneHCID 54309794HCID 54309794, compound

Product 1

HCID 54499180HCID 54499180, compoundYield 175.9%

Procedure

To a solution of 0.19 g (0.435 mmol) 2-methanesulfonyl-5-o-tolyl-pyrimidine-4-carboxylic acid 3,5-dichloro-benzylamide in 5 ml dioxane 0.12 ml (1.08 mmol) 1-methylpiperazine was added. The reaction mixture was stirred for 16 hrs. After evaporation of the solvent, the residue was distributed between 5 ml CH2Cl2 and 25 ml H2O. The aqueous layer was extracted with 20 ml CH2Cl2, the combined organic layers were dried (MgSO4), filtered and evaporated. The residue was purified by chromatography (SiO2, CH2Cl2/MeOH 9:1) to give 0.18 g (88%) 2-(4-methyl-piperazin-1-yl)-5-o-tolyl-pyrimidine-4-carboxylic acid 3,5-dichloro-benzylamide as a colorless oil, MS (ISP): 470.2, 472.2 (M+H+).

Workup

  1. customAfter evaporation of the solvent
  2. extractionThe aqueous layer was extracted with 20 ml CH2Cl2
  3. dry with materialthe combined organic layers were dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by chromatography (SiO2, CH2Cl2/MeOH 9:1)

Sources & evidence

ORD record
ord-eb36ec60f12545439c942b7c69fa0dcd
Source dataset
uspto-grants-2004_06
Patent number
US06756380B1

Reaction notes

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