Sodium Acetate → HCID 69331771, compound

HRID 351250Notes

Reaction equation

HRID 351250 reaction equation
[O-:1][C:2]#[N:3].[K+].Cl.[NH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[N:20]([C:21]3[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=3)[N:19]=[C:18]([NH:29][C:30](=[O:34])[N:31]([CH3:33])[CH3:32])[CH:17]=2)=[CH:12][CH:11]=1.C([O-])(=O)C.[Na+]>O.CN(C=O)C>[NH2:3][C:2]([NH:6][CH2:7][CH2:8][O:9][C:10]1[CH:11]=[CH:12][C:13]([C:16]2[N:20]([C:21]3[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=3)[N:19]=[C:18]([NH:29][C:30](=[O:34])[N:31]([CH3:33])[CH3:32])[CH:17]=2)=[CH:14][CH:15]=1)=[O:1]

Participants

6

Reactant 3

HCID 517045Sodium AcetateHCID 11378442Potassium cyanateHCID 21091142HCID 21091142, compound

Product 1

HCID 69331771HCID 69331771, compoundYield 49.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent3×HCID 6228DimethylformamideSolvent

Procedure

A solution of potassium cyanate (64.9 mg) in H2O (0.5 ml) was added to a solution of N′-[5-[4-(2-aminoethoxy)phenyl]-1-(4-methoxy-phenyl)-1H-pyrazol-3-yl]-N,N-dimethylurea hydrochloride (172.8 mg) and sodium acetate (65.6 mg) in a mixture of DMF (1.5 ml) and H2O (0.5 ml). The reaction mixture was stirred at ambient temperature overnight. The mixture was diluted with H2O, partitioned between AcOEt and H2O. The aqueous layer was reextracted with AcOEt. saturated aqueous sodium chloride solution, dried over magnesium sulfate, and concentrated in vacuo. The residue was purified by preparative thin layer silica gel chromatography developed by 10% MeOH/CHCl3. The separated silica gel was extracted with 10% MeOH/CHCl3 and the solvent was evaporated in vacuo. The residue was crystallized from AcOEt-IPE to give N′-[5-(4-{2-[(aminocarbonyl) -amino]ethoxy}phenyl)-1-(4-methoxyphenyl)-1H-pyrazol-3-yl]-N,N-dimethylurea (87.0 mg) as a powder.

Workup

  1. custompartitioned between AcOEt and H2O
  2. dry with materialsaturated aqueous sodium chloride solution, dried over magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by preparative thin layer silica gel chromatography
  5. extractionThe separated silica gel was extracted with 10% MeOH/CHCl3
  6. customthe solvent was evaporated in vacuo
  7. customThe residue was crystallized from AcOEt-IPE

Sources & evidence

ORD record
ord-c55a92b93e294fe89493e49ad87d7310
Source dataset
uspto-grants-2007_02
Patent number
US07183306B2

Reaction notes

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