Dimethylamine → N'-[5-[4-(benzyloxy)phenyl]-1-(4-methoxy-phenyl)-1H-pyrazol-3-yl]-N,N-dimethylurea

HRID 351248Notes

Reaction equation

HRID 351248 reaction equation
[C:1]([N:8]1[CH:12]=[CH:11]N=C1)([N:3]1[CH:7]=CN=[CH:4]1)=[O:2].[CH2:13]([O:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2[N:31]([C:32]3[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][CH:33]=3)[N:30]=C(N)C=2)=[CH:23][CH:22]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.CNC>CN1CCCC1=O.C1COCC1>[CH2:13]([O:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2[N:31]([C:32]3[CH:33]=[CH:34][C:35]([O:38][CH3:39])=[CH:36][CH:37]=3)[N:30]=[C:12]([NH:8][C:1](=[O:2])[N:3]([CH3:4])[CH3:7])[CH:11]=2)=[CH:23][CH:22]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 674DimethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 210909885-[4-(Benzyloxy)phenyl]-1-(4-methoxyphenyl)-1H-pyrazol-3-amine

Product 1

HCID 21091147N'-[5-[4-(benzyloxy)phenyl]-1-(4-methoxy-phenyl)-1H-pyrazol-3-yl]-N,N-dimethylureaYield 82.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Carbonyldiimidazole (1.26 g) was added to a solution of 5-[4-(benzyloxy)phenyl]-1-(4-methoxyphenyl)-3-amino-1H-pyrazole (2.4 g) in 1-methyl-2-pyrrolidinone (22 ml). After stirring at ambient temperature for 2 hour, 2M solution of dimethylamine in THF (7.4 ml) was added and the mixture was stirred ambient temperature for 2 hour. The reaction mixture was partitioned between ethyl acetate and H2O. The organic layer was washed with saturated aqueous sodium chloride solution, dried over magnesium sulfate, and concentrated in vacuo. The residue was purified by silica gel column chromatography eluted with AcOEt/n-hexane=80% to give N′-[5-[4-(benzyloxy)phenyl]-1-(4-methoxyphenyl)-1H-pyrazol-3-yl]-N,N-dimethylurea (2.35 g) as amorphous powder.

Workup

  1. stirringthe mixture was stirred ambient temperature for 2 hour
  2. customThe reaction mixture was partitioned between ethyl acetate and H2O
  3. washThe organic layer was washed with saturated aqueous sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel column chromatography
  7. washeluted with AcOEt/n-hexane=80%

Sources & evidence

ORD record
ord-34b616b6ce8443efbd8904387c722a0c
Source dataset
uspto-grants-2007_02
Patent number
US07183306B2

Reaction notes

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