Benzeneacetic acid, 3,4-dimethoxy-, methyl ester → HCID 136110485, compound

HRID 566367Notes

Reaction equation

HRID 566367 reaction equation
[NH2:1][C:2]1[N:6]([CH:7]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH2:8][CH2:9][CH3:10])[N:5]=[C:4]([CH2:17][CH2:18][CH3:19])[C:3]=1[C:20]([NH2:22])=[O:21].[CH3:23][O:24][C:25]1[CH:26]=[C:27]([CH2:33][C:34](OC)=O)[CH:28]=[CH:29][C:30]=1[O:31][CH3:32].CC(C)([O-])C.[K+].C(=O)([O-])O.[Na+]>ClCCl>[CH3:23][O:24][C:25]1[CH:26]=[C:27]([CH:28]=[CH:29][C:30]=1[O:31][CH3:32])[CH2:33][C:34]1[NH:22][C:20](=[O:21])[C:3]2[C:4]([CH2:17][CH2:18][CH3:19])=[N:5][N:6]([CH:7]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH2:8][CH2:9][CH3:10])[C:2]=2[N:1]=1

Participants

6

Reactant 4

HCID 85213Benzeneacetic acid, 3,4-dimethoxy-, methyl esterHCID 516892Sodium BicarbonateHCID 23665647Potassium tert-butoxideHCID 59932330HCID 59932330, compound

Product 1

HCID 136110485HCID 136110485, compoundYield 74.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6 mg (0.019 mmol) of 5-amino-3-propyl-1-(4-decyl)-1H-pyrazole-4-carboxamide and 20 mg (0.095 mmol) of methyl 3,4-dimethoxyphenylacetate are refluxed for 6 hours in 0.3 ml of a 0.5M ethanolic potassium tert-butoxide solution. After dichloromethane and saturated aqueous sodium hydrogen carbonate have been added, the phases are separated. Purification by chromatography gives 6.6 mg (68%) of a solid, Rf=0.25 (dichloromethane/methanol=15:1).

Workup

  1. customthe phases are separated
  2. customPurification by chromatography

Sources & evidence

ORD record
ord-29e87a93cc2749da8f5202092b726f94
Source dataset
uspto-grants-2001_01
Patent number
US06174884B1

Reaction notes

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