Benzeneacetic acid, 3,4-dimethoxy-, methyl ester → HCID 136132171, compound

HRID 566361Notes

Reaction equation

HRID 566361 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][CH3:18])[C:3]=1[C:19]([NH2:21])=[O:20].[CH3:22][O:23][C:24]1[CH:25]=[C:26]([CH2:32][C:33](OC)=O)[CH:27]=[CH:28][C:29]=1[O:30][CH3:31].CC(C)([O-])C.[K+].C(=O)([O-])O.[Na+]>ClCCl>[CH3:22][O:23][C:24]1[CH:25]=[C:26]([CH:27]=[CH:28][C:29]=1[O:30][CH3:31])[CH2:32][C:33]1[NH:21][C:19](=[O:20])[C:3]2[C:4]([CH2:17][CH3:18])=[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 59932338HCID 59932338, compound

Product 1

HCID 136132171HCID 136132171, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6 mg (0.02 mmol) of 5-amino-3-ethyl-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 4 mg (42%) of a solid, Rf=0.47 (dichloromethane/methanol=15:1).

Workup

  1. customthe phases are separated
  2. customPurification by chromatography

Sources & evidence

ORD record
ord-0b0d127aaed54c2e8c63f75c58b73dbe
Source dataset
uspto-grants-2001_01
Patent number
US06174884B1

Reaction notes

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