Methyl 2-(3,4,5-trimethoxyphenyl)acetate → HCID 135702888, compound

HRID 566340Notes

Reaction equation

HRID 566340 reaction equation
[NH2:1][C:2]1[N:6]([CH:7]([CH3:17])[CH2:8][CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:5]=[C:4]([CH2:18][CH3:19])[C:3]=1[C:20]([NH2:22])=[O:21].CC(C)([O-])C.[K+].[CH3:29][O:30][C:31]1[CH:32]=[C:33]([CH2:41][C:42](OC)=O)[CH:34]=[C:35]([O:39][CH3:40])[C:36]=1[O:37][CH3:38]>C(O)C>[CH3:40][O:39][C:35]1[CH:34]=[C:33]([CH:32]=[C:31]([O:30][CH3:29])[C:36]=1[O:37][CH3:38])[CH2:41][C:42]1[NH:22][C:20](=[O:21])[C:3]2[C:4]([CH2:18][CH3:19])=[N:5][N:6]([CH:7]([CH3:17])[CH2:8][CH2:9][CH2:10][C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:2]=2[N:1]=1

Participants

5

Reactant 3

HCID 11107458Methyl 2-(3,4,5-trimethoxyphenyl)acetateHCID 21266063HCID 21266063, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 135702888HCID 135702888, compoundYield 41.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

400 mg (1.4mmol) of 5-amino-3-ethyl-1-(1-methyl-4-phenyl-butyl)-1H-pyrazole-4-carboxamide, 750 mg (6.7 mmol) of potassium tert-butoxide and 720 mg (3.0 mmol) of methyl 3,4,5-trimethoxy-phenylacetate are refluxed for 16 hours in 10 ml of ethanol. After the solvent has been removed, the mixture is acidified with 1N HCl, extracted 3 times with dichloromethane, the organic phase is dried over sodium sulphate and the solvent is removed in vacuo. Purification by chromatography gives 286 mg (40%) of a solid, Rf=0.62 (ethyl acetate/cyclohexane=2:1).

Workup

  1. customAfter the solvent has been removed
  2. extractionextracted 3 times with dichloromethane
  3. dry with materialthe organic phase is dried over sodium sulphate
  4. customthe solvent is removed in vacuo
  5. customPurification by chromatography

Sources & evidence

ORD record
ord-96aa96c273a2492980589977139bd191
Source dataset
uspto-grants-2001_01
Patent number
US06174884B1

Reaction notes

Loading…