Acetic Acid → HCID 178437902, compound

HRID 1860570Notes

Reaction equation

HRID 1860570 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([C:14]([O:16]CC)=[O:15])=[CH:9][C:8]=2[Cl:19])[N:5]=[C:4]([CH2:20][CH3:21])[C:3]=1[C:22]([NH2:24])=[O:23].[CH3:25][O:26][C:27]1[CH:32]=[CH:31][C:30]([CH2:33][C:34](OC)=O)=[CH:29][CH:28]=1.[O-]CC.[Na+].CC(O)=O>C(O)C>[Cl:13][C:12]1[CH:11]=[C:10]([C:14]([OH:16])=[O:15])[CH:9]=[C:8]([Cl:19])[C:7]=1[N:6]1[C:2]2=[N:1][C:34]([CH2:33][C:30]3[CH:31]=[CH:32][C:27]([O:26][CH3:25])=[CH:28][CH:29]=3)=[N:24][C:22](=[O:23])[C:3]2=[C:4]([CH2:20][CH3:21])[NH:5]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 90266Methyl 4-methoxyphenylacetateHCID 2723922Sodium ethoxideHCID 18540687HCID 18540687, compound

Product 1

HCID 178437902HCID 178437902, compoundYield 75.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Part D: To a stirred solution of 500 mg (1.35 mmol) of 5-amino-3-ethyl-1-(2,6-dichloro-4-carboethoxyphenyl)pyrazole-4-carboxamide in 10 mL ethanol was added 1.45 g (8.1 mmol) of methyl 4-methoxyphenylacetate followed by 2.6 mL (8.1 mmol) of 2.66 M sodium ethoxide in ethanol. The reaction was heated at relux for 18 h and then 10% aq. HOAc was added. After stirring an additional hour at relux, the heat was removed and the reaction solution was poured into ice water, stirred 10 min. and filtered. The solid was washed with water and diethyl ether and dried to give 480 mg (75%) of 1-(2,6-dichloro-4-carboxyphenyl)-3-ethyl-6-(4-methoxybenzyl)pyrazolo[3,4-d]pyrimidin-4-one, mp 277° C. Mass Spec.: (ES−) 471 (M−H)−.

Workup

  1. temperatureThe reaction was heated at relux for 18 h
  2. customthe heat was removed
  3. additionthe reaction solution was poured into ice water
  4. stirringstirred 10 min.
  5. filtrationfiltered
  6. washThe solid was washed with water and diethyl ether
  7. customdried

Sources & evidence

ORD record
ord-9ba200c9d2fe4ca28645554f413bf6f4
Source dataset
uspto-grants-2003_03
Patent number
US06531477B1

Reaction notes

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