Acetic Acid → HCID 178437902, compound

HRID 411590Notes

Reaction equation

HRID 411590 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.[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 5360545SodiumHCID 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 ehtoxide 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-84741d508e664a0e8b53efc98f982296
Source dataset
uspto-grants-2003_05
Patent number
US06559152B2

Reaction notes

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