Ethyl 2-(3-formylphenoxy)acetate → HCID 178472964, compound

HRID 1597858Notes

Reaction equation

HRID 1597858 reaction equation
[CH:1]1([N:6]2[C:10]([NH2:11])=[C:9]([C:12]([NH2:14])=[O:13])[C:8]([CH2:15][CH3:16])=[N:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:17]([O:19][C:20]([CH2:22][O:23][C:24]1[CH:25]=[C:26]([CH:29]=[CH:30][CH:31]=1)[CH:27]=O)=[O:21])[CH3:18]>>[CH:1]1([N:6]2[C:10]3=[N:11][C:27]([C:26]4[CH:29]=[CH:30][CH:31]=[C:24]([O:23][CH2:22][C:20]([O:19][CH2:17][CH3:18])=[O:21])[CH:25]=4)=[N:14][C:12](=[O:13])[C:9]3=[C:8]([CH2:15][CH3:16])[NH:7]2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

3

Reactant 2

HCID 1494377Ethyl 2-(3-formylphenoxy)acetateHCID 224493525-amino-1-cyclopentyl-3-ethyl-1H-pyrazole-4-carboxamide

Product 1

HCID 178472964HCID 178472964, compoundYield 37.9%

Conditions

Temperature
160 °C

Procedure

A mixture of 1-cyclopentyl-3-ethyl-5-amino-1H-pyrazole-4-carboxamide (3.54 g, 15.95 mmol), 3-(ethoxycarbonylmethoxy) benzaldehyde (4.3 g) and xylenes (20 ml) was heated at 160° C. overnight. The reaction mixture was cooled to room temperature, a solid formed which was collected by filtration and washed with methanol and then ether. The product was recrystallized from acetonitrile to afford 2.48 g of 1-cyclopentyl-3-ethyl-6-[3-(ethoxycarbonylmethoxy)phenyl]pyrazolo[3,4-d]pyrimidin-4-one. An additional 0.3 g of product was also obtained from the recrystallization of the filtrate for a total of 2.78 g.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customa solid formed which
  3. filtrationwas collected by filtration
  4. washwashed with methanol
  5. customThe product was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-a6c8c7c76d2142eca150bb11780362e4
Source dataset
uspto-grants-1998_04
Patent number
US05736548

Reaction notes

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