Sodium → HCID 178437878, compound

HRID 1600797Notes

Reaction equation

HRID 1600797 reaction equation
[Na].[CH:2]1([N:7]2[C:11]([NH2:12])=[C:10]([C:13]([NH2:15])=[O:14])[C:9]([CH2:16][CH3:17])=[N:8]2)[CH2:6][CH2:5][CH2:4][CH2:3]1.[NH:18]1[C:22]([CH2:23][O:24][C:25]2[CH:30]=[CH:29][C:28]([CH2:31][C:32](OC)=O)=[CH:27][CH:26]=2)=[N:21][N:20]=[N:19]1>C(O)C>[CH:2]1([N:7]2[C:11]3=[N:12][C:32]([CH2:31][C:28]4[CH:27]=[CH:26][C:25]([O:24][CH2:23][C:22]5[NH:18][N:19]=[N:20][N:21]=5)=[CH:30][CH:29]=4)=[N:15][C:13](=[O:14])[C:10]3=[C:9]([CH2:16][CH3:17])[NH:8]2)[CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 5360545SodiumHCID 224493525-amino-1-cyclopentyl-3-ethyl-1H-pyrazole-4-carboxamideHCID 178499470HCID 178499470, compound

Product 1

HCID 178437878HCID 178437878, compoundYield 13.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium (0.253 g) was dissolved in ethanol (15 ml) and then 1-cyclopentyl-3-ethyl-5-amino-1H-pyrazole-4-carboxamide (0.813 g, 3.7 mmol) and methyl 4-(5-tetrazolylmethoxy)phenylacetate (17 g, 7.3 mmol) were added. The reaction mixture was refluxed for about 2 days, cooled, and then the solvent was removed in vacuo. The residue was treated with water and acetic acid and the precipitate which formed was collected by filtration and dried at 60° C. under vacuum. The product was then dissolved in ethyl acetate, extracted with Na2CO3 (4×200 ml) and the aqueous layer was acidified to pH 2.5 with concentrated HCl. The aqueous layer was then extracted with ethyl acetate (2×300 ml) and the organic layer was dried over MgSO4, filtered and concentrated in vacuo. The solid residue was recrystallized from ethyl acetate to afford 0.21 g of 1-cyclopentyl-3-ethyl-6-[4-(5-tetrazolylmethoxy)phenylmethyl]pyrazolo[3,4-d]pyrimidin-4-one.2/5 hydrate, m.p. 240-242° C.

Workup

  1. temperatureThe reaction mixture was refluxed for about 2 days
  2. temperaturecooled
  3. customthe solvent was removed in vacuo
  4. additionThe residue was treated with water and acetic acid
  5. customthe precipitate which formed
  6. filtrationwas collected by filtration
  7. customdried at 60° C. under vacuum
  8. dissolutionThe product was then dissolved in ethyl acetate
  9. extractionextracted with Na2CO3 (4×200 ml)
  10. extractionThe aqueous layer was then extracted with ethyl acetate (2×300 ml)
  11. dry with materialthe organic layer was dried over MgSO4
  12. filtrationfiltered
  13. concentrationconcentrated in vacuo
  14. customThe solid residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-5412de8b039743f8ab0e544f760628f9
Source dataset
uspto-grants-1999_11
Patent number
US05977118

Reaction notes

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