Acetic Acid → HCID 178437887, compound

HRID 2257032Notes

Reaction equation

HRID 2257032 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.O.[C:19](O)(=O)[CH3:20].[CH2:23](O)[CH3:24]>>[CH:2]1([N:7]2[C:11]3=[N:12][C:3]([CH2:2][N:7]4[CH2:20][CH2:19][C:23]5[C:24](=[CH:16][CH:9]=[CH:10][CH:13]=5)[CH2:11]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

6

Reactant 5

HCID 176Acetic AcidHCID 702EthanolHCID 962WaterHCID 5360545SodiumHCID 224493525-amino-1-cyclopentyl-3-ethyl-1H-pyrazole-4-carboxamide

Product 1

HCID 178437887HCID 178437887, compound

Procedure

Sodium (0.24 g) was dissolved in ethanol (25 mL) and 1-cyclopentyl-3-ethyl-5-amino-1H-pyrazole-4-carboxamide (1.09 g, 4.91 mmol) followed by ethyl 1,2,3,4-tetrahydro-2-isoquinolinyl acetate (2.15 g) were added. The reaction mixture was refluxed for about 2 days, the solvent was stripped and the residue was treated with water and acetic acid. A gum formed which was extracted with CHCl3 (3×100 mL) and the organic layers were combined, dried over MgSO4, filtered and stripped to afford a yellow solid which was washed with ether to afford (0.6 g) of crude product. The crude product was combined with the crude product from a similar experimental run and the mixture was purified by column chromatography on silica gel eluting with ethyl acetate/hexane (1/1). Additional product was also obtained from concentration of the above ether filtrate and purification by column chromatography as described above. The product fractions were pooled and recrystallized from ether to afford 1-cyclopentyl-3-ethyl-6-(1,2,3,4-tetrahydro-2-isoquinolinylmethyl)pyrazolo[3,4-d]pyrimidin-4-one, as a white solid, m.p. 149°-151° C.

Workup

  1. additionwere added
  2. temperatureThe reaction mixture was refluxed for about 2 days
  3. customA gum formed which
  4. extractionwas extracted with CHCl3 (3×100 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customto afford a yellow solid which
  8. washwas washed with ether
  9. customto afford (0.6 g) of crude product
  10. customthe mixture was purified by column chromatography on silica gel eluting with ethyl acetate/hexane (1/1)
  11. customAdditional product was also obtained from concentration of the above ether filtrate and purification by column chromatography
  12. customrecrystallized from ether

Sources & evidence

ORD record
ord-bda00c2fe9b74d819d643fd842bb0682
Source dataset
uspto-grants-1997_08
Patent number
US05656629

Reaction notes

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