Hydrochloric Acid → HCID 178437888, compound

HRID 1600804Notes

Reaction equation

HRID 1600804 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.[C:18](OCC)(=O)[CH2:19][OH:20].Cl>C(O)C.O>[CH:2]1([N:7]2[C:11]3=[N:12][C:18]([CH2:19][OH:20])=[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

7

Reactant 4

HCID 313Hydrochloric AcidHCID 12184Ethyl GlycolateHCID 5360545SodiumHCID 224493525-amino-1-cyclopentyl-3-ethyl-1H-pyrazole-4-carboxamide

Product 1

HCID 178437888HCID 178437888, compoundYield 23.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

Sodium (0.68 g) was dissolved in ethanol and 1-cyclopentyl-3-ethyl-5-amino-1H-pyrazole-4-carboxamide (3.0 g, 13.5 mmol), followed by ethyl glycolate (2.8 g, 27 mmol) were added. The reaction mixture was refluxed overnight, the ethanol was stripped and water, followed by 2N HCl were added to the residue. A precipitate formed which was collected by filtration, washed with saturated NaHCO3, and then water. The product was recrystallized from ethyl acetate, then ether to afford 0.83 g of 1-cyclopentyl-3-ethyl-6-(hydroxymethyl)pyrazolo[3,4-d]pyrimidin-4-one, m.p. 183-184° C.

Workup

  1. additionwere added
  2. temperatureThe reaction mixture was refluxed overnight
  3. additionwere added to the residue
  4. customA precipitate formed which
  5. filtrationwas collected by filtration
  6. washwashed with saturated NaHCO3
  7. customThe product was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-881d84dad72142cba231d2466b19d599
Source dataset
uspto-grants-1999_11
Patent number
US05977118

Reaction notes

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