Hydrochloric Acid → HCID 178437883, compound

HRID 1600816Notes

Reaction equation

HRID 1600816 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.[S:18]1[CH:22]=[CH:21][CH:20]=[C:19]1[CH2:23][C:24](OCC)=O.Cl>C(O)C.O>[CH:2]1([N:7]2[C:11]3=[N:12][C:24]([CH2:23][C:19]4[S:18][CH:22]=[CH:21][CH:20]=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

7

Reactant 4

HCID 313Hydrochloric AcidHCID 93657Ethyl 2-thienylacetateHCID 5360545SodiumHCID 224493525-amino-1-cyclopentyl-3-ethyl-1H-pyrazole-4-carboxamide

Product 1

HCID 178437883HCID 178437883, compoundYield 40.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

Sodium (414 mg) was dissolved in ethanol (45 ml) and then 1-cyclopentyl-3-ethyl-5-amino-1H-pyrazole-4-carboxamide (2 g, 9 mmol), followed by ethyl 2-thienylacetate (3.1 g, 18 mmol) were added. The reaction mixture was refluxed overnight, cooled to room temperature and the ethanol was stripped. Water, followed by 2N HCl were added to the residue and the product was collected by filtration, and washed with water. The product was recrystallized from ethyl acetate and dried at 90° C. and 0.2 mm Hg to afford 1.19 g of 1-cyclopentyl-3-ethyl-6-(2-thienylmethyl)pyrazolo[3,4-d]pyrimidin-4-one, m.p. 173-174° C.

Workup

  1. additionwere added
  2. temperatureThe reaction mixture was refluxed overnight
  3. additionwere added to the residue
  4. filtrationthe product was collected by filtration
  5. washwashed with water
  6. customThe product was recrystallized from ethyl acetate
  7. customdried at 90° C.

Sources & evidence

ORD record
ord-8914c3c579374ac4bc4f3cf7eee7e694
Source dataset
uspto-grants-1999_11
Patent number
US05977118

Reaction notes

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