Hydrochloric Acid → HCID 178437869, compound

HRID 1600811Notes

Reaction equation

HRID 1600811 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.[F:18][C:19]([F:33])([F:32])[C:20]1[CH:25]=[CH:24][C:23]([CH2:26][C:27](OCC)=O)=[CH:22][CH:21]=1.Cl>C(O)C.O>[CH:2]1([N:7]2[C:11]3=[N:12][C:27]([CH2:26][C:23]4[CH:22]=[CH:21][C:20]([C:19]([F:18])([F:32])[F:33])=[CH:25][CH:24]=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 5360545SodiumHCID 14134124Ethyl (4-(trifluoromethyl)phenyl)acetateHCID 224493525-amino-1-cyclopentyl-3-ethyl-1H-pyrazole-4-carboxamide

Product 1

HCID 178437869HCID 178437869, compoundYield 57.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Sodium (622 mg) was dissolved in ethanol (45 mL) and then 1-cyclopentyl-3-ethyl-5-amino-1H-pyrazole-4-carboxamide (3.0 g, 13.5 mmol), followed by ethyl 4-trifluoromethylphenylacetate (6.27 g, 27 mmol) were added. The reaction mixture was refluxed overnight, cooled to room temperature, and the solvent was stripped. Water, followed by 2N HCl were added to the residue and the product was collected by filtration, recrystallized from ether and dried at 110° C. and 0.2 mm Hg to afford 3.03 g of 1-cyclopentyl-3-ethyl-6-(4-trifluoromethylphenylmethyl)pyrazolo[3,4-d]pyrimidin-4-one, m.p. 212-213° 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. customrecrystallized from ether
  6. customdried at 110° C.

Sources & evidence

ORD record
ord-aecf132789cb46b39c61f67741bb4186
Source dataset
uspto-grants-1999_11
Patent number
US05977118

Reaction notes

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