Hydrochloric Acid → HCID 178437868, compound

HRID 2257043Notes

Reaction equation

HRID 2257043 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.[CH3:18][O:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[CH2:26][C:27](OC)=O.Cl>C(O)C.O>[CH:2]1([N:7]2[C:11]3=[N:12][C:27]([CH2:26][C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=4[O:19][CH3:18])=[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 99590Methyl 2-methoxybenzeneacetateHCID 5360545SodiumHCID 224493525-amino-1-cyclopentyl-3-ethyl-1H-pyrazole-4-carboxamide

Product 1

HCID 178437868HCID 178437868, compoundYield 52.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Sodium (590 mg) was dissolved in ethanol (45 mL) and then 1-cyclopentyl-3-ethyl-5-amino-1H-pyrazole-4-carboxamide (2.65 g, 12 mmol), followed by methyl 2-methoxyphenylacetate (4.7 g, 26 mmol) were added. The reaction mixture was refluxed overnight, the solvent was stripped and the residue was treated with water and then 2N HCl. The product was collected by filtration and recrystallized from ethyl acetate to afford 2.23 g of 1-cyclopentyl-3-ethyl-6-(2-methoxyphenylmethyl)pyrazolo[3,4-d]pyrimidin-4-one, m.p. 145°-146° C.

Workup

  1. additionwere added
  2. temperatureThe reaction mixture was refluxed overnight
  3. filtrationThe product was collected by filtration
  4. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-3333df153d914353b108769b4e0bb5d9
Source dataset
uspto-grants-1997_08
Patent number
US05656629

Reaction notes

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