Ethyl 3-pyridylacetate → HCID 178437874, compound

HRID 1600800Notes

Reaction equation

HRID 1600800 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.[N:18]1[CH:23]=[CH:22][CH:21]=[C:20]([CH2:24][C:25](OCC)=O)[CH:19]=1.N1C=CC=C(CC([O-])=O)C=1>C(O)C.O.C(O)(=O)C>[CH:2]1([N:7]2[C:11]3=[N:12][C:25]([CH2:24][C:20]4[CH:19]=[N:18][CH:23]=[CH:22][CH:21]=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

8

Reactant 4

HCID 96490Ethyl 3-pyridylacetateHCID 4615299(Pyridin-3-yl)acetateHCID 5360545SodiumHCID 224493525-amino-1-cyclopentyl-3-ethyl-1H-pyrazole-4-carboxamide

Product 1

HCID 178437874HCID 178437874, compoundYield 56%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

Sodium (0.11 g) was dissolved in ethanol and then 1-cyclopentyl-3-ethyl-5-amino-1H-pyrazole-4-carboxamide (0.49 g, 2.21 mmol) was added, followed 10 minutes later by ethyl 3-pyridinylacetate (0.73 g) in ethanol (2 mL) . The reaction mixture was refluxed overnight, additional 3-pyridinylacetate (0.35 g) was added and the reaction mixture was again refluxed overnight. The reaction mixture was cooled to room temperature, the solvent was stripped and the residue was dissolved in water and treated with acetic acid (to pH of 7). The mixture was extracted with CHCl3 (3×50 mL), the organic layers were combined, dried over MgSO4 and stripped to a pale yellow oil. The oil was crystallized by the addition of ether and the product was collected by filtration and washed with ether to afford 0.4 g of 1-cyclopentyl-3-ethyl-6-[3-pyridinylmethyl]pyrazolo[3,4-d]pyrimidin-4-one.

Workup

  1. temperatureThe reaction mixture was refluxed overnight
  2. extractionThe mixture was extracted with CHCl3 (3×50 mL)
  3. dry with materialdried over MgSO4
  4. customThe oil was crystallized by the addition of ether
  5. filtrationthe product was collected by filtration
  6. washwashed with ether

Sources & evidence

ORD record
ord-495b338068a04cfa84ec6aa9e493e4ce
Source dataset
uspto-grants-1999_11
Patent number
US05977118

Reaction notes

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