p-Toluenesulfonic acid → HCID 178472962, compound

HRID 619152Notes

Reaction equation

HRID 619152 reaction equation
[CH:1]1([N:6]2[C:10]([NH2:11])=[C:9]([C:12]([NH2:14])=[O:13])[C:8]([CH2:15][CH3:16])=[N:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:17]([O:19][C:20]([CH2:22][O:23][C:24]1[CH:31]=[CH:30][CH:29]=[CH:28][C:25]=1[CH:26]=O)=[O:21])[CH3:18].C1(C)C=CC(S(O)(=O)=O)=CC=1>O>[CH:1]1([N:6]2[C:10]3=[N:11][C:26]([C:25]4[CH:28]=[CH:29][CH:30]=[CH:31][C:24]=4[O:23][CH2:22][C:20]([O:19][CH2:17][CH3:18])=[O:21])=[N:14][C:12](=[O:13])[C:9]3=[C:8]([CH2:15][CH3:16])[NH:7]2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 345961ethyl 2-(2-formylphenoxy)acetateHCID 224493525-amino-1-cyclopentyl-3-ethyl-1H-pyrazole-4-carboxamide

Product 1

HCID 178472962HCID 178472962, compoundYield 38.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1-cyclopentyl-3-ethyl-5-amino-1H-pyrazole-4-carboxamide (5.26 g, 23.7 mmol), 2-(ethoxycarbonylmethoxy)benzaldehyde (9.10 g, 47.3 mmol), p-toluenesulfonic acid (0.2 g) and xylenes (100 ml) was refluxed for 18 hours with the azeotropic removal of water. The solvent was removed in vacuo, and the residue was treated with ethanol and evaporated to dryness. The residue was partitioned between chloroform and 10% aqueous K2CO3, the layers were separated and the aqueous layer was extracted with chloroform (100 ml). The organic layers were combined, and concentrated to dryness. The residue was preloaded on silica gel and then was purified by column chromatography on silica gel eluting with hexanes (100%) to 20% ether/hexane to afford 3.74 g (38%) of 1-cyclopentyl-3-ethyl-6-[2-(ethoxycarbonylmethoxy)phenyl]pyrazolo[3,4-d]pyrimidin-4-one, m.p. 116-117° C.

Workup

  1. customThe solvent was removed in vacuo
  2. additionthe residue was treated with ethanol
  3. customevaporated to dryness
  4. customThe residue was partitioned between chloroform and 10% aqueous K2CO3
  5. customthe layers were separated
  6. extractionthe aqueous layer was extracted with chloroform (100 ml)
  7. concentrationconcentrated to dryness
  8. customwas purified by column chromatography on silica gel eluting with hexanes (100%) to 20% ether/hexane

Sources & evidence

ORD record
ord-29275c3232d44b87bf377e5a87ca3dfa
Source dataset
uspto-grants-1999_09
Patent number
US05958929

Reaction notes

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