HCID 21846110, compound → HCID 178437844, compound

HRID 619194Notes

Reaction equation

HRID 619194 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.[N:17]1[CH:22]=[CH:21][C:20]([CH2:23][O:24][C:25]2[CH:26]=[C:27]([CH:30]=[CH:31][CH:32]=2)[CH:28]=O)=[CH:19][CH:18]=1>[Pd]>[CH:1]1([N:6]2[C:10]3=[N:11][C:28]([C:27]4[CH:30]=[CH:31][CH:32]=[C:25]([O:24][CH2:23][C:20]5[CH:19]=[CH:18][N:17]=[CH:22][CH:21]=5)[CH:26]=4)=[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

4

Reactant 2

HCID 21846110HCID 21846110, compoundHCID 224493525-amino-1-cyclopentyl-3-ethyl-1H-pyrazole-4-carboxamide

Product 1

HCID 178437844HCID 178437844, compoundYield 21.6%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A mixture of 1-cyclopentyl-3-ethyl-5-amino-1H-pyrazole-4-carboxamide (2.7 g, 0.124 mol), 3-(4-pyridinylmethoxy)benzaldehyde (3.95 g, 0.0185 mol) and xylenes (100 ml) was refluxed overnight. Additional carboxamide (1 g) was added and the mixture was refluxed for another 2 days. 10% palladium on carbon (1 g) was added and the mixture was refluxed for another 3 hours. The catalyst was removed by filtration, the filtrate was concentrated in vacuo and the solid residue was collected by filtration. Additional product was obtained by concentration of the mother liquors and the combined product fractions were recrystallized from ethyl acetate to afford 1.66 g of 1-cyclopentyl-3-ethyl-6-[3-[4-pyridinylmethoxy]phenyl]pyrazolo[3,4-d]pyrimidin-4-one, m.p. 230-232° C.

Workup

  1. temperaturewas refluxed overnight
  2. temperaturethe mixture was refluxed for another 2 days
  3. temperaturethe mixture was refluxed for another 3 hours
  4. customThe catalyst was removed by filtration
  5. concentrationthe filtrate was concentrated in vacuo
  6. filtrationthe solid residue was collected by filtration
  7. customAdditional product was obtained by concentration of the mother liquors
  8. customthe combined product fractions were recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-681266ed57cc43b5b8d652683a540da4
Source dataset
uspto-grants-1999_09
Patent number
US05958929

Reaction notes

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