1-(1-benzylpyrrolidin-3-yl)-8-{[4-(ethoxymethyl)piperidin-1-yl]carbonyl}-7-methyl-1,5-dihydro-4H-pyrazolo[4,3-c]quinolin-4-one hydrochloride → HCID 137195808, compound

HRID 69132Notes

Reaction equation

HRID 69132 reaction equation
[ClH:1].C(N1CCC([N:14]2[C:26]3[C:25]4[CH:24]=[C:23](C(N5CCC(COCC)CC5)=O)[C:22](C)=[CH:21][C:20]=4[NH:19][C:18](=[O:40])[C:17]=3[CH:16]=[N:15]2)C1)C1C=CC=CC=1>[OH-].[OH-].[Pd+2].CO>[ClH:1].[NH:14]1[C:26]2[C:25]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[NH:19][C:18](=[O:40])[C:17]=2[CH:16]=[N:15]1

Participants

4

Reactant 1

HCID 1366189621-(1-benzylpyrrolidin-3-yl)-8-{[4-(ethoxymethyl)piperidin-1-yl]carbonyl}-7-methyl-1,5-dihydro-4H-pyrazolo[4,3-c]quinolin-4-one hydrochloride

Product 1

HCID 137195808HCID 137195808, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a mixture of 224 mg of 1-(1-benzylpyrrolidin-3-yl)-8-{[4-(ethoxymethyl)piperidin-1-yl]carbonyl}-7-methyl-1,5-dihydro-4H-pyrazolo[4,3-c]quinolin-4-one hydrochloride and 9 mL of methanol was added 23 mg of a 10% palladium hydroxide/carbon powder, followed by stirring at room temperature for 20 hours under a hydrogen atmosphere of 3 atm. The insoluble material was removed by filtration, and the solvent was evaporated under reduced pressure. The residue was purified by reverse phase column chromatography (acetonitrile/water=0/100-35/65). The obtained compound was dissolved in 4 mL of methanol, and 1 mL of a 4 M hydrogen chloride-ethyl acetate solution was added thereto, followed by stirring for 1 hour. Then, the solvent was evaporated under reduced pressure and the solid was collected by filtration, washed with diethyl ether, and then dried under reduced pressure to obtain 180 mg of 8-{[4-(ethoxymethyl)piperidin-1-yl]carbonyl}-7-methyl-1-pyrrolidin-3-yl)-1,5-dihydro-4H-pyrazolo[4,3-c]quinolin-4-one hydrochloride as a white solid.

Workup

  1. customThe insoluble material was removed by filtration
  2. customthe solvent was evaporated under reduced pressure
  3. customThe residue was purified by reverse phase column chromatography (acetonitrile/water=0/100-35/65)
  4. dissolutionThe obtained compound was dissolved in 4 mL of methanol
  5. addition1 mL of a 4 M hydrogen chloride-ethyl acetate solution was added
  6. stirringby stirring for 1 hour
  7. customThen, the solvent was evaporated under reduced pressure
  8. filtrationthe solid was collected by filtration
  9. washwashed with diethyl ether
  10. customdried under reduced pressure

Sources & evidence

ORD record
ord-8a190ca20903409e9506485181c80cd2
Source dataset
uspto-grants-2014_09
Patent number
US08822448B2

Reaction notes

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