Hydrochloric Acid → 1-(1-hydroxy-2-piperidin-4-ylethyl)-2-phenyl-2,5-dihydro-4H-pyrazolo[3,4-c]quinolin-4-one

HRID 1095352Notes

Reaction equation

HRID 1095352 reaction equation
[OH:1][CH:2]([C:17]1[N:18]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[N:19]=[C:20]2[C:29]=1[C:28]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[NH:22][C:21]2=[O:30])[CH2:3][CH:4]1[CH2:9][CH2:8][N:7](C(OC(C)(C)C)=O)[CH2:6][CH2:5]1.Cl.[OH-].[Na+]>C(#N)C>[OH:1][CH:2]([C:17]1[N:18]([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[N:19]=[C:20]2[C:29]=1[C:28]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[NH:22][C:21]2=[O:30])[CH2:3][CH:4]1[CH2:9][CH2:8][NH:7][CH2:6][CH2:5]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 57446217HCID 57446217, compound

Product 1

HCID 574462181-(1-hydroxy-2-piperidin-4-ylethyl)-2-phenyl-2,5-dihydro-4H-pyrazolo[3,4-c]quinolin-4-oneYield 51.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Tert-butyl 4-[2-hydroxy-2-(4-oxo-2-phenyl-4,5-dihydro-2H-pyrazolo[3,4-c]quinolin-1-yl)ethyl]piperidine-1-carboxylate (100 mg, 0.2 mmol) was combined with concentrated hydrochloric acid (1 mL) and stirred at ambient temperature for 30 min. The reaction was poured over ice and the pH of the ice slurry was brought to 12 with 50% aqueous sodium hydroxide. The aqueous layer was extracted with dichloromethane. The combined organic extracts were dried over sodium sulfate, filtered, and concentrated under reduced pressure. The resulting material was purified by automated flash chromatography (AnaLogix, eluted with a gradient of 0-60% CMA in chloroform) to provide an oily solid. The oily solid was stirred in acetonitrile. A solid was isolated by filtration to provide 40 mg of 1-(1-hydroxy-2-piperidin-4-ylethyl)-2-phenyl-2,5-dihydro-4H-pyrazolo[3,4-c]quinolin-4-one as a tan powder, mp 258-261° C. MS (APCI) m/z 389 (M+H)+; Anal. calcd for C23H24N4O2.0.6H2O: C, 69.19; H, 6.36; N, 14.03. Found: C, 69.02; H, 6.23; N, 14.11.

Workup

  1. additionThe reaction was poured over ice
  2. extractionThe aqueous layer was extracted with dichloromethane
  3. dry with materialThe combined organic extracts were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting material was purified by automated flash chromatography (AnaLogix
  7. washeluted with a gradient of 0-60% CMA in chloroform)
  8. customto provide an oily solid
  9. customA solid was isolated by filtration

Sources & evidence

ORD record
ord-5b1cc39b268e44a9844edcc73fd11f7a
Source dataset
uspto-grants-2012_03
Patent number
US08138173B2

Reaction notes

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