Water → HCID 57446231, compound

HRID 1095365Notes

Reaction equation

HRID 1095365 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([C:14](=O)[CH2:15][C:16]2[N:17]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[N:18]=[C:19]3[C:28]=2[C:27]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[N:21]=[C:20]3[Cl:29])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][C:16]2[N:17]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[N:18]=[C:19]3[C:28]=2[C:27]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[N:21]=[C:20]3[Cl:29])[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydride2×HCID 57446230HCID 57446230, compound

Product 1

HCID 57446231HCID 57446231, compoundYield 15.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

1-[2-(4-Benzylpiperazin-1-yl)-2-oxoethyl]-4-chloro-2-phenyl-2H-pyrazolo[3,4-c]quinoline (3.05 g, 6.1 mmol) was dissolved in 90 mL of tetrahydrofuran and cooled to 0° C. Lithium aluminum hydride (0.41 g, 10.75 mmol) was added. The mixture was allowed to stir at ambient temperature for 48 hours. A second portion of lithium aluminum hydride (0.17 g, 4.5 mmol) was added, and the mixture was stirred for 24 hours at ambient temperature. 0.6 mL of water, followed by 0.6 mL of 2 N aqueous sodium hydroxide and 1.8 mL of water was added. After stirring at ambient temperature for 30 minutes, the mixture was dried over magnesium sulfate, filtered through a layer of CELITE filter aid, and concentrated under reduced pressure. The residue was purified by automated flash chromatography eluting with a gradient of 4-18% CMA in chloroform, followed by automated flash chromatography eluting with a gradient of 10-67% ethyl acetate in hexanes to provide 0.46 g of 1-[2-(4-benzylpiperazin-1-yl)ethyl]-4-chloro-2-phenyl-2H-pyrazolo[3,4-c]quinoline as a yellow solid, mp 75-77° C. MS (ESI) m/z 482 (M+H)+; Anal. calcd for C29H28ClN5: C, 72.26; H, 5.85; N, 14.53. Found: C, 72.00; H, 5.67; N, 14.37.

Workup

  1. stirringthe mixture was stirred for 24 hours at ambient temperature
  2. additionwas added
  3. stirringAfter stirring at ambient temperature for 30 minutes
  4. dry with materialthe mixture was dried over magnesium sulfate
  5. filtrationfiltered through a layer of CELITE
  6. filtrationfilter aid
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by automated flash chromatography
  9. washeluting with a gradient of 4-18% CMA in chloroform
  10. washeluting with a gradient of 10-67% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-ce583a35613247c59343659361d3c62f
Source dataset
uspto-grants-2012_03
Patent number
US08138173B2

Reaction notes

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