Sodium Carbonate → HCID 57446232, compound

HRID 1095366Notes

Reaction equation

HRID 1095366 reaction equation
[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]3Cl)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-:37].[Na+].[Na+]>Cl>[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[NH:21][C:20]3=[O:37])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 57446231HCID 57446231, compound

Product 1

HCID 57446232HCID 57446232, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

1-[2-(4-Benzylpiperazin-1-yl)ethyl]-4-chloro-2-phenyl-2H-pyrazolo[3,4-c]quinoline (0.32 g, 0.66 mmol) was refluxed in 5 mL of 6 N aqueous hydrochloric acid for 1 hour. The mixture was allowed to cool to ambient temperature, and the pH was adjusted to 10 with 10% w/v aqueous sodium carbonate. This mixture was concentrated under reduced pressure, and the residue was purified by automated flash chromatography eluting with a gradient of 0-15% CMA in chloroform. The residue was triturated with acetonitrile, isolated by filtration, and dried to afford 0.050 g of 1-[2-(4-benzylpiperazin-1-yl)ethyl]-2-phenyl-2,5-dihydro-4H-pyrazolo[3,4-c]quinolin-4-one as off-white needles, mp 211-212.5° C. MS (ESI) m/z 464 (M+H)+; Anal. calcd for C29H29N5O: C, 75.14; H, 6.31; N, 15.11. Found: C, 74.84; H, 6.35; N, 15.04.

Workup

  1. concentrationThis mixture was concentrated under reduced pressure
  2. customthe residue was purified by automated flash chromatography
  3. washeluting with a gradient of 0-15% CMA in chloroform
  4. customThe residue was triturated with acetonitrile
  5. customisolated by filtration
  6. customdried

Sources & evidence

ORD record
ord-dcc0862bb14841b1a29bf4e310a64845
Source dataset
uspto-grants-2012_03
Patent number
US08138173B2

Reaction notes

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