Potassium Iodide → 3-amino-2-(3-hydroxyphenyl)-7-[3-(4-methyl-1-piperazinyl)propoxy]-2,5-dihydro-4H-pyrazolo[4,3-c]quinolin-4-one

HRID 1175807Notes

Reaction equation

HRID 1175807 reaction equation
[NH2:1][C:2]1[N:3]([C:17]2[CH:22]=[C:21]([O:23]C)[CH:20]=[CH:19][C:18]=2Cl)[N:4]=[C:5]2[C:14]3[CH:13]=[CH:12][C:11]([OH:15])=[CH:10][C:9]=3[NH:8][C:7](=[O:16])[C:6]=12.Cl.Cl.Cl[CH2:29][CH2:30][CH2:31][N:32]1[CH2:37][CH2:36][N:35]([CH3:38])[CH2:34][CH2:33]1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>O.CN(C)C=O>[NH2:1][C:2]1[N:3]([C:17]2[CH:18]=[CH:19][CH:20]=[C:21]([OH:23])[CH:22]=2)[N:4]=[C:5]2[C:14]3[CH:13]=[CH:12][C:11]([O:15][CH2:29][CH2:30][CH2:31][N:32]4[CH2:37][CH2:36][N:35]([CH3:38])[CH2:34][CH2:33]4)=[CH:10][C:9]=3[NH:8][C:7](=[O:16])[C:6]=12

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 30140681-(3-Chloropropyl)-4-methylpiperazine dihydrochlorideHCID 178490735HCID 178490735, compound

Product 1

HCID 1355998973-amino-2-(3-hydroxyphenyl)-7-[3-(4-methyl-1-piperazinyl)propoxy]-2,5-dihydro-4H-pyrazolo[4,3-c]quinolin-4-oneYield 13.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 3-amino-2-(2-chloro-5-methoxyphenyl)-7-hydroxy-2,5-dihydro-4H-pyrazolo[4,3-c]quinolin-4-one (75 mg), 1-(3-chloropropyl)-4-methylpiperazine dihydrochloride (70 mg), potassium carbonate (112 mg), potassium iodide (5 mg) and N,N-dimethylformamide (3 ml) was stirred at 80° C. for 4 hours. To the reaction mixture was added water, extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure. To the concentrated residue (53 mg) was added DL-methilonine (265 mg) and methanesulfonic acid (3 ml), and the mixture was stirred at 90° C. for one night. The reaction mixture was cooled and then pH of the reaction mixture was adjusted to about 9 by adding an aqueous 20% sodium hydroxide and 5% sodium hydrogen carbonate, and extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous sodium sulfate and the solvent was distilled off under reduced pressure. The residue was purified with propylaminated silica gel column chromatography to obtain the target compound (13 mg).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. additionTo the concentrated residue (53 mg) was added DL-methilonine (265 mg) and methanesulfonic acid (3 ml)
  6. stirringthe mixture was stirred at 90° C. for one night
  7. temperatureThe reaction mixture was cooled
  8. additionby adding an aqueous 20% sodium hydroxide and 5% sodium hydrogen carbonate
  9. extractionextracted with ethyl acetate
  10. washThe extract was washed with brine
  11. dry with materialdried over anhydrous sodium sulfate
  12. distillationthe solvent was distilled off under reduced pressure
  13. customThe residue was purified with propylaminated silica gel column chromatography

Sources & evidence

ORD record
ord-342e9001d1a14468960fc69b450d14a2
Source dataset
uspto-grants-2010_11
Patent number
US07842701B2

Reaction notes

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