Potassium Iodide → HCID 135599942, compound

HRID 1175818Notes

Reaction equation

HRID 1175818 reaction equation
[NH2:1][C:2]1[N:3]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH3:24])[CH:18]=2)[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[CH2:27][CH2:28][N:29]1[CH2:34][CH2:33][O:32][CH2:31][CH2:30]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:22]=[CH:21][CH:20]=[C:19]([O:23][CH3:24])[CH:18]=2)[N:4]=[C:5]2[C:14]3[CH:13]=[CH:12][C:11]([O:15][CH2:27][CH2:28][N:29]4[CH2:34][CH2:33][O:32][CH2:31][CH2:30]4)=[CH:10][C:9]=3[NH:8][C:7](=[O:16])[C:6]=12

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 77210Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)HCID 178490898HCID 178490898, compound

Product 1

HCID 135599942HCID 135599942, compoundYield 36%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 3-amino-2-(3-methoxyphenyl)-7-hydroxy-2,5-dihydro-4H-pyrazolo[4,3-c]quinolin-4-one (150 mg), 4-(2-chloroethyl)morpholine hydrochloride (109 mg), potassium carbonate (163 mg), potassium iodide (5 mg) and N,N-dimethylformamide (5 mg) was stirred at 80° C. for 3 hours. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The extract was washed with water and brine, dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified with silica gel column chromatography. To the concentrated residue of fraction was added ethyl acetate. The precipitated solid was collected by filtration, washed with ethyl acetate, and dried to obtain the target compound (73 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue was purified with silica gel column chromatography
  6. additionTo the concentrated residue of fraction was added ethyl acetate
  7. filtrationThe precipitated solid was collected by filtration
  8. washwashed with ethyl acetate
  9. customdried

Sources & evidence

ORD record
ord-af47d44335064c8a8fe0aede38290ace
Source dataset
uspto-grants-2010_11
Patent number
US07842701B2

Reaction notes

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