Water → 7-(2-methoxy-4,6-dimethylpyridin-3-yl)-1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazolo[4,3-c]quinolin-4(5H)-one

HRID 1043937Notes

Reaction equation

HRID 1043937 reaction equation
F[C:2]1[CH:7]=[C:6]([C:8]2[C:9]([O:16][CH3:17])=[N:10][C:11]([CH3:15])=[CH:12][C:13]=2[CH3:14])[CH:5]=[CH:4][C:3]=1[C:18]1[N:22]([CH:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)[N:21]=[CH:20][C:19]=1[C:29]([NH2:31])=[O:30].O>CN1C(=O)CCC1>[CH3:17][O:16][C:9]1[C:8]([C:6]2[CH:7]=[CH:2][C:3]3[C:18]4[N:22]([CH:23]5[CH2:28][CH2:27][O:26][CH2:25][CH2:24]5)[N:21]=[CH:20][C:19]=4[C:29](=[O:30])[NH:31][C:4]=3[CH:5]=2)=[C:13]([CH3:14])[CH:12]=[C:11]([CH3:15])[N:10]=1

Participants

4

Reactant 2

HCID 962WaterHCID 866863655-[2-fluoro-4-(2-methoxy-4,6-dimethylpyridin-3-yl)phenyl]-(tetrahydro-2H-pyran-4-yl)-1H-pyrazole-4-carboxamide

Product 1

HCID 1362539837-(2-methoxy-4,6-dimethylpyridin-3-yl)-1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazolo[4,3-c]quinolin-4(5H)-oneYield 60.2%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
90 °C

Procedure

KTB (655 mg) was added to a solution of 5-[2-fluoro-4-(2-methoxy-4,6-dimethylpyridin-3-yl)phenyl]-(tetrahydro-2H-pyran-4-yl)-1H-pyrazole-4-carboxamide (1.52 g) in NMP (15 mL), and the mixture was stirred at 90° C. for 30 minutes. KTB (40 mg) was added to the reaction mixture, and the mixture was stirred at 90° C. for 30 minutes. Further, KTB (40 mg) was added to the reaction mixture, and the mixture was stirred at 90° C. for 30 minutes. The reaction mixture was cooled to room temperature. Water (3 mL) was added to the reaction mixture. The solid was precipitated. After stirring for one hour directly, the precipitated solid was collected by filtration. The residue was washed with water (1 mL). The resulting solid was suspended in 1-propanol/water (9/1) (2 mL) and dissolved by heating under reflux. The solution was cooled to room temperature over one hour. The precipitated solid was collected by filtration. The resulting solid was dried under reduced pressure at 50° C. to give the title compound (872 mg). The instrumental data were identical to those of the title compound synthesized in Example 4.

Workup

  1. additionKTB (40 mg) was added to the reaction mixture
  2. stirringthe mixture was stirred at 90° C. for 30 minutes
  3. additionFurther, KTB (40 mg) was added to the reaction mixture
  4. stirringthe mixture was stirred at 90° C. for 30 minutes
  5. temperatureThe reaction mixture was cooled to room temperature
  6. customThe solid was precipitated
  7. stirringAfter stirring for one hour directly
  8. filtrationthe precipitated solid was collected by filtration
  9. washThe residue was washed with water (1 mL)
  10. dissolutiondissolved
  11. temperatureby heating
  12. temperatureunder reflux
  13. temperatureThe solution was cooled to room temperature over one hour
  14. filtrationThe precipitated solid was collected by filtration
  15. customThe resulting solid was dried under reduced pressure at 50° C.

Sources & evidence

ORD record
ord-cc5aae77424445c3a3e6cacf79e91aaf
Source dataset
uspto-grants-2013_10
Patent number
US08563565B2

Reaction notes

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