Water → HCID 23442450, compound

HRID 2119657Notes

Reaction equation

HRID 2119657 reaction equation
[CH3:1][N:2]1[C:14]2[C:13](=[O:15])[C:12]3[CH:11]=[C:10]([CH3:16])[CH:9]=[CH:8][C:7]=3[N:6]([CH2:17][C:18]#[N:19])[C:5]=2[CH:4]=[N:3]1.[OH-:20].[K+].O>CC(O)(C)C>[CH3:1][N:2]1[C:14]2[C:13](=[O:15])[C:12]3[CH:11]=[C:10]([CH3:16])[CH:9]=[CH:8][C:7]=3[N:6]([CH2:17][C:18]([NH2:19])=[O:20])[C:5]=2[CH:4]=[N:3]1

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 23442472HCID 23442472, compound

Product 1

HCID 23442450HCID 23442450, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Conditions

Temperature
85 °C

Procedure

To a solution warmed at 85° C. of (1,7-dimethyl-9-oxo-1,9-dihydro-4H-pyrazolo[4,3-b]quinolin-4-yl)acetonitrile (EXAMPLE 51, 69 mg, 0.27 mmol) in 2-methyl-2-propanol (5 ml) was added powdered potassium hydroxide (76 mg, 1.4 mmol). The mixture was stirred at 85° C. for 10 min. After cooling to ca. 40° C., the mixture was poured into water (30 ml) and extracted with ethyl acetate (30 ml×3). The combined organic layer was washed with brine (50 ml), dried over magnesium sulfate, and concentrated in vacuo. The residue was washed with diisopropyl ether and ethyl acetate to give 43 mg (59%) of the title compound as a yellow solid.

Workup

  1. temperatureAfter cooling to ca. 40° C.
  2. extractionextracted with ethyl acetate (30 ml×3)
  3. washThe combined organic layer was washed with brine (50 ml)
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. washThe residue was washed with diisopropyl ether and ethyl acetate

Sources & evidence

ORD record
ord-fb4ed0772be044789009926ed008a5a8
Source dataset
uspto-grants-2004_02
Patent number
US06686373B2

Reaction notes

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