Potassium Hydroxide → HCID 23442314, compound

HRID 2119642Notes

Reaction equation

HRID 2119642 reaction equation
[CH3:1][N:2]1[C:14]2[C:13](=[O:15])[C:12]3[CH:11]=[C:10]([CH2:16][C:17]4[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=4)[C:20]#[N:21])[CH:9]=[CH:8][C:7]=3[NH:6][C:5]=2[CH:4]=[N:3]1.[OH-:25].[K+].[Cl-].[NH4+]>CC(O)(C)C.CS(C)=O>[CH3:1][N:2]1[C:14]2[C:13](=[O:15])[C:12]3[CH:11]=[C:10]([CH2:16][C:17]4[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=4)[C:20]([NH2:21])=[O:25])[CH:9]=[CH:8][C:7]=3[NH:6][C:5]=2[CH:4]=[N:3]1

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 25517Ammonium ChlorideHCID 23442326HCID 23442326, compound

Product 1

HCID 23442314HCID 23442314, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6386tert-ButanolSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of 3-[(1-methyl-9-oxo-4,9-dihydro-1H-pyrazolo[4,3-b]quinolin-7-yl)methyl]benzonitrile (EXAMPLE 28, step 2, 100 mg, 0.32 mmol) and powdered potassium hydroxide (89 mg, 1.59 mmol) in 2-methyl-2-propanol (5 ml) and dimethylsulfoxide (2 ml) was stirred at 65° C. for 4.5 h. After cooling to room temperature, the mixture was poured into saturated aqueous ammonium chloride (50 ml), and the precipitate was collected by filtration. This yellow powder was washed with water, methanol and dichloromethane to give 55 mg (52%) of the title compound as a yellow solid.

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationthe precipitate was collected by filtration
  3. washThis yellow powder was washed with water, methanol and dichloromethane

Sources & evidence

ORD record
ord-2b2a564337d24e94b85969bfa4f9c5eb
Source dataset
uspto-grants-2004_02
Patent number
US06686373B2

Reaction notes

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