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Water → HCID 23442443, compound

HRID 2119659
Notes
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Reaction equation

HRID 2119659 reaction equation
[CH2:1]([N:3]1[C:12]2[CH:11]=[CH:10][C:9]([CH3:13])=[CH:8][C:7]=2[C:6](=[O:14])[C:5]2[N:15]([CH3:18])[N:16]=[CH:17][C:4]1=2)[CH3:2].Cl.[CH3:20][N:21]([CH3:26])[CH2:22]CC[Cl:25].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[ClH:25].[CH3:20][N:21]([CH3:26])[CH2:22][CH2:2][CH2:1][N:3]1[C:12]2[CH:11]=[CH:10][C:9]([CH3:13])=[CH:8][C:7]=2[C:6](=[O:14])[C:5]2[N:15]([CH3:18])[N:16]=[CH:17][C:4]1=2
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 943083-(Dimethylamino)propyl chloride hydrochlorideHCID 23442433HCID 23442433, compound

Product 1

HCID 23442443HCID 23442443, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Conditions

Temperature
100 °C

Procedure

A mixture of 1,7-dimethyl-1,4-dihydro-9H-pyrazolo[4,3-b]quinolin-9-one (UK-264650) (EXAMPLE 47, step 2, 100 mg, 0.375 mmol), 3-(dimethylamino)propyl chloride hydrochloride (178 mg, 1.13 mmol) and potassium carbonate (311 mg, 2.25 mmol) in N,N-dimethylformamide (2 ml) was stirred at 100° C. for 6 h. After cooling to room temperature, water (50 ml) was added and extracted with ethyl acetate (50 ml×3). The combined organic layer was dried over magnesium sulfate and evaporated. To this residue (106 mg) was added methanolic hydrochloric acid and the mixture was concentrated in vacuo. The solid was recrystallized from ethanol/diisopropyl ether to give 99 mg (79%) of the title compound as a yellow solid.

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionextracted with ethyl acetate (50 ml×3)
  3. dry with materialThe combined organic layer was dried over magnesium sulfate
  4. customevaporated
  5. additionTo this residue (106 mg) was added methanolic hydrochloric acid
  6. concentrationthe mixture was concentrated in vacuo
  7. customThe solid was recrystallized from ethanol/diisopropyl ether

Sources & evidence

ORD record
ord-d585aa401ebd45c2b2e8221053880a56
Source dataset
uspto-grants-2004_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06686373B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes