Water → HCID 23442443, compound

HRID 2119659Notes

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

Participants

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

temperatureAfter cooling to room temperature
extractionextracted with ethyl acetate (50 ml×3)
dry with materialThe combined organic layer was dried over magnesium sulfate
customevaporated
additionTo this residue (106 mg) was added methanolic hydrochloric acid
concentrationthe mixture was concentrated in vacuo
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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