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Potassium Carbonate → 6-(2,6-dichlorobenzoylamino)-2,3-dihydro-1-methyl-2-(pyridin-4-ylmethyl)-1H-pyrazolo[4,3-c]quinolin-3-one

HRID 613481
Notes
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Reaction equation

HRID 613481 reaction equation
Cl.[Cl:2][C:3]1[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[C:4]=1[C:5]([NH:7][C:8]1[C:17]2[N:16]=[CH:15][C:14]3[C:18](=[O:22])[NH:19][N:20]([CH3:21])[C:13]=3[C:12]=2[CH:11]=[CH:10][CH:9]=1)=[O:6].Cl.Cl[CH2:30][C:31]1[CH:36]=[CH:35][N:34]=[CH:33][CH:32]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:27][C:23]1[CH:24]=[CH:25][CH:26]=[C:3]([Cl:2])[C:4]=1[C:5]([NH:7][C:8]1[C:17]2[N:16]=[CH:15][C:14]3[C:18](=[O:22])[N:19]([CH2:30][C:31]4[CH:36]=[CH:35][N:34]=[CH:33][CH:32]=4)[N:20]([CH3:21])[C:13]=3[C:12]=2[CH:11]=[CH:10][CH:9]=1)=[O:6]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 745704-(Chloromethyl)pyridinium chlorideHCID 195929636-(2,6-dichlorobenzoylamino)-2,3-dihydro-1-methyl-1H-pyrazolo[4,3-c]quinolin-3-one hydrochloride

Product 1

HCID 195924656-(2,6-dichlorobenzoylamino)-2,3-dihydro-1-methyl-2-(pyridin-4-ylmethyl)-1H-pyrazolo[4,3-c]quinolin-3-one

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Procedure

A mixture of 6-(2,6-dichlorobenzoylamino)-2,3-dihydro-1-methyl-1H-pyrazolo[4,3-c]quinolin-3-one hydrochloride (85 mg), 4-chloromethylpyridine hydrochloride (40 mg) and potassium carbonate (111 mg) in dimethylformamide (1 ml) was stirred for 3 hours at ambient temperature. The mixture was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by column chromatography on silica gel to give 6-(2,6-dichlorobenzoylamino)-2,3-dihydro-1-methyl-2-(pyridin-4-ylmethyl)-1H-pyrazolo[4,3-c]quinolin-3-one.

Workup

  1. customThe mixture was partitioned between ethyl acetate and water
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-01452a8e5e7d4b87b305005f99133782
Source dataset
uspto-grants-1999_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06008230

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes