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Dimethylformamide → HCID 53690243, compound

HRID 1415965
Notes
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Reaction equation

HRID 1415965 reaction equation
CN(C)C=O.[CH3:6][NH:7][C:8]1[CH:9]=[C:10]([N:16]2[C:25]3[C:20](=[CH:21][C:22]([F:28])=[C:23](F)[C:24]=3[Cl:26])[C:19](=[O:29])[C:18]([C:30]([OH:32])=[O:31])=[CH:17]2)[C:11]([F:15])=[CH:12][C:13]=1[F:14].Cl.Cl.[NH2:35][CH:36]1[CH2:39][NH:38][CH2:37]1.CN1CCCC1>C(O)C>[CH:36]([O:29][CH:19]([CH3:18])[CH3:20])([CH3:39])[CH3:37].[NH2:35][CH:36]1[CH2:39][N:38]([C:23]2[C:24]([Cl:26])=[C:25]3[C:20]([C:19](=[O:29])[C:18]([C:30]([OH:32])=[O:31])=[CH:17][N:16]3[C:10]3[C:11]([F:15])=[CH:12][C:13]([F:14])=[C:8]([NH:7][CH3:6])[CH:9]=3)=[CH:21][C:22]=2[F:28])[CH2:37]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 84541-MethylpyrrolidineHCID 13491919Azetidin-3-amine--hydrogen chloride (1/2)HCID 23284760HCID 23284760, compound

Product 2

HCID 7914Diisopropyl EtherHCID 53690243HCID 53690243, compoundYield 153.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

To 650 mg of N,N-dimethylformamide were added 150 mg of 1-(3-methylamino-4,6-difluorophenyl)-8-chloro-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid, 110 mg of 3-aminoazetidine dihydrochloride, and 250 mg of N-methylpyrrolidine. The solution was stirred at 90° C. for 1 hour. After 0.5 ml of ethanol was added, the reaction solution was allowed to cool down. The precipitate was collected by filtration and washed with ethanol and then diisopropyl ether to give 130 mg of the title compound.

Workup

  1. temperatureto cool down
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with ethanol

Sources & evidence

ORD record
ord-f5c1479931eb4329b4b6900ca0136665
Source dataset
uspto-grants-1999_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05910498

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes