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1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 13933098, compound

HRID 580574
Notes
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Reaction equation

HRID 580574 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:16])=[C:11](F)[C:12]=3[F:14])[C:7](=[O:17])[C:6]([C:18]([OH:20])=[O:19])=[CH:5]2)[CH2:3][CH2:2]1.[C:21]([N:24]([CH:26]1[CH:30]([CH3:31])[CH2:29][NH:28][CH2:27]1)[CH3:25])(=[O:23])[CH3:22].C1CCN2C(=NCCC2)CC1>C(#N)C>[C:21]([N:24]([CH:26]1[CH:30]([CH3:31])[CH2:29][N:28]([C:11]2[C:12]([F:14])=[C:13]3[C:8]([C:7](=[O:17])[C:6]([C:18]([OH:20])=[O:19])=[CH:5][N:4]3[CH:1]3[CH2:3][CH2:2]3)=[CH:9][C:10]=2[F:16])[CH2:27]1)[CH3:25])(=[O:23])[CH3:22]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 5354141-Cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 201341253-(N-acetyl-N-methylamino)-4-methylpyrrolidine

Product 1

HCID 13933098HCID 13933098, compoundYield 75.6%

Reagents, catalysts & solvents 1

HCID 6342Acetonitrile
Solvent

Procedure

A mixture of 1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid (0.5 g), anhydrous acetonitrile (5 ml), 3-(N-acetyl-N-methylamino)-4-methylpyrrolidine (0.42 g) and DBU (0.27 g) was refluxed for an hour and allowed to stand overnight. The resulting precipitate was collected by filtration and washed with acetonitrile-ether to give the title compound (0.56 g) as pale yellow powder.

Workup

  1. temperaturewas refluxed for an hour
  2. filtrationThe resulting precipitate was collected by filtration
  3. washwashed with acetonitrile-ether

Sources & evidence

ORD record
ord-b81aa4127a144cfaaf5e2fcec1faa46a
Source dataset
uspto-grants-1988_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04753953

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes