Dabco → 1-(1-Fluoromethyl-1-methyl-2-fluoroethyl)-6-fluoro-7-[(1S,6R)-2-oxa-5,8-diazabicyclo[4.3.0]non-8-yl]-1,4-dihydro-4-oxo-3-quinolinecarboxylic Acid

HRID 2302232Notes

Reaction equation

HRID 2302232 reaction equation
[F:1][CH2:2][C:3]([N:7]1[C:16]2[C:11](=[CH:12][C:13]([F:18])=[C:14](F)[CH:15]=2)[C:10](=[O:19])[C:9]([C:20]([OH:22])=[O:21])=[CH:8]1)([CH3:6])[CH2:4][F:5].[C@H:23]12[CH2:31][NH:30][CH2:29][C@H:28]1[NH:27][CH2:26][CH2:25][O:24]2.N12CCN(CC1)CC2>C(#N)C>[F:1][CH2:2][C:3]([N:7]1[C:16]2[C:11](=[CH:12][C:13]([F:18])=[C:14]([N:30]3[CH2:31][C@H:23]4[C@H:28]([NH:27][CH2:26][CH2:25][O:24]4)[CH2:29]3)[CH:15]=2)[C:10](=[O:19])[C:9]([C:20]([OH:22])=[O:21])=[CH:8]1)([CH3:6])[CH2:4][F:5]

Participants

5

Reactant 3

HCID 9237DabcoHCID 18459849HCID 18459849, compoundHCID 55287490Rac-(4ar,7as)-octahydropyrrolo[3,4-b]morpholine

Product 1

HCID 540502771-(1-Fluoromethyl-1-methyl-2-fluoroethyl)-6-fluoro-7-[(1S,6R)-2-oxa-5,8-diazabicyclo[4.3.0]non-8-yl]-1,4-dihydro-4-oxo-3-quinolinecarboxylic Acid

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 1-(1-fluoromethyl-1-methyl-2-fluoroethyl)-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid (400 mg, 1.26 mmol), (1S,6R)-2-oxa-5,8-diazabicyclo[4.3.0]nonane (176 mg, 1.39 mmol) and 1,4-diazabicyclo[2.2.2]octane (141 mg, 1.26 mmol) in absol. acetonitrile (20 ml) is heated under reflux overnight. After cooling the reaction mixture to room temperature, the precipitated crystals are filtered off and washed with acetonitrile.

Workup

  1. temperatureunder reflux overnight
  2. filtrationthe precipitated crystals are filtered off
  3. washwashed with acetonitrile

Sources & evidence

ORD record
ord-4ffc6aeec65648a59e63338a164e6077
Source dataset
uspto-grants-2002_08
Patent number
US06432948B1

Reaction notes

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