1,8-Diazabicyclo(5.4.0)undec-7-ene → 8-Chloro-1-cyclopropyl-7-(6,8-diazabicyclo[3.2.2]non-6-yl)-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

HRID 1073309Notes

Reaction equation

HRID 1073309 reaction equation
[Cl:1][C:2]1[C:3](F)=[C:4]([F:19])[CH:5]=[C:6]2[C:11]=1[N:10]([CH:12]1[CH2:14][CH2:13]1)[CH:9]=[C:8]([C:15]([OH:17])=[O:16])[C:7]2=[O:18].N12CCCN=C1CCCCC2.Cl.Cl.[CH:34]12[NH:42][CH2:41][CH:38]([NH:39][CH2:40]1)[CH2:37][CH2:36][CH2:35]2>C(#N)C>[Cl:1][C:2]1[C:3]([N:39]2[CH2:40][CH:34]3[NH:42][CH2:41][CH:38]2[CH2:37][CH2:36][CH2:35]3)=[C:4]([F:19])[CH:5]=[C:6]2[C:11]=1[N:10]([CH:12]1[CH2:14][CH2:13]1)[CH:9]=[C:8]([C:15]([OH:17])=[O:16])[C:7]2=[O:18]

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 98359418-Chloro-1-cyclopropyl-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 703770826,8-Diazabicyclo[3.2.2]nonane 2hcl

Product 1

HCID 150859408-Chloro-1-cyclopropyl-7-(6,8-diazabicyclo[3.2.2]non-6-yl)-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acidYield 60.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of 1.0 g (3.34 mmol) of 8-chloro-1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, 30 ml of acetonitrile, 1.52 g (10.0 mmol) of 1,8-diazabicyclo[5.4.0]undec7-ene, and 0.72 g (3.62 mmol) of 6,8-diazabicyclo [3.2.2]nonane, dihydrochloride was heated under reflux for 3 hr, then stirred at room temperature overnight. The precipitate was removed by filtration and washed with acetonitrile and ether to give 0.82 g of the title compound, mp 217°-220° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 3 hr
  3. customThe precipitate was removed by filtration
  4. washwashed with acetonitrile and ether

Sources & evidence

ORD record
ord-9205a1b4c28045359a5ef37aa765acd8
Source dataset
uspto-grants-1990_11
Patent number
US04968799

Reaction notes

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