1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 13565826, compound

HRID 1589574Notes

Reaction equation

HRID 1589574 reaction equation
[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:15])=[C:10](F)[C:11]=2[F:13])[C:6](=[O:16])[C:5]([C:17]([OH:19])=[O:18])=[CH:4]1)[CH3:2].[N:20]12[CH2:30][CH2:29][CH2:28][N:27]=[C:26]1[CH2:25]CCC[CH2:21]2.N12CC(CC1)NCC2>C(#N)C>[N:20]12[CH2:21][CH:28]([CH2:29][CH2:30]1)[N:27]([C:10]1[C:11]([F:13])=[C:12]3[C:7]([C:6](=[O:16])[C:5]([C:17]([OH:19])=[O:18])=[CH:4][N:3]3[CH2:1][CH3:2])=[CH:8][C:9]=1[F:15])[CH2:26][CH2:25]2

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 98351791-Ethyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 123740771,4-Diazabicyclo[3.2.1]octane

Product 1

HCID 13565826HCID 13565826, compoundYield 20.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 0.81 g (3 mmole) 1-ethyl-6,7,8-trifluoro-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid and 0.46 g (3 mmole) 1,8-diazabicyclo[5.4.0]undec-7-ene in 10 ml acetonitrile was added 0.37 g (3.3 mmole) 1,4-diazabicyclo[3.2.1]octane and the mixture stirred at reflux 51/2 hours. After standing overnight at room temperature a yellowish solid was filtered, washed with acetonitrile and ether and dried in vacuo to afford 0.22 g product, mp decomposed above 233° C.

Workup

  1. temperatureat reflux 51/2 hours
  2. filtrationa yellowish solid was filtered
  3. washwashed with acetonitrile and ether
  4. customdried in vacuo

Sources & evidence

ORD record
ord-9892928dba7a4336a9fd87e9f5ea15bf
Source dataset
uspto-grants-1986_02
Patent number
US04571396

Reaction notes

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