1,8-Diazabicyclo(5.4.0)undec-7-ene → 7-(4-Nitro-2-isoindolinyl)-1-(4-fluorophenyl)-6,8-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

HRID 1494776Notes

Reaction equation

HRID 1494776 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:17]3[C:12](=[CH:13][C:14]([F:20])=[C:15](F)[C:16]=3[F:18])[C:11](=[O:21])[C:10]([C:22]([OH:24])=[O:23])=[CH:9]2)=[CH:4][CH:3]=1.[N+:25]([C:28]1[CH:36]=[CH:35][CH:34]=[C:33]2[C:29]=1[CH2:30][NH:31][CH2:32]2)([O-:27])=[O:26].C1CCN2C(=NCCC2)CC1>CN(C=O)C>[N+:25]([C:28]1[CH:36]=[CH:35][CH:34]=[C:33]2[C:29]=1[CH2:30][N:31]([C:15]1[C:16]([F:18])=[C:17]3[C:12]([C:11](=[O:21])[C:10]([C:22]([OH:24])=[O:23])=[CH:9][N:8]3[C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)=[CH:13][C:14]=1[F:20])[CH2:32]2)([O-:27])=[O:26]

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 137283301-(4-Fluorophenyl)-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acidHCID 197019494-Nitroisoindoline

Product 1

HCID 147958167-(4-Nitro-2-isoindolinyl)-1-(4-fluorophenyl)-6,8-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acidYield 35.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

200 mg of 1-(4-fluorophenyl)-6,7,8-trifluoro-1,4- dihydro-4-oxoquinoline-3-carboxylic acid, 176 mg of 4-nitroisoindoline, 164 mg of DBU, and 1.5 ml of anhydrous DMF were processed in the same manner as in Example 20 to produce 102 mg of the target compound.

Sources & evidence

ORD record
ord-cabdbae3949548de828fcc36ed8b8550
Source dataset
uspto-grants-1991_06
Patent number
US05026856

Reaction notes

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