1,8-Diazabicyclo(5.4.0)undec-7-ene → 7-(5-Ethylamino-2-isoindolinyl)-1-ethyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

HRID 1494737Notes

Reaction equation

HRID 1494737 reaction equation
[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:14])=[C:10](F)[CH:11]=2)[C:6](=[O:15])[C:5]([C:16]([OH:18])=[O:17])=[CH:4]1)[CH3:2].[CH2:19]([NH:21][C:22]1[CH:23]=[C:24]2[C:28](=[CH:29][CH:30]=1)[CH2:27][NH:26][CH2:25]2)[CH3:20].C1CCN2C(=NCCC2)CC1>CN(C=O)C>[CH2:19]([NH:21][C:22]1[CH:23]=[C:24]2[C:28](=[CH:29][CH:30]=1)[CH2:27][N:26]([C:10]1[CH:11]=[C:12]3[C:7]([C:6](=[O:15])[C:5]([C:16]([OH:18])=[O:17])=[CH:4][N:3]3[CH2:1][CH3:2])=[CH:8][C:9]=1[F:14])[CH2:25]2)[CH3:20]

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 8005211-Ethyl-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 147958635-Ethylaminoisoindoline

Product 1

HCID 147958137-(5-Ethylamino-2-isoindolinyl)-1-ethyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acidYield 49.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

177 mg of 1-ethyl-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid, 136 mg of 5-ethylaminoisoindoline, 213 mg of DBU, and 1.5 ml of anhydrous DMF were processed in the same manner as in Example 1 to produce 138 mg of the target compound.

Sources & evidence

ORD record
ord-4d626023e24744d4a60097a10e608a6b
Source dataset
uspto-grants-1991_06
Patent number
US05026856

Reaction notes

Loading…