1,8-Diazabicyclo(5.4.0)undec-7-ene → 7-(4-Methoxycarbonyl-2-isoindolinyl)-1-cyclopropyl-5-amino-6,8-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

HRID 1494805Notes

Reaction equation

HRID 1494805 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[C:9]([NH2:17])[C:10]([F:16])=[C:11](F)[C:12]=3[F:14])[C:7](=[O:18])[C:6]([C:19]([OH:21])=[O:20])=[CH:5]2)[CH2:3][CH2:2]1.Cl.[CH3:23][O:24][C:25]([C:27]1[CH:35]=[CH:34][CH:33]=[C:32]2[C:28]=1[CH2:29][NH:30][CH2:31]2)=[O:26].C1CCN2C(=NCCC2)CC1>CN(C=O)C>[CH3:23][O:24][C:25]([C:27]1[CH:35]=[CH:34][CH:33]=[C:32]2[C:28]=1[CH2:29][N:30]([C:11]1[C:12]([F:14])=[C:13]3[C:8]([C:7](=[O:18])[C:6]([C:19]([OH:21])=[O:20])=[CH:5][N:4]3[CH:1]3[CH2:3][CH2:2]3)=[C:9]([NH2:17])[C:10]=1[F:16])[CH2:31]2)=[O:26]

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 139109475-Amino-1-cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 19828511Methyl 2,3-dihydro-1H-isoindole-4-carboxylate--hydrogen chloride (1/1)

Product 1

HCID 151679127-(4-Methoxycarbonyl-2-isoindolinyl)-1-cyclopropyl-5-amino-6,8-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acidYield 39.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

298 mg of 1-cyclopropyl-5-amino-6,7,8-trifluoro-1,4- dihydro-4-oxoquinoline-3-carboxylic acid, 257 mg of 4-methoxycarbonylisoindoline hydrochloride, 532 mg of DBU, and 2ml of anhydrous DMF were processed in the same manner as in Example 20 to produce 181 mg of the target compound.

Sources & evidence

ORD record
ord-ee07d1acd1a6408ea6d98e574fc7e241
Source dataset
uspto-grants-1991_06
Patent number
US05026856

Reaction notes

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