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

HRID 1494770Notes

Reaction equation

HRID 1494770 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[C:9]([NH:17][CH2:18][CH2:19][OH:20])[C:10]([F:16])=[C:11](F)[C:12]=3[F:14])[C:7](=[O:21])[C:6]([C:22]([OH:24])=[O:23])=[CH:5]2)[CH2:3][CH2:2]1.[CH2:25]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH2:27][NH:26]1.C1CCN2C(=NCCC2)CC1>CN(C=O)C>[CH2:25]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH2:27][N:26]1[C:11]1[C:12]([F:14])=[C:13]2[C:8]([C:7](=[O:21])[C:6]([C:22]([OH:24])=[O:23])=[CH:5][N:4]2[CH:1]2[CH2:3][CH2:2]2)=[C:9]([NH:17][CH2:18][CH2:19][OH:20])[C:10]=1[F:16]

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 422478IsoindolineHCID 198284861-Cyclopropyl-5(2-hydroxyethylamino)-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

Product 1

HCID 147957877-(2-Isoindolinyl)-1-cyclopropyl-5(2-hydroxyethylamino)-6,8-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acidYield 42.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

205 mg of 1-cyclopropyl-5(2-hydroxyethylamino)-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid, 119 mg of isoindoline, 182 mg of DBU, and 1.5 ml of anhydrous DMF were processed in the same manner as in Example 20 to produce 113 mg of the target compound.

Sources & evidence

ORD record
ord-f5995ad2d4e247edbb8bc4ba1fc53a45
Source dataset
uspto-grants-1991_06
Patent number
US05026856

Reaction notes

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