1-Ethyl-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid → Cis-7-[(2-Aminocyclopentyl)amino]-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

HRID 981507Notes

Reaction equation

HRID 981507 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].[C@@H:19]1([NH2:25])[CH2:23][CH2:22][CH2:21][C@@H:20]1[NH2:24]>N1C=CC=CC=1>[NH2:24][C@H:20]1[CH2:21][CH2:22][CH2:23][C@H:19]1[NH:25][C:10]1[CH:11]=[C:12]2[C:7]([C:6](=[O:15])[C:5]([C:16]([OH:18])=[O:17])=[CH:4][N:3]2[CH2:1][CH3:2])=[CH:8][C:9]=1[F:14]

Participants

4

Reactant 2

HCID 8005211-Ethyl-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 11412654cis-Cyclopentane-1,2-diamine

Product 1

HCID 54518842Cis-7-[(2-Aminocyclopentyl)amino]-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acidYield 63.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The procedure of Example 1 was followed using 0.6 g of 1-ethyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinoline-carboxylic acid and 1.0 g of cis-1,2-cyclopentanediamine in 4 ml of pyridine, giving 0.5 g of the desired product, m.p. 233°-235° C.

Sources & evidence

ORD record
ord-65bb6dc8a70a4652a49121afe397f6c4
Source dataset
uspto-grants-1991_02
Patent number
US04992449

Reaction notes

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