6,7,8-Trifluoro-1,4-dihydro-4-oxo-1-(2-thiazolyl)-3-quinolinecarboxylic acid → 7-[3[(Ethylamino)methyl]-1-pyrrolidinyl]-6,8-difluoro-1,4-dihydro-4-oxo-1-(2-thiazolyl)-3-quinolinecarboxylic acid

HRID 2290522Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([F:13])[C:11]=1F)[N:8]([C:14]1[S:15][CH:16]=[CH:17][N:18]=1)[CH:7]=[C:6]([C:19]([OH:21])=[O:20])[C:5]2=[O:22].[CH2:23]([NH:25][CH2:26][CH:27]1[CH2:31][CH2:30][NH:29][CH2:28]1)[CH3:24]>C(#N)C>[CH2:23]([NH:25][CH2:26][CH:27]1[CH2:31][CH2:30][N:29]([C:11]2[C:10]([F:13])=[C:9]3[C:4]([C:5](=[O:22])[C:6]([C:19]([OH:21])=[O:20])=[CH:7][N:8]3[C:14]3[S:15][CH:16]=[CH:17][N:18]=3)=[CH:3][C:2]=2[F:1])[CH2:28]1)[CH3:24]

Participants

Conditions

Temperature: 60 °C

Procedure

To 1.0 g (3.06 mmol) of the 6,7,8-trifluoro-1,4-dihydro-4-oxo-1-(2-thiazolyl)-3-quinolinecarboxylic acid in 10 ml of acetonitrile was added 0.46 g of 1,8-diazobicyclo[5.4.0]undec-7-ene and 0.39 g of 3-[(ethylamino)methyl]pyrrolidine. The reaction was warmed to 60° C. for one hour and was then taken to room temperature and stirred overnight. The solids were filtered and washed with ether to give 0.32 g of 7-[3[(ethylamino)methyl]-1-pyrrolidinyl]-6,8-difluoro-1,4-dihydro-4-oxo-1-(2-thiazolyl)-3-quinolinecarboxylic acid, mp 200°-207° (dec).

Workup

customwas then taken to room temperature
filtrationThe solids were filtered
washwashed with ether

Sources & evidence

ORD record: ord-0497da5386684e708b28b149aca592c9
Source dataset: uspto-grants-1986_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04617308

Reaction notes

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