8-Chloro-1-cyclopropyl-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid → 8-Chloro-1-cyclopropyl-7-(trans-3-ethylamino-4-methylthio-1-pyrrolidinyl)-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

HRID 36717

Reaction equation

HRID 36717 reaction equation
[CH2:1]([NH:3][C@H:4]1[C@H:8]([S:9][CH3:10])[CH2:7][NH:6][CH2:5]1)[CH3:2].[Cl:11][C:12]1[C:13](F)=[C:14]([F:29])[CH:15]=[C:16]2[C:21]=1[N:20]([CH:22]1[CH2:24][CH2:23]1)[CH:19]=[C:18]([C:25]([OH:27])=[O:26])[C:17]2=[O:28]>>[Cl:11][C:12]1[C:13]([N:6]2[CH2:7][C@@H:8]([S:9][CH3:10])[C@H:4]([NH:3][CH2:1][CH3:2])[CH2:5]2)=[C:14]([F:29])[CH:15]=[C:16]2[C:21]=1[N:20]([CH:22]1[CH2:24][CH2:23]1)[CH:19]=[C:18]([C:25]([OH:27])=[O:26])[C:17]2=[O:28]

Participants

3

Reactant 2

HCID 98359418-Chloro-1-cyclopropyl-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 15069979trans-3-Ethylamino-4-methylthio-pyrrolidine

Product 1

HCID 150700828-Chloro-1-cyclopropyl-7-(trans-3-ethylamino-4-methylthio-1-pyrrolidinyl)-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

Procedure

The reaction is carried out analogously to Example 13 with trans-3-ethylamino-4-methylthio-pyrrolidine and 8-chloro-1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid to give 8-chloro-1-cyclopropyl-7-(trans-3-ethylamino-4-methylthio-1-pyrrolidinyl)-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, melting point: 217°-218° C. (with decomposition).

Sources & evidence

ORD record
ord-0846063899fa4b59a49b5136ec458cef
Source dataset
uspto-grants-1995_05
Patent number
US05416096

Linked notes

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