Triethylamine → 1-(4-Fluorophenyl)-6,8-difluoro-7-(3-methyl-3-trifluoroacetamido-1-azetidinyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

HRID 1651397Notes

Reaction equation

HRID 1651397 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:17]3[C:12](=[CH:13][C:14]([F:20])=[C:15](F)[C:16]=3[F:18])[C:11](=[O:21])[C:10]([C:22]([OH:24])=[O:23])=[CH:9]2)=[CH:4][CH:3]=1.Cl.[CH3:26][C:27]1([NH:31][C:32](=[O:37])[C:33]([F:36])([F:35])[F:34])[CH2:30][NH:29][CH2:28]1.C(N(CC)CC)C>N1C=CC=CC=1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:17]3[C:12](=[CH:13][C:14]([F:20])=[C:15]([N:29]4[CH2:30][C:27]([CH3:26])([NH:31][C:32](=[O:37])[C:33]([F:36])([F:35])[F:34])[CH2:28]4)[C:16]=3[F:18])[C:11](=[O:21])[C:10]([C:22]([OH:24])=[O:23])=[CH:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 137283301-(4-Fluorophenyl)-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acidHCID 200879193-Methyl-3-trifluoroacetamidoazetidine hydrochloride

Product 1

HCID 100746561-(4-Fluorophenyl)-6,8-difluoro-7-(3-methyl-3-trifluoroacetamido-1-azetidinyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 1 g (3 mmoles) of 1-(4-fluorophenyl)-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, 0.98 g (4.5 mmoles) of 3-methyl-3-trifluoroacetamidoazetidine hydrochloride and 0.6 g (6 mmoles) of triethylamine is heated under reflux for 3 hours in 10 ml of pyridine.

Workup

  1. temperatureis heated

Sources & evidence

ORD record
ord-b659e44f6d9d4199b79a29fefd38d6f8
Source dataset
uspto-grants-1990_05
Patent number
US04927926

Reaction notes

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