7-Chloro-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid → HCID 14839363, compound

HRID 248474Notes

Reaction equation

HRID 248474 reaction equation
[CH3:1][C:2]1[C:3]2[CH:16]=[CH:15][CH:14]=[CH:13][C:4]=2[S:5][C:6]=1[CH:7]1[CH2:12][NH:11][CH2:10][CH2:9][NH:8]1.Cl[C:18]1[CH:27]=[C:26]2[C:21]([C:22](=[O:33])[C:23]([C:30]([OH:32])=[O:31])=[CH:24][N:25]2[CH2:28][CH3:29])=[CH:20][C:19]=1[F:34]>N1C=CC=CC=1>[CH2:28]([N:25]1[C:26]2[C:21](=[CH:20][C:19]([F:34])=[C:18]([N:11]3[CH2:10][CH2:9][NH:8][CH:7]([C:6]4[S:5][C:4]5[CH:13]=[CH:14][CH:15]=[CH:16][C:3]=5[C:2]=4[CH3:1])[CH2:12]3)[CH:27]=2)[C:22](=[O:33])[C:23]([C:30]([OH:32])=[O:31])=[CH:24]1)[CH3:29]

Participants

4

Reactant 2

HCID 4831697-Chloro-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 19763583HCID 19763583, compound

Product 1

HCID 14839363HCID 14839363, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A 2 g portion of 2-(3-methylbenzo[b]thien-2-yl)piperazine was added to 7 ml of pyridine. A 780 mg portion of 7-chloro-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid was added and the mixture was heated in a pressure bottle, under argon at 120°-130° C. for 18 hours. The solid was collected, washed with pyridine, then ether and recrystallized from dimethylformamide, giving 540 mg of the desired product, mp 302°-304° C. (dec.).

Workup

  1. temperaturethe mixture was heated in a pressure bottle, under argon at 120°-130° C. for 18 hours
  2. customThe solid was collected
  3. washwashed with pyridine
  4. customether and recrystallized from dimethylformamide

Sources & evidence

ORD record
ord-cc29be54ac08460ba8c24a02ea4917cb
Source dataset
uspto-grants-1993_05
Patent number
US05210193

Reaction notes

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