7-Chloro-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid → HCID 14839362, compound

HRID 2165618Notes

Reaction equation

HRID 2165618 reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][C:5]2[S:6][C:7]([CH:10]3[CH2:15][NH:14][CH2:13][CH2:12][NH:11]3)=[C:8]([CH3:9])[C:4]=2[CH:3]=1.Cl[C:19]1[CH:28]=[C:27]2[C:22]([C:23](=[O:34])[C:24]([C:31]([OH:33])=[O:32])=[CH:25][N:26]2[CH2:29][CH3:30])=[CH:21][C:20]=1[F:35]>N1C=CC=CC=1>[Cl:1][C:2]1[CH:17]=[CH:16][C:5]2[S:6][C:7]([CH:10]3[NH:11][CH2:12][CH2:13][N:14]([C:19]4[CH:28]=[C:27]5[C:22]([C:23](=[O:34])[C:24]([C:31]([OH:33])=[O:32])=[CH:25][N:26]5[CH2:29][CH3:30])=[CH:21][C:20]=4[F:35])[CH2:15]3)=[C:8]([CH3:9])[C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 4831697-Chloro-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 19763545HCID 19763545, compound

Product 1

HCID 14839362HCID 14839362, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A 3.0 g portion of 2-(5-chloro-3-methylbenzo[b]thien-2-yl)piperazine was added to 5 ml of pyridine. A 1.01 g 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 130°-135° C. for 18 hours, then cooled and placed in an ice bath. The resulting crystals were collected, washed with cold pyridine, dichloromethane and ether and recrystallized from dimethylformamide, giving 401 mg of the desired product, mp 300°-305° C.

Workup

  1. temperaturethe mixture was heated in a pressure bottle, under argon at 130°-135° C. for 18 hours
  2. temperaturecooled
  3. customplaced in an ice bath
  4. customThe resulting crystals were collected
  5. washwashed with cold pyridine, dichloromethane and ether
  6. customrecrystallized from dimethylformamide

Sources & evidence

ORD record
ord-df9a72f34d074e08b98b7f9aeb025d17
Source dataset
uspto-grants-1990_07
Patent number
US04940710

Reaction notes

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