Pyridine → HCID 13116432, compound

HRID 2295730Notes

Reaction equation

HRID 2295730 reaction equation
Cl[C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:18])[C:7]([C:15]([OH:17])=[O:16])=[C:8]3[S:14][CH2:13][CH2:12][N:9]32)=[CH:4][C:3]=1[F:19].[OH:20][CH2:21][CH2:22][N:23]1[CH2:28][CH2:27]C[CH2:25][CH2:24]1.[N:29]1C=CC=CC=1>>[F:19][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:2]=1[N:29]1[CH2:27][CH2:28][N:23]([CH2:22][CH2:21][OH:20])[CH2:24][CH2:25]1)[N:9]1[CH2:12][CH2:13][S:14][C:8]1=[C:7]([C:15]([OH:17])=[O:16])[C:6]2=[O:18]

Participants

4

Reactant 3

HCID 1049PyridineHCID 18232N-PiperidinoethanolHCID 104700458-chloro-7-fluoro-5-oxo-1,2-dihydro-5H-thiazolo(3,2-a)quinoline-4-carboxylic acid

Product 1

HCID 13116432HCID 13116432, compound

Procedure

A mixture of 500 mg (1.67 mmol) of 8-chloro-7-fluoro-5-oxo-1,2-dihydro-5H-thiazolo(3,2-a)-quinoline-4-carboxylic acid and 1.09 grams (8.34 mmol) of N-(beta-hydroxyethyl)-piperidine was suspended in 20 ml of pyridine and the mixture was heated to reflux for thirty two hours. When the reaction was completed, the mixture was cooled to a room temperature, crystals separated out therefrom were collected by filtration, successively washed with pyridine, ethanol and ether, and recrystallized from dimethyl formamide to give the title compound as pale yellow powders. Yield 426.6 mg (65 percent). Melting point 256° to 256.5° C. Elementary analysis calculated as C18H20FN3O4S: C 54.95, H 5.12, N 10.68; Found: C 54.52, H 5.14, N 10.73.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for thirty two hours
  3. customcrystals separated out
  4. filtrationtherefrom were collected by filtration
  5. washsuccessively washed with pyridine, ethanol and ether
  6. customrecrystallized from dimethyl formamide

Sources & evidence

ORD record
ord-c70ba637521f4d6894b515cfa00e7864
Source dataset
uspto-grants-1984_01
Patent number
US04426381

Reaction notes

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