HCID 417149, compound → HCID 13116431, compound

HRID 2295729Notes

Reaction equation

HRID 2295729 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][CH:21]([CH2:29][O:30][CH3:31])[CH2:22][N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1>N1C=CC=CC=1>[F:19][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:2]=1[N:26]1[CH2:25][CH2:24][N:23]([CH2:22][CH:21]([OH:20])[CH2:29][O:30][CH3:31])[CH2:28][CH2:27]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 2

HCID 417149HCID 417149, compoundHCID 104700458-chloro-7-fluoro-5-oxo-1,2-dihydro-5H-thiazolo(3,2-a)quinoline-4-carboxylic acid

Product 1

HCID 13116431HCID 13116431, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

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 1.45 grams (8.3 mmol) of N-(2-hydroxy-3-methoxy-1-propyl)-piperazine was suspended in 20 ml of pyridine and the mixture was heated to reflux for thirty six hours. When the reaction was completed, pyridine was evaporated therefrom under reduced pressure and ethanol was added to the residue. Insoluble matters were filtered, washed with ether, and recrystallized from acetonitrile to give the title compound as flaky crystals. Yield 397.8 mg (54.5 percent). Melting point 224° C. Elementary analysis calculated as C20H24FN3O5S: C 54.91, H 5.53, N 9.60; Found: C 54.94, H 5.55, N 9.60.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for thirty six hours
  3. custompyridine was evaporated
  4. additionunder reduced pressure and ethanol was added to the residue
  5. filtrationInsoluble matters were filtered
  6. washwashed with ether
  7. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-92cd82acd1144d3285bd69835e0b6b9d
Source dataset
uspto-grants-1984_01
Patent number
US04426381

Reaction notes

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