Piperazine → Ethyl 6-fluoro-1-methyl-4-oxo-7-(piperazin-1-yl)-1,4-dihydro-[1,3]thiazeto[3,2-a]quinoline-3-carboxylate

HRID 1905429Notes

Reaction equation

HRID 1905429 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1F)[N:8]1[CH:13]([CH3:15])[S:14][C:7]1=[C:6]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:5]2=[O:21].[NH:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1>CN(C)C=O>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[N:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1)[N:8]1[CH:13]([CH3:15])[S:14][C:7]1=[C:6]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:5]2=[O:21]

Participants

4

Reactant 2

HCID 4837PiperazineHCID 10380740Ethyl 6,7-difluoro-1-methyl-4-oxo-1,4-dihydro-[1,3]thiazeto[3,2-a]quinoline-3-carboxylate

Product 1

HCID 10249018Ethyl 6-fluoro-1-methyl-4-oxo-7-(piperazin-1-yl)-1,4-dihydro-[1,3]thiazeto[3,2-a]quinoline-3-carboxylateYield 49.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Ethyl 6,7-difluoro-1-methyl-4-oxo-4H-(1,3)thiazeto(3,2-a)quinoline-3-carboxylate (5.0 g) was suspended in 150 ml of N,N-dimethylformamide and the suspension was stirred with 4.6 g of piperazine at room temperature for 48 hours. N,N-Dimethylformamide was evaporated in vacuo and to the residue was added ice water to collect the crystals by filtration. Purification by a column chromatography (silica gel/chloroform-methanol (1:1)) gave 3.0 g of desired compound, m.p. 224° C. (decompn.).

Workup

  1. customN,N-Dimethylformamide was evaporated in vacuo and to the residue
  2. additionwas added ice water
  3. customto collect the crystals
  4. filtrationby filtration
  5. customPurification by a column chromatography (silica gel/chloroform-methanol (1:1))

Sources & evidence

ORD record
ord-212ce1c2cc9e4a86a47950be09e11fb3
Source dataset
uspto-grants-1989_06
Patent number
US04843070

Reaction notes

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