Potassium Bicarbonate → Ethyl 6-fluoro-1-methyl-7-[4-(5-methyl-2-oxo-1,3-dioxolen-4yl)methyl-1-piperazinyl]-4oxo-4H-[1,3-]thiazeto[3,2-a]quinoline-3-carboxylate

HRID 1533860Notes

Reaction equation

HRID 1533860 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[N:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1)[N:8]1[CH:18]([CH3:20])[S:19][C:7]1=[C:6]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:5]2=[O:26].C(=O)(O)[O-].[K+].Br[CH2:33][C:34]1[O:35][C:36](=[O:40])[O:37][C:38]=1[CH3:39]>CN(C)C=O>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[N:12]1[CH2:17][CH2:16][N:15]([CH2:33][C:34]3[O:35][C:36](=[O:40])[O:37][C:38]=3[CH3:39])[CH2:14][CH2:13]1)[N:8]1[CH:18]([CH3:20])[S:19][C:7]1=[C:6]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:5]2=[O:26]

Participants

5

Reactant 3

HCID 516893Potassium BicarbonateHCID 10249018Ethyl 6-fluoro-1-methyl-4-oxo-7-(piperazin-1-yl)-1,4-dihydro-[1,3]thiazeto[3,2-a]quinoline-3-carboxylateHCID 107741414-(Bromomethyl)-5-methyl-1,3-dioxol-2-one

Product 1

HCID 10413239Ethyl 6-fluoro-1-methyl-7-[4-(5-methyl-2-oxo-1,3-dioxolen-4yl)methyl-1-piperazinyl]-4oxo-4H-[1,3-]thiazeto[3,2-a]quinoline-3-carboxylateYield 66%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Ethyl 6-fluoro-1-methyl-4-oxo-7-(1-piperazinyl)-4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylate (3.88 g) and 1.23 g of potassium bicarbonate were suspended in 20 ml of N,N-dimethylformamide, 2.38 g of 4-bromomethyl-5-methyl-1,3-dioxolen-2-one was dropped thereinto with ice cooling, and the mixture was stirred for 3 hours. After the reaction, the solvent was evaporated in vacuo therefrom at 50° C. and the residue was extracted with chloroform containing a few amount of methanol. The extract was washed with water, dried, the solvent was evaporated therefrom and the residue was purified by a column chromatography (chloroform-methanol/silica gel) to give 3.32 g of desired product. M.p. 241°-243° C. (decompn.)

Workup

  1. customAfter the reaction
  2. customthe solvent was evaporated in vacuo
  3. extractionat 50° C. and the residue was extracted with chloroform containing a few amount of methanol
  4. washThe extract was washed with water
  5. customdried
  6. customthe solvent was evaporated
  7. customthe residue was purified by a column chromatography (chloroform-methanol/silica gel)

Sources & evidence

ORD record
ord-38399818fc4c4df2b2fb704634642e8c
Source dataset
uspto-grants-1992_02
Patent number
US05086049

Reaction notes

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