Dimethylformamide → ethyl 6-fluoro-1-methyl-4-oxo-7-[4-(2-pyrimidinyl)piperazin-1-yl]-1H,4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylate

HRID 2293975Notes

Reaction equation

HRID 2293975 reaction equation
CN(C)C=O.[F:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][C:16]=1F)[N:13]1[CH:18]([CH3:20])[S:19][C:12]1=[C:11]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:10]2=[O:26].Cl.Cl.[N:29]1[CH:34]=[CH:33][CH:32]=[N:31][C:30]=1[N:35]1[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]1.C1CCN2C(=NCCC2)CC1>O>[F:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][C:16]=1[N:38]1[CH2:39][CH2:40][N:35]([C:30]3[N:29]=[CH:34][CH:33]=[CH:32][N:31]=3)[CH2:36][CH2:37]1)[N:13]1[CH:18]([CH3:20])[S:19][C:12]1=[C:11]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:10]2=[O:26]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 10380740Ethyl 6,7-difluoro-1-methyl-4-oxo-1,4-dihydro-[1,3]thiazeto[3,2-a]quinoline-3-carboxylateHCID 116802722-Piperazinylpyrimidine dihydrochloride

Product 1

HCID 21473341ethyl 6-fluoro-1-methyl-4-oxo-7-[4-(2-pyrimidinyl)piperazin-1-yl]-1H,4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylateYield 96%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 16 ml of N,N-dimethylformamide were added 2.0 g (0.0064 mole) of ethyl 6,7-difluoro-1-methyl-4-oxo-1H,4H-[1,3]-thiazeto[3,2-a]quinoline-3-carboxylate, 3.0 g (0.0129 mole) of 1-(2-pyrimidinyl)piperazine dihydrochloride and 3.9 g (0.0256 mole) of 1,8-diazabicyclo[5.4.0]-7-undecene, and the mixture was stirred at room temperature for 5 days. The reaction mixture was added to water, and crystals precipitated were collected by filtration, washed with water and dried to obtain 2.8 g of ethyl 6-fluoro-1-methyl-4-oxo-7-[4-(2-pyrimidinyl)piperazin-1-yl]-1H,4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylate as pale yellow powder.

Workup

  1. customprecipitated
  2. filtrationwere collected by filtration
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-8f3979324d8346fa944fc65935bc6241
Source dataset
uspto-grants-1997_11
Patent number
US05688791

Reaction notes

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