Dabco → HCID 13565055, compound

HRID 745483Notes

Reaction equation

HRID 745483 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:16])=[C:11](F)[C:12]=3[F:14])[C:7](=[O:17])[C:6]([C:18]([OH:20])=[O:19])=[CH:5]2)[CH2:3][CH2:2]1.[S:21]1[CH:25]=[CH:24][CH:23]=[C:22]1[CH:26]1[CH2:31][NH:30][CH2:29][CH2:28][NH:27]1.C1N2CCN(CC2)C1>CS(C)=O>[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:16])=[C:11]([N:30]4[CH2:29][CH2:28][NH:27][CH:26]([C:22]5[S:21][CH:25]=[CH:24][CH:23]=5)[CH2:31]4)[C:12]=3[F:14])[C:7](=[O:17])[C:6]([C:18]([OH:20])=[O:19])=[CH:5]2)[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 9237DabcoHCID 5354141-Cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 27717262-Thiophen-2-yl-piperazine

Product 1

HCID 13565055HCID 13565055, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

2.8 g (0.01 mole) of 1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid (Example A) are heated to 140° C. together with 1.8 g (0.011 mole) of 2-(2-thienyl)piperazine and 2.2 g (0.02 mole) of 1,4-diazobicyclo[2.2.2]octane in 6 ml of DMSO for 2 hours. The mixture is concentrated under high vacuum, the residue is stirred with 20 ml of water, and the precipitate is filtered off with suction and boiled in 20 ml of methanol. 2.4 g (56% of theory) of 1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxo-7-[3-(2-thienyl)-1-piperazinyl]-3-quinolinecarboxylic acid of melting point 252°-254° C. (with decomposition) are obtained. The melting point remains unchanged after recrystallization from glycol monomethyl ether.

Workup

  1. concentrationThe mixture is concentrated under high vacuum
  2. filtrationthe precipitate is filtered off with suction

Sources & evidence

ORD record
ord-50184328c14e40ba93c5e921db29294a
Source dataset
uspto-grants-1986_07
Patent number
US04599334

Reaction notes

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