Diisopropylethylamine → 1-Cyclopropyl-7-[3,7-diazabicyclo[3.3.0] oct-1(5)-en-3-yl]-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

HRID 1534822Notes

Reaction equation

HRID 1534822 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:15])=[C:11](F)[CH:12]=3)[C:7](=[O:16])[C:6]([C:17]([OH:19])=[O:18])=[CH:5]2)[CH2:3][CH2:2]1.Br.Br.[C:22]12[CH2:29][NH:28][CH2:27][C:26]=1[CH2:25][NH:24][CH2:23]2.C(N(C(C)C)CC)(C)C>C(#N)C>[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:15])=[C:11]([N:24]4[CH2:25][C:26]5[CH2:27][NH:28][CH2:29][C:22]=5[CH2:23]4)[CH:12]=3)[C:7](=[O:16])[C:6]([C:17]([OH:19])=[O:18])=[CH:5]2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 52104221-Cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acidHCID 232828491,2,3,4,5,6-Hexahydropyrrolo[3,4-c]pyrrole dihydrobromide

Product 1

HCID 199082481-Cyclopropyl-7-[3,7-diazabicyclo[3.3.0] oct-1(5)-en-3-yl]-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acidYield 77%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-Cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (4.4 g) and 3,7-diazabicyclo[3.3.0] oct-1(5)-ene dihydrobromide (4.2 g) were added to diisopropyl ethylamine (11.6 ml) in acetonitrile (120 ml) and refluxed for 7 hours. The produced precipitate was filtered, washed with acetonitrile (100 ml), water (50 ml), ethanol (50 ml) and them ethyl ether (50 ml) to give the title compound (4.2 g, yield 77%).

Workup

  1. temperaturerefluxed for 7 hours
  2. filtrationThe produced precipitate was filtered
  3. washwashed with acetonitrile (100 ml), water (50 ml), ethanol (50 ml) and them ethyl ether (50 ml)

Sources & evidence

ORD record
ord-bf7be7dd5d854eccb4798dbbf45f1a84
Source dataset
uspto-grants-1992_02
Patent number
US05091384

Reaction notes

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