Diisopropylethylamine → 1-Cyclopropyl-7-[3,7-diazabicyclo[3.3.0]oct-1(5)-en-3-yl]-6,8-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

HRID 1534821Notes

Reaction equation

HRID 1534821 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.Br.Br.[C:23]12[CH2:30][NH:29][CH2:28][C:27]=1[CH2:26][NH:25][CH2:24]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:16])=[C:11]([N:25]4[CH2:26][C:27]5[CH2:28][NH:29][CH2:30][C:23]=5[CH2:24]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 81531DiisopropylethylamineHCID 5354141-Cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 232828491,2,3,4,5,6-Hexahydropyrrolo[3,4-c]pyrrole dihydrobromide

Product 1

HCID 98643051-Cyclopropyl-7-[3,7-diazabicyclo[3.3.0]oct-1(5)-en-3-yl]-6,8-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acidYield 85.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The suspension of 1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (14.7 g), 3,7-diazabicyclo[3.3.0] oct-1(5)-ene dihydrobromide (14.1 g) and diisopropyl-ethylamine (45 ml) in acetonitrile (1 l) was refluxed for 5 hours. The reaction mixture was cooled to room temperature and the produced precipitate was filtered and then washed with acetonitrile (200 ml) and water (200 ml) successively. Vacuum drying gave the title compound (16.6 g, yield 85%).

Workup

  1. temperaturewas refluxed for 5 hours
  2. filtrationthe produced precipitate was filtered
  3. washwashed with acetonitrile (200 ml) and water (200 ml) successively
  4. customVacuum drying

Sources & evidence

ORD record
ord-9649c3b11bc142849af6c545573dfaaa
Source dataset
uspto-grants-1992_02
Patent number
US05091384

Reaction notes

Loading…