Triethylamine → 7-[3-(Aminomethyl)-3-methyl-1-pyrrolidinyl]-8-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

HRID 622378Notes

Reaction equation

HRID 622378 reaction equation
[Cl:1][C:2]1[C:3](F)=[C:4]([F:19])[CH:5]=[C:6]2[C:11]=1[N:10]([CH:12]1[CH2:14][CH2:13]1)[CH:9]=[C:8]([C:15]([OH:17])=[O:16])[C:7]2=[O:18].C(N(CC)CC)C.[CH3:28][C:29]1([CH2:34][NH2:35])[CH2:33][CH2:32][NH:31][CH2:30]1>C(#N)C>[NH2:35][CH2:34][C:29]1([CH3:28])[CH2:33][CH2:32][N:31]([C:3]2[C:2]([Cl:1])=[C:11]3[C:6]([C:7](=[O:18])[C:8]([C:15]([OH:17])=[O:16])=[CH:9][N:10]3[CH:12]3[CH2:14][CH2:13]3)=[CH:5][C:4]=2[F:19])[CH2:30]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 98359418-Chloro-1-cyclopropyl-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 14235023(3-Methylpyrrolidin-3-YL)methanamine

Product 1

HCID 142350247-[3-(Aminomethyl)-3-methyl-1-pyrrolidinyl]-8-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acidYield 95%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To 1.05 g (3.50 mmol) of 8-chloro-1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid was added 15 ml of acetonitrile, 1.0 g (9.9 mmol) of triethylamine and 0.7 g (6 mmol) of the 3-methyl-3-pyrrolidinemethanamine. The mixture was refluxed 18 hours and cooled. Filtration gave 1.31 g of the title compound, mp 189°-191° C.

Workup

  1. temperatureThe mixture was refluxed 18 hours
  2. temperaturecooled
  3. filtrationFiltration

Sources & evidence

ORD record
ord-45aacf0606b0430f97d7387f01cd27c1
Source dataset
uspto-grants-1988_09
Patent number
US04771055

Reaction notes

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