3-Pyrrolidinemethanamine → 7-[3-(Aminomethyl)-1-pyrrolidinyl]-1-ethyl-5,6,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

HRID 542473Notes

Reaction equation

HRID 542473 reaction equation
[CH2:1]([N:3]1[C:12]2[C:7](=[C:8]([F:16])[C:9]([F:15])=[C:10](F)[C:11]=2[F:13])[C:6](=[O:17])[C:5]([C:18]([OH:20])=[O:19])=[CH:4]1)[CH3:2].[NH:21]1[CH2:25][CH2:24][CH:23]([CH2:26][NH2:27])[CH2:22]1>C(#N)C.C(OCC)C>[NH2:27][CH2:26][CH:23]1[CH2:24][CH2:25][N:21]([C:10]2[C:11]([F:13])=[C:12]3[C:7]([C:6](=[O:17])[C:5]([C:18]([OH:20])=[O:19])=[CH:4][N:3]3[CH2:1][CH3:2])=[C:8]([F:16])[C:9]=2[F:15])[CH2:22]1

Participants

5

Reactant 2

HCID 50687753-PyrrolidinemethanamineHCID 138510191-Ethyl-5,6,7,8-tetrafluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

Product 1

HCID 138510207-[3-(Aminomethyl)-1-pyrrolidinyl]-1-ethyl-5,6,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acidYield 82%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
45 °C

Procedure

To 1.0 g (3.5 mmol) of 1-ethyl-5,6,7,8-tetrafluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid in 20 ml of acetonitrile was added 1.05 g (6.9 mmol) of 1,8-diazobicyclo[5.4.0]undec-7-ene and 0.35 g (3.5 mmol) of 3-pyrrolidinemethanamine and the mixture was stirred at 45° C. for 18 hours, then refluxed one hour. The mixture was cooled, diluted with 50 ml of diethyl ether, and filtered. The solids were washed with ethanol and then diethyl ether to give 1.04 g (82%) of the title compound, mp>170° C. (decomposition).

Workup

  1. temperaturerefluxed one hour
  2. temperatureThe mixture was cooled
  3. filtrationfiltered
  4. washThe solids were washed with ethanol

Sources & evidence

ORD record
ord-161784c58b764fa5b8e92a568880dff1
Source dataset
uspto-grants-1987_04
Patent number
US04657913

Reaction notes

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