Ethyl-pyrrolidin-3-ylmethyl-amine → 1-Cyclohexyl-7-[3-[(ethylamino)methyl]-1-pyrrolidinyl]-6,8-difluoro1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

HRID 980692Notes

Reaction equation

HRID 980692 reaction equation
[CH:1]1([N:7]2[C:16]3[C:11](=[CH:12][C:13]([F:19])=[C:14](F)[C:15]=3[F:17])[C:10](=[O:20])[C:9]([C:21]([OH:23])=[O:22])=[CH:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:24]([NH:26][CH2:27][CH:28]1[CH2:32][CH2:31][NH:30][CH2:29]1)[CH3:25]>C(#N)C>[CH:1]1([N:7]2[C:16]3[C:11](=[CH:12][C:13]([F:19])=[C:14]([N:30]4[CH2:31][CH2:32][CH:28]([CH2:27][NH:26][CH2:24][CH3:25])[CH2:29]4)[C:15]=3[F:17])[C:10](=[O:20])[C:9]([C:21]([OH:23])=[O:22])=[CH:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 13491786Ethyl-pyrrolidin-3-ylmethyl-amineHCID 137728341-Cyclohexyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

Product 1

HCID 137728131-Cyclohexyl-7-[3-[(ethylamino)methyl]-1-pyrrolidinyl]-6,8-difluoro1,4-dihydro-4-oxo-3-quinolinecarboxylic acidYield 80.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To 0.80 g (2.46 mmol) of 1-cyclohexyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid in 15 ml of acetonitrile was added 0.37 g (2.46 mmol) of 1,8-diazobicyclo[5.4.0]undec7-ene and 0.33 g (2.58 mmol) of 3-[(ethylamino)methyl]pyrrolidine. The mixture was refluxed for one hour, cooled, filtered, and the solids washed with ether to give 0.86 g of 1-cyclohexyl-7-[3-[(ethylamino)methyl]-1-pyrrolidinyl]-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, mp 194°-196° C.

Workup

  1. temperatureThe mixture was refluxed for one hour
  2. temperaturecooled
  3. filtrationfiltered
  4. washthe solids washed with ether

Sources & evidence

ORD record
ord-ad359e4ed266475cb60042718ad0e17c
Source dataset
uspto-grants-1987_01
Patent number
US04638067

Reaction notes

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