Ethyl-pyrrolidin-3-ylmethyl-amine → 7-[3-[(Ethylamino)methyl]-1-pyrrolidinyl]-6,8-difluoro-1,4-dihydro-1-methylamino-4-oxo-3-quinolinecarboxylic acid

HRID 364055Notes

Reaction equation

HRID 364055 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([F:13])[C:11]=1F)[N:8]([NH:14][CH3:15])[CH:7]=[C:6]([C:16]([OH:18])=[O:17])[C:5]2=[O:19].[CH2:20]([NH:22][CH2:23][CH:24]1[CH2:28][CH2:27][NH:26][CH2:25]1)[CH3:21]>C(#N)C>[CH2:20]([NH:22][CH2:23][CH:24]1[CH2:28][CH2:27][N:26]([C:11]2[C:10]([F:13])=[C:9]3[C:4]([C:5](=[O:19])[C:6]([C:16]([OH:18])=[O:17])=[CH:7][N:8]3[NH:14][CH3:15])=[CH:3][C:2]=2[F:1])[CH2:25]1)[CH3:21]

Participants

4

Reactant 2

HCID 13491786Ethyl-pyrrolidin-3-ylmethyl-amineHCID 135580371-Methylamino-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

Product 1

HCID 137119917-[3-[(Ethylamino)methyl]-1-pyrrolidinyl]-6,8-difluoro-1,4-dihydro-1-methylamino-4-oxo-3-quinolinecarboxylic acidYield 65.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To 0.75 g (2.75 mmol) of the 6,7,8-trifluoro-1,4-dihydro-1-methylamino-4-oxo-3-quinolinecarboxylic acid in 15 ml of acetonitrile was added 0.44 g (1.05 equivalent) of 1,8-diazobicyclo[5.4.0]undec-7-ene, and 0.352 g (1.0 equivalent) of N-ethyl-3-pyrrolidinemethanamine. The mixture was refluxed for one hour and then stirred at room temperature overnight. The solids were filtered to give 0.68 g of 7-[3-[(ethylamino)methyl]-1-pyrrolidinyl]-6,8-difluoro-1,4-dihydro-1-methylamino-4-oxo-3-quinolinecarboxylic acid, mp 222°-224° C.

Workup

  1. temperatureThe mixture was refluxed for one hour
  2. filtrationThe solids were filtered

Sources & evidence

ORD record
ord-d4243b90e472472d9a9a7051be655a9a
Source dataset
uspto-grants-1986_08
Patent number
US04604401

Reaction notes

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