Ethyl-pyrrolidin-3-ylmethyl-amine → HCID 461888, compound

HRID 978540Notes

Reaction equation

HRID 978540 reaction equation
[CH:1]1([N:6]2[C:15]3[C:10](=[CH:11][C:12]([F:18])=[C:13](F)[C:14]=3[F:16])[C:9](=[O:19])[C:8]([C:20]([OH:22])=[O:21])=[CH:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:23]([NH:25][CH2:26][CH:27]1[CH2:31][CH2:30][NH:29][CH2:28]1)[CH3:24]>C(#N)C>[CH:1]1([N:6]2[C:15]3[C:10](=[CH:11][C:12]([F:18])=[C:13]([N:29]4[CH2:30][CH2:31][CH:27]([CH2:26][NH:25][CH2:23][CH3:24])[CH2:28]4)[C:14]=3[F:16])[C:9](=[O:19])[C:8]([C:20]([OH:22])=[O:21])=[CH:7]2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 2

HCID 13491786Ethyl-pyrrolidin-3-ylmethyl-amineHCID 13772833HCID 13772833, compound

Product 1

HCID 461888HCID 461888, compoundYield 74.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To 0.86 g (2.7 mmol) of the 1-cyclopentyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid in 10 ml of acetonitrile was added 0.40 g (2.7 mmol) of 1,8-diazobicyclo [5.4.0] undec-7-ene and 0.36 g (2.7 mmol) of 3-[(ethylamino)methyl]pyrrolidine. The mixture was refluxed for seven hours, cooled, filtered, and the solids washed with ether to give 0.84 g of 1-cyclopentyl-7-[3-[(ethylamino)methyl]-1-pyrrolidinyl]-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic-acid, mp 214°-217° C.

Workup

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

Sources & evidence

ORD record
ord-d889d904129d47308cd532b8b4c6d075
Source dataset
uspto-grants-1987_05
Patent number
US04665079

Reaction notes

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