Ethyl-pyrrolidin-3-ylmethyl-amine → HCID 13772806, compound

HRID 868084Notes

Reaction equation

HRID 868084 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([F:13])[C:11]=1F)[N:8]([CH:14]1[CH2:16][CH:15]1[CH3:17])[CH:7]=[C:6]([C:18]([OH:20])=[O:19])[C:5]2=[O:21].[CH2:22]([NH:24][CH2:25][CH:26]1[CH2:30][CH2:29][NH:28][CH2:27]1)[CH3:23]>C(#N)C>[CH2:22]([NH:24][CH2:25][CH:26]1[CH2:30][CH2:29][N:28]([C:11]2[C:10]([F:13])=[C:9]3[C:4]([C:5](=[O:21])[C:6]([C:18]([OH:20])=[O:19])=[CH:7][N:8]3[CH:14]3[CH2:16][CH:15]3[CH3:17])=[CH:3][C:2]=2[F:1])[CH2:27]1)[CH3:23]

Participants

4

Reactant 2

HCID 13491786Ethyl-pyrrolidin-3-ylmethyl-amineHCID 13772830HCID 13772830, compound

Product 1

HCID 13772806HCID 13772806, compoundYield 80.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To 0.75 g (2.57 mmol) of 6,7,8-trifluoro-1,4-dihydro-1-(2-methylcyclopropyl)-4-oxo-3-quinolinecarboxylic acid in 15 ml of acetonitrile was added 0.38 g (2.57 mmol) of 1,8-diazobicyclo[5.4.0]undec-7-ene and 0.32 g (2.57 mmol) of 3-[(ethylamino)methyl]pyrrolidine. The mixture was refluxed for two hours, cooled, filtered, and the solids washed with ether to give 0.84 g of 7-[3-[(ethylamino)methyl]-1-pyrrolidinyl]-6,8-difluoro-1,4-dihydro-1-(2-methylcyclopropyl)-4-oxo-3-quinolinecarboxylic acid, mp 225°-228° C.

Workup

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

Sources & evidence

ORD record
ord-dbbd261ec9d24a2f938d2e39c6e3558b
Source dataset
uspto-grants-1988_10
Patent number
US04777175

Reaction notes

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