Ethyl-pyrrolidin-3-ylmethyl-amine → HCID 13728331, compound

HRID 2290521Notes

Reaction equation

HRID 2290521 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([F:13])[C:11]=1F)[N:8]([C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=1)[CH:7]=[C:6]([C:21]([OH:23])=[O:22])[C:5]2=[O:24].[CH2:25]([NH:27][CH2:28][CH:29]1[CH2:33][CH2:32][NH:31][CH2:30]1)[CH3:26]>C(#N)C>[CH2:25]([NH:27][CH2:28][CH:29]1[CH2:33][CH2:32][N:31]([C:11]2[C:10]([F:13])=[C:9]3[C:4]([C:5](=[O:24])[C:6]([C:21]([OH:23])=[O:22])=[CH:7][N:8]3[C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=3)=[CH:3][C:2]=2[F:1])[CH2:30]1)[CH3:26]

Participants

4

Reactant 2

HCID 13491786Ethyl-pyrrolidin-3-ylmethyl-amine2×HCID 137283301-(4-Fluorophenyl)-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

Product 1

HCID 13728331HCID 13728331, compoundYield 87.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To 0.62 g (1.8 mmol) of 6,7,8-trifluoro-1-(4-fluorophenyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid in 15 ml of acetonitrile was added 0.23 g (1.0 equivalent) of N-ethyl-3-pyrrolidinemethanamine and 0.28 g (1.0 equivalent) of 1,8-diazobicyclo [5.4.0]undec-7-ene in 5 ml of acetonitrile. The reaction was refluxed for one hour and then checked by thin layer chromatography. Excess (10%) N-ethyl-3-pyrrolidine methanamine was added as necessary and the mixture heated to reflux for an additional two hours. The solids were then filtered and washed with ether to give 0.70 g of 7-[3-[(ethylamino)methyl]-1-pyrrolidinyl]-6,8-difluoro-1-(4-fluorophenyl)-1,4-dihydro-4-oxo-3-quinoline carboxylic acid, mp 249°-251° C.

Workup

  1. temperatureThe reaction was refluxed for one hour
  2. temperatureheated
  3. temperatureto reflux for an additional two hours
  4. filtrationThe solids were then filtered
  5. washwashed with ether

Sources & evidence

ORD record
ord-c99fb55df50d41358f7174c8ad2c008a
Source dataset
uspto-grants-1986_10
Patent number
US04617308

Reaction notes

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