1,8-Diazabicyclo(5.4.0)undec-7-ene → 7-[3-[(Ethylamino)methyl]-1-pyrrolidinyl]-6,8-difluoro-1,4-dihydro-1-(1-methylethyl)-4-oxo-3-quinolinecarboxylic Acid

HRID 622526Notes

Reaction equation

HRID 622526 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]([CH3:16])[CH3:15])[CH:7]=[C:6]([C:17]([OH:19])=[O:18])[C:5]2=[O:20].[CH2:21]([NH:23][CH2:24][CH:25]1[CH2:29][CH2:28][NH:27][CH2:26]1)[CH3:22].N12CCCN=C1CCCCC2>C(#N)C>[CH2:21]([NH:23][CH2:24][CH:25]1[CH2:29][CH2:28][N:27]([C:11]2[C:10]([F:13])=[C:9]3[C:4]([C:5](=[O:20])[C:6]([C:17]([OH:19])=[O:18])=[CH:7][N:8]3[CH:14]([CH3:16])[CH3:15])=[CH:3][C:2]=2[F:1])[CH2:26]1)[CH3:22]

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 134776926,7,8-Trifluoro-1,4-dihydro-1-isopropyl-4-oxoquinoline-3-carboxylic acidHCID 13491786Ethyl-pyrrolidin-3-ylmethyl-amine

Product 1

HCID 137728147-[3-[(Ethylamino)methyl]-1-pyrrolidinyl]-6,8-difluoro-1,4-dihydro-1-(1-methylethyl)-4-oxo-3-quinolinecarboxylic AcidYield 73.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 0.57 g (2.0 mmol) of 6,7,8-trifluoro-1,4-dihydro-1-(1-methylethyl)-4-oxo-3-quinolinecarboxylic acid, 0.32 ml (2.2 mmol) of 3-[(ethylamino)methyl]pyrrolidine, 0.30 ml (2.0 mmol) of 1,8-diazabicyclo[5.4.0]undec-7-ene and 15 ml of acetonitrile was heated under reflux for one hour. After cooling to room temperature the mixture was filtered and the solid washed with acetonitrile and methanol to give 0.58 g of the title compound, mp 230°-231° C.

Workup

  1. temperatureunder reflux for one hour
  2. filtrationwas filtered
  3. washthe solid washed with acetonitrile and methanol

Sources & evidence

ORD record
ord-8ea875f6a75e40478acaca9d058ad2c9
Source dataset
uspto-grants-1988_09
Patent number
US04771054

Reaction notes

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