Dabco → HCID 13850785, compound

HRID 1382209Notes

Reaction equation

HRID 1382209 reaction equation
N12CCN(CC1)CC2.[CH:9]1([N:12]2[C:21]3[C:16](=[CH:17][C:18]([F:23])=[C:19](F)[CH:20]=3)[C:15](=[O:24])[C:14]([C:25]([OH:27])=[O:26])=[CH:13]2)[CH2:11][CH2:10]1.Cl.Cl.[C:30]([N:34]1[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]1)([CH3:33])([CH3:32])[CH3:31]>N1C=CC=CC=1>[C:30]([N:34]1[CH2:39][CH2:38][N:37]([C:19]2[CH:20]=[C:21]3[C:16]([C:15](=[O:24])[C:14]([C:25]([OH:27])=[O:26])=[CH:13][N:12]3[CH:9]3[CH2:11][CH2:10]3)=[CH:17][C:18]=2[F:23])[CH2:36][CH2:35]1)([CH3:33])([CH3:32])[CH3:31]

Participants

5

Reactant 3

HCID 9237DabcoHCID 52104221-Cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acidHCID 21274491HCID 21274491, compound

Product 1

HCID 13850785HCID 13850785, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2.2 g (20 mmol) of 1,4-diazabicyclo[2,2,2]octane are added to a mixture of 1.33 g (5 mmol) of 1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid and 1.1 g (5 mmol) of 1-(tert.-butyl)piperazine dihydrochloride in 12.5 ml of pyridine, and the mixture is heated under reflux for 3 hours. It is concentrated in vacuo, the residue is stirred with 25 ml of water and the pH is brought to 5 with 2N hydrochloric acid. The precipitate which has separated out is filtered off with suction, washed with water and recrystallized from glycol monomethyl ether. 1.45 g (75% of theory) of 7-(4-tert.-butyl-1-piperazinyl)-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid of melting point 257°-260° are obtained.

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for 3 hours
  3. concentrationIt is concentrated in vacuo
  4. customThe precipitate which has separated out
  5. filtrationis filtered off with suction
  6. washwashed with water
  7. customrecrystallized from glycol monomethyl ether

Sources & evidence

ORD record
ord-90d211d7317843aa9dcb6aa2ab51e963
Source dataset
uspto-grants-1989_02
Patent number
US04806539

Reaction notes

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