Trifluoroacetic acid → Ethyl 1-(6-amino-3,5-difluoropyridin-2-yl)-5-benzylamino-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate

HRID 610280Notes

Reaction equation

HRID 610280 reaction equation
[CH2:1]([NH:8][C:9]1[C:18]([F:19])=[C:17]([F:20])[C:16]([F:21])=[C:15]2[C:10]=1[C:11](=[O:45])[C:12]([C:40]([O:42][CH2:43][CH3:44])=[O:41])=[CH:13][N:14]2[C:22]1[C:27]([F:28])=[CH:26][C:25]([F:29])=[C:24]([NH:30]CC2C=CC(OC)=CC=2)[N:23]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>>[NH2:30][C:24]1[N:23]=[C:22]([N:14]2[C:15]3[C:10](=[C:9]([NH:8][CH2:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)[C:18]([F:19])=[C:17]([F:20])[C:16]=3[F:21])[C:11](=[O:45])[C:12]([C:40]([O:42][CH2:43][CH3:44])=[O:41])=[CH:13]2)[C:27]([F:28])=[CH:26][C:25]=1[F:29]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 22121197Ethyl 5-benzylamino-1-[3,5-difluoro-6-(p-methoxybenzylamino)pyridin-2-yl]-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate

Product 1

HCID 22121167Ethyl 1-(6-amino-3,5-difluoropyridin-2-yl)-5-benzylamino-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylateYield 109.4%

Procedure

To 600 mg of ethyl 5-benzylamino-1-[3,5-difluoro-6-(p-methoxybenzylamino)pyridin-2-yl]-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate was added 2 ml of trifluoroacetic acid, and the mixture was allowed to stand at room temperature for 20 minutes. The solution was concentrated under reduced pressure, and 3 ml of ethanol was added to the residue, and the solution was again concentrated under reduced pressure. The precipitate was dispersed in ethanol, collected by filtration and washed with ethanol to obtain 530 mg of the title compound as a yellow powder.

Workup

  1. concentrationThe solution was concentrated under reduced pressure, and 3 ml of ethanol
  2. additionwas added to the residue
  3. concentrationthe solution was again concentrated under reduced pressure
  4. additionThe precipitate was dispersed in ethanol
  5. filtrationcollected by filtration
  6. washwashed with ethanol

Sources & evidence

ORD record
ord-86daa05567f44a4ea6170e2db4d184dc
Source dataset
uspto-grants-1999_12
Patent number
US05998436

Reaction notes

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