1-Cyclopropyl-5,6,7,8-tetrafluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid → HCID 14304608, compound

HRID 477019Notes

Reaction equation

HRID 477019 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[C:9]([F:17])[C:10]([F:16])=[C:11](F)[C:12]=3[F:14])[C:7](=[O:18])[C:6]([C:19]([OH:21])=[O:20])=[CH:5]2)[CH2:3][CH2:2]1.[F:22][C:23]([F:35])([F:34])[C:24]([NH:26][C@H:27]1[C@@H:31]([CH2:32][F:33])[CH2:30][NH:29][CH2:28]1)=[O:25]>N1C=CC=CC=1>[CH:1]1([N:4]2[C:13]3[C:8](=[C:9]([F:17])[C:10]([F:16])=[C:11]([N:29]4[CH2:30][C@H:31]([CH2:32][F:33])[C@H:27]([NH:26][C:24](=[O:25])[C:23]([F:35])([F:34])[F:22])[CH2:28]4)[C:12]=3[F:14])[C:7](=[O:18])[C:6]([C:19]([OH:21])=[O:20])=[CH:5]2)[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 138255151-Cyclopropyl-5,6,7,8-tetrafluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 15729377HCID 15729377, compound

Product 1

HCID 14304608HCID 14304608, compoundYield 57.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 1-cyclopropyl-5,6,7,8-tetrafluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (1.32 g), cis-3-trifluoroacetylamino-4-fluoromethylpyrrolidine (1.41 g), and pyridine (10 ml) was refluxed for 5 hours. The reaction mixture was concentrated to dryness under reduced pressure. Water was added to the residue, and the resulting precipitate were collected. Recrystallization from dimethylformamide gave 1-cyclopropyl-5,6,8-trifluoro-7-(cis-3-trifluoroacetylamino-4-fluoromethyl-1-pyrrolidinyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (1.25 g), m.p. 283°-284° C.

Workup

  1. temperaturewas refluxed for 5 hours
  2. concentrationThe reaction mixture was concentrated to dryness under reduced pressure
  3. additionWater was added to the residue
  4. customthe resulting precipitate were collected
  5. customRecrystallization from dimethylformamide

Sources & evidence

ORD record
ord-9e16f355a5e248d29d1a4b9c743a8bdc
Source dataset
uspto-grants-1989_12
Patent number
US04886810

Reaction notes

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