Pyridine → HCID 10478672, compound

HRID 1651389Notes

Reaction equation

HRID 1651389 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:16])=[C:11](F)[C:12]=3[F:14])[C:7](=[O:17])[C:6]([C:18]([OH:20])=[O:19])=[CH:5]2)[CH2:3][CH2:2]1.Cl.[F:22][C:23]([F:33])([F:32])[C:24]([NH:26][CH2:27][CH:28]1[CH2:31][NH:30][CH2:29]1)=[O:25].N1C=CC=CC=1>C(N(CC)CC)C>[F:33][C:23]([F:22])([F:32])[C:24]([NH:26][CH2:27][CH:28]1[CH2:29][N:30]([C:11]2[C:12]([F:14])=[C:13]3[C:8]([C:7](=[O:17])[C:6]([C:18]([OH:20])=[O:19])=[CH:5][N:4]3[CH:1]3[CH2:2][CH2:3]3)=[CH:9][C:10]=2[F:16])[CH2:31]1)=[O:25]

Participants

5

Reactant 3

HCID 1049PyridineHCID 5354141-Cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 23051792124668-52-6

Product 1

HCID 10478672HCID 10478672, compoundYield 89.8%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A solution of 0.8 g (2.8 mmoles) of 1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, 0.92 g (4.2 mmoles) of 3-trifluoroacetamidomethylazetidine hydrochloride, 8 ml of pyridine and 1.7 g of triethylamine is heated under reflux for 3 hours. It is then evaporated under vacuum, diluted with water and filtered. 1.12 g (88.9%) of 7-(3-trifluoroacetamidomethyl-1-azetidinyl)-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid are obtained, melting at 145°-150° C.

Workup

  1. temperatureunder reflux for 3 hours
  2. customIt is then evaporated under vacuum
  3. additiondiluted with water
  4. filtrationfiltered

Sources & evidence

ORD record
ord-e81376f3c36346749c36bc2eaff7b92e
Source dataset
uspto-grants-1990_05
Patent number
US04927926

Reaction notes

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