Pyridine → HCID 10245432, compound

HRID 1651392Notes

Reaction equation

HRID 1651392 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.[NH:21]1[CH2:24][CH2:23][CH2:22]1.N1C=CC=CC=1>C(N(CC)CC)C>[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:16])=[C:11]([N:21]4[CH2:24][CH2:23][CH2:22]4)[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

Participants

5

Reactant 3

HCID 1049PyridineHCID 10422AzetidineHCID 5354141-Cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Product 1

HCID 10245432HCID 10245432, compoundYield 89.2%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A mixture of 0.6 g (2.1 mmoles) of 1-cyclopropyl-1,4-dihydro-6,7,8-trifluoro-4-oxo-3-quinolinecarboxylic acid with 0.25 g (4.4 mmoles) of azetidine, 8 ml of pyridine and 1 ml of triethylamine is maintained at 110°-120° C. for 2 hours in a closed vessel. After cooling, evaporating under vacuum, filtering and washing, 0.6 g (88%) of 1-cyclopropyl-6,8-difluoro-1,4-dihydro-7-(1-azetidinyl)-4-oxo-3-quinolinecarboxylic acid are obtained, melting at 289°-93° C.

Workup

  1. temperatureis maintained at 110°-120° C. for 2 hours in a closed vessel
  2. temperatureAfter cooling
  3. customevaporating under vacuum
  4. filtrationfiltering
  5. washwashing

Sources & evidence

ORD record
ord-9983511eb09442faad7ebc91b068cc7f
Source dataset
uspto-grants-1990_05
Patent number
US04927926

Reaction notes

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