Triethylamine → HCID 23051790, compound

HRID 1651401Notes

Reaction equation

HRID 1651401 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]([O:20][CH2:21][CH3:22])=[O:19])=[CH:5]2)[CH2:3][CH2:2]1.Cl.[F:24][C:25]([F:34])([F:33])[C:26]([NH:28][CH:29]1[CH2:32][NH:31][CH2:30]1)=[O:27].C(N(CC)CC)C>CS(C)=O.O>[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:16])=[C:11]([N:31]4[CH2:32][CH:29]([NH:28][C:26](=[O:27])[C:25]([F:34])([F:33])[F:24])[CH2:30]4)[C:12]=3[F:14])[C:7](=[O:17])[C:6]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:5]2)[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 5354151-Cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic Acid Ethyl EsterHCID 19423639N-(Azetidin-3-yl)-2,2,2-trifluoroacetamide--hydrogen chloride (1/1)

Product 1

HCID 23051790HCID 23051790, compoundYield 22%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

A mixture of 1 g (3.2 mmoles) of ethyl 1-cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylate, 0.98 g (4.8 mmoles) of 3-trifluoroacetamidoazetidine hydrochloride and 2 ml of triethylamine is heated in 15 ml of dimethyl sulphoxide for 4 hours at 80°-5° C. It is diluted with water and extracted with chloroform. The organic phase is washed with water and evaporated yielding 0.31 g (22% of ethyl 1-cyclopropyl-6,8-difluoro-1,4-dihydro-7-(3-trifluoroacetamido-1-azetidinyl)-4-oxo-3-quinolinecarboxylate which is then hydrolysed by heating a mixture of 0.1 g (0.22 mmoles) of this ester with 5 ml of 1N sodium hydroxide and 5 ml of ethanol. The mixture is cooled, evaporated and acidified with acetic acid. Filtering and washing with water yields 70 mg (96%) of 1-cyclopropyl-6,8-difluoro-7-(3-amino-1-azetidinyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, melting at 214°-6° C.

Workup

  1. extractionextracted with chloroform
  2. washThe organic phase is washed with water
  3. customevaporated

Sources & evidence

ORD record
ord-9fc0a95954c8475fa3dad6a8b919916d
Source dataset
uspto-grants-1990_05
Patent number
US04927926

Reaction notes

Loading…