Triethylamine → 1-Cyclopropyl-6-fluoro-7-(3-amino-1-azetidinyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

HRID 1651413Notes

Reaction equation

HRID 1651413 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:15])=[C:11](F)[CH:12]=3)[C:7](=[O:16])[C:6]([C:17]([OH:19])=[O:18])=[CH:5]2)[CH2:3][CH2:2]1.Cl.[NH2:21][CH:22]1[CH2:25][NH:24][CH2:23]1.C(N(CC)CC)C>N1C=CC=CC=1>[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:15])=[C:11]([N:24]4[CH2:25][CH:22]([NH2:21])[CH2:23]4)[CH:12]=3)[C:7](=[O:16])[C:6]([C:17]([OH:19])=[O:18])=[CH:5]2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 52104221-Cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acidHCID 23051791Azetidin-3-amine hydrochloride

Product 1

HCID 100871801-Cyclopropyl-6-fluoro-7-(3-amino-1-azetidinyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylic acidYield 58%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 1.2 g (4.53 mmoles) of 1-cyclopropyl 6,7-difluoro-1,4-dihydro-4oxo-3-quinolinecarboxylic acid, 1.3 g (9.05 mmoles) of 3-aminoazetidine hydrochloride and 0.5 ml of triethylamine heated in 15 ml of pyridine for 2 hours. The mixture is filtrated and washed with water and ethanol to obtain 0.83 g (58%) of 1-cyclopropyl-6-fluoro-7-(3-amino-1-azetidinyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid melting at 246°-7° C.

Workup

  1. filtrationThe mixture is filtrated
  2. washwashed with water and ethanol

Sources & evidence

ORD record
ord-f8b96e2e5c9442d6b96b5a65602cf713
Source dataset
uspto-grants-1990_05
Patent number
US04927926

Reaction notes

Loading…