Triethylamine → HCID 9980729, compound

HRID 1651405Notes

Reaction equation

HRID 1651405 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.[CH3:21][C:22]1([CH2:26][NH:27][C:28](=[O:33])[C:29]([F:32])([F:31])[F:30])[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][C:22]([CH2:26][NH:27][C:28](=[O:33])[C:29]([F:31])([F:32])[F:30])([CH3:21])[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 14852458133891-75-5

Product 1

HCID 9980729HCID 9980729, compoundYield 91.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 0.7 g (2.6 mmoles) of 1-cyclopropyl-6,7-difluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid, 0.92 g (3.96 mmoles) of 3-methyl-3-trifluoroacetamidomethylazetidine hydrochloride and 1.6 g of triethylamine are heated under reflux for 2 hours in 12 ml of pyridine. The mixture is evaporated, water is added, the product is filtered, and 1.05 g (90%) of 1-cyclopropyl-6-fluoro-7-(3-trifluoroacetamidomethyl-3-methyl-1-azetidinyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid are obtained, melting at 265°-72° C.

Workup

  1. temperatureare heated
  2. customThe mixture is evaporated
  3. additionwater is added
  4. filtrationthe product is filtered

Sources & evidence

ORD record
ord-2265ce8f80464777bc725ac2f537e602
Source dataset
uspto-grants-1990_05
Patent number
US04927926

Reaction notes

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