Triethylamine → HCID 59002973, compound

HRID 561116Notes

Reaction equation

HRID 561116 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[C:9]([F:17])[C:10]([F:16])=[C:11](F)[C:12]=3[F:14])[C:7](=[O:18])[C:6]([C:19]([OH:21])=[O:20])=[CH:5]2)[CH2:3][CH2:2]1.[N:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[NH:28][CH2:29][CH2:30][NH2:31].C(N(CC)CC)C>CCO>[CH:1]1([N:4]2[C:13]3[C:8](=[C:9]([F:17])[C:10]([F:16])=[C:11]([NH:31][CH2:30][CH2:29][NH:28][C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][N:22]=4)[C:12]=3[F:14])[C:7](=[O:18])[C:6]([C:19]([OH:21])=[O:20])=[CH:5]2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 410428N~1~-(Pyridin-2-yl)ethane-1,2-diamineHCID 138255151-Cyclopropyl-5,6,7,8-tetrafluoro-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid

Product 1

HCID 59002973HCID 59002973, compoundYield 56.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 1-cyclopropyl-5,6,7,8-tetrafluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (3.70 g, 12.3 mmol), N-2-pyridyl-1,2-ethanediamine (1.77 g, 12.9 mmol) and triethylamine (3.50 mL) in EtOH (50 mL) was stirred at room temperature for 3 h, and refluxed for 1 h. The reaction mixture was cooled at room temperature. The resulting precipitate was combined by filtration. The cake washed with EtOH and collected by filtration and then dried to give 1-cyclopropyl-1,4-dihydro-5,6,8-trifluoro-4-oxo-7-[2-(2-pyridylamino)ethylamino]quinoline-3-carboxylic acid (2.90 g, 56%) as a pale yellow solid.

Workup

  1. temperaturerefluxed for 1 h
  2. filtrationThe resulting precipitate was combined by filtration
  3. washThe cake washed with EtOH
  4. filtrationcollected by filtration
  5. customdried

Sources & evidence

ORD record
ord-ae7811466e6f404488cc7d51c399fe94
Source dataset
uspto-grants-2011_11
Patent number
US08063221B2

Reaction notes

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