Triethylamine → HCID 19106852, compound

HRID 1197492Notes

Reaction equation

HRID 1197492 reaction equation
[NH2:1][C:2]1[C:11]([F:12])=[C:10](F)[C:9]([F:14])=[C:8]2[C:3]=1[C:4](=[O:21])[C:5]([C:18]([OH:20])=[O:19])=[CH:6][N:7]2[CH:15]1[CH2:17][CH2:16]1.[OH:22][N:23]=[C:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1.FC(F)(F)C([O-])=O.C(N(CC)CC)C>CS(C)=O>[NH2:1][C:2]1[C:11]([F:12])=[C:10]([N:27]2[CH2:28][CH2:29][C:24](=[N:23][OH:22])[CH2:25][CH2:26]2)[C:9]([F:14])=[C:8]2[C:3]=1[C:4](=[O:21])[C:5]([C:18]([OH:20])=[O:19])=[CH:6][N:7]2[CH:15]1[CH2:16][CH2:17]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 139109475-Amino-1-cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 86747460HCID 86747460, compound

Product 1

HCID 19106852HCID 19106852, compoundYield 38.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
80 °C

Procedure

298 mg (1 mmol) of 5-amino-1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid was dissolved in 5 ml of dimethyl sulfoxide, and 570 mg (2.5 mmol) of 4-hydroxyiminopiperidine-trifluoroacetate and 404 mg (4 mmol) of triethylamine were added thereto. The mixture was stirred at 80° C. for 6 hours. After cooling, the precipitate thereby formed was collected by filtration and washed with water, isopropanol and diethyl ether to give 150 mg of the desired product as yellow powder.

Workup

  1. temperatureAfter cooling
  2. customthe precipitate thereby formed
  3. filtrationwas collected by filtration
  4. washwashed with water, isopropanol and diethyl ether

Sources & evidence

ORD record
ord-06f0d7a2d9f2469295dd733239511d98
Source dataset
uspto-grants-1994_01
Patent number
US05276041

Reaction notes

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