Triethylamine → HCID 59002828, compound

HRID 561142Notes

Reaction equation

HRID 561142 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])[CH:6]=[C:5]2[C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:3][CH2:2]1.[N:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[NH:30][CH2:31][CH2:32][NH2:33].C(N(CC)CC)C>CS(C)=O>[CH:1]1([N:4]2[C:13]3[C:8](=[C:9]([F:17])[C:10]([F:16])=[C:11]([NH:33][CH2:32][CH2:31][NH:30][C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][N:24]=4)[C:12]=3[F:14])[C:7](=[O:18])[CH:6]=[C:5]2[C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 410428N~1~-(Pyridin-2-yl)ethane-1,2-diamineHCID 59002982HCID 59002982, compound

Product 1

HCID 59002828HCID 59002828, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution ethyl 1-cyclopropyl-5,6,7,8-tetrafluoro-1,4-dihydro-4-oxoquinoline-2-carboxylate (688 mg, 2.09 mmol), N-2-pyridyl-1,2-ethanediamine (570 mg, 4.16 mmol) and triethylamine (0.87 mL, 6.24 mmol) in DMSO (20 mL) was stirred at 70° C. After 1 h, the reaction mixture was poured into ice water and the resulting solution was extracted with EtOAc, and the organic layer washed with water, brine, and then dried. The solvent was removed and the crude product was purified by column chromatography (Hexane:EtOAc 1:1) to yield ethyl 1-cyclopropyl-5,6,8-trifluoro-1,4-dihydro-4-oxo-7-[2-(2-pyridylamino)ethylamino]quinoline-2-carboxylate (773 mg, 83%) as yellow solid.

Workup

  1. extractionthe resulting solution was extracted with EtOAc
  2. washthe organic layer washed with water, brine
  3. customdried
  4. customThe solvent was removed
  5. customthe crude product was purified by column chromatography (Hexane:EtOAc 1:1)

Sources & evidence

ORD record
ord-09ec7b49ed7e474db2618bd624c25d06
Source dataset
uspto-grants-2011_11
Patent number
US08063221B2

Reaction notes

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