Triethylamine → HCID 24754258, compound

HRID 561167Notes

Reaction equation

HRID 561167 reaction equation
[NH2:1][C:2]1[C:11]([F:12])=[C:10](F)[C:9]([O:14][CH:15]([CH3:17])[CH3:16])=[C:8]2[C:3]=1[C:4](=[O:24])[C:5]([C:21]([OH:23])=[O:22])=[CH:6][N:7]2[CH:18]1[CH2:20][CH2:19]1.[N:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[NH:31][CH2:32][CH2:33][NH2:34].C(N(CC)CC)C.[NH4+].[Cl-]>CS(C)=O>[NH2:1][C:2]1[C:11]([F:12])=[C:10]([NH:34][CH2:33][CH2:32][NH:31][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][N:25]=2)[C:9]([O:14][CH:15]([CH3:16])[CH3:17])=[C:8]2[C:3]=1[C:4](=[O:24])[C:5]([C:21]([OH:23])=[O:22])=[CH:6][N:7]2[CH:18]1[CH2:19][CH2:20]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 410428N~1~-(Pyridin-2-yl)ethane-1,2-diamineHCID 59002961HCID 59002961, compound

Product 1

HCID 24754258HCID 24754258, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 5-amino-1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-isopropoxy-4-oxoquinoline-3-carboxylic acid (100 mg, 0.296 mmol), N-2-pyridyl-1,2-ethanediamine (60.9 mg, 0.444 mmol) and triethylamine (0.0619 mL, 0.444 mmol) in DMSO (3 mL) was stirred at 100° C. for 8 h. After the reaction mixture was poured into ice-water, NH4Cl was added and stirred for 30 min. The resulting precipitate was collected by filtration in vacuo and washed with water. The crude product was purified by preparative thin layer chromatography (Hexane:EtOAc 1:4) to yield 5-amino-1-cyclopropyl-6-fluoro-1,4-dihydro-8-isopropoxy-4-oxo-7-[2-(2-pyridylamino)ethylamino]quinoline-3-carboxylic acid (80.6 mg, 60%) as a pale yellow amorphous solid.

Workup

  1. additionwas added
  2. filtrationThe resulting precipitate was collected by filtration in vacuo
  3. washwashed with water
  4. customThe crude product was purified by preparative thin layer chromatography (Hexane:EtOAc 1:4)

Sources & evidence

ORD record
ord-e385721bd13c46c696ae4fdcd5ec00c0
Source dataset
uspto-grants-2011_11
Patent number
US08063221B2

Reaction notes

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