Morpholine → HCID 66917331, compound

HRID 2388125Notes

Reaction equation

HRID 2388125 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH2:14][CH3:15])=[C:8]2[C:3]=1[C:4](=[O:25])[C:5]([C:16]1[CH:24]=[CH:23][C:19]([C:20](O)=[O:21])=[CH:18][CH:17]=1)=[CH:6][NH:7]2.[NH:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C>[F:1][C:2]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH2:14][CH3:15])=[C:8]2[C:3]=1[C:4](=[O:25])[C:5]([C:16]1[CH:17]=[CH:18][C:19]([C:20]([N:26]3[CH2:31][CH2:30][O:29][CH2:28][CH2:27]3)=[O:21])=[CH:23][CH:24]=1)=[CH:6][NH:7]2

Participants

6

Reactant 4

HCID 8083MorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 66917237HCID 66917237, compound

Product 1

HCID 66917331HCID 66917331, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-(5-Fluoro-4-oxo-8-propoxy-1,4-dihydroquinolin-3-yl)benzoic acid (260 mg, 0.76 mmol), morpholine (99.5 mg, 1.14 mmol), WSC (189 mg, 0.99 mmol) and HOBT (151 mg, 0.99 mmol) were added to DMF (10 ml), and the mixture was stirred at room temperature for 15 hours. The reaction mixture was concentrated under reduced pressure, and the residue was then purified by silica gel column chromatography (dichloromethane:methanol=30:1). The purified product was concentrated under reduced pressure, and the residue was recrystallized from ethyl acetate to thereby obtain 80 mg of powdery white 5-fluoro-3-[4-(morpholine-4-carbonyl)phenyl]-8-propoxy-1H-quinolin-4-one (yield: 26%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was then purified by silica gel column chromatography (dichloromethane:methanol=30:1)
  3. concentrationThe purified product was concentrated under reduced pressure
  4. customthe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-0fe6315e20be44809afc7f642c584ff5
Source dataset
uspto-grants-2012_09
Patent number
US08269011B2

Reaction notes

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