Potassium Carbonate → HCID 58492597, compound

HRID 1474543Notes

Reaction equation

HRID 1474543 reaction equation
C(=O)([O-])[O-].[K+].[K+].Cl.Cl[CH2:9][CH2:10][N:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1.CN1CCCC1=O.[F:24][C:25]1[CH:34]=[CH:33][C:32]([O:35][CH2:36][CH2:37][CH3:38])=[C:31]2[C:26]=1[C:27](=[O:47])[C:28]([C:39]1[CH:44]=[CH:43][C:42]([O:45][CH3:46])=[CH:41][CH:40]=1)=[CH:29][NH:30]2>C(OCC)(=O)C.O>[F:24][C:25]1[CH:34]=[CH:33][C:32]([O:35][CH2:36][CH2:37][CH3:38])=[C:31]2[C:26]=1[C:27](=[O:47])[C:28]([C:39]1[CH:40]=[CH:41][C:42]([O:45][CH3:46])=[CH:43][CH:44]=1)=[CH:29][N:30]2[CH2:9][CH2:10][N:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 13387N-methyl-2-pyrrolidoneHCID 77210Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)HCID 251656785-fluoro-3-(4-methoxyphenyl)-8-propoxy-1H-quinolin-4-one

Product 1

HCID 58492597HCID 58492597, compoundYield 75.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
55 °C

Procedure

Potassium carbonate (2.1 g, 15.2 mmol) and 4-(2-chloroethyl)morpholine hydrochloride (1.36 g, 7.31 mmol) were added to an N-methylpyrrolidone (NMP) solution (5 ml) of 5-fluoro-3-(4-methoxyphenyl)-8-propoxy-1H-quinolin-4-one (1.0 g, 3.05 mmol) and then stirred at 50 to 60° C. for 45 hours. Water and ethyl acetate were added to the reaction mixture, followed by separation. The thus-obtained organic layer was washed with an aqueous saturated sodium chloride solution twice, and then concentrated under reduced pressure. The residue was purified using silica gel column chromatography (dichloromethane:methanol=50:1→30:1). The purified product was concentrated under reduced pressure, and the residue was recrystallized from ethyl acetate, giving a white powder of 5-fluoro-3-(4-methoxyphenyl)-1-(2-morpholin-4-ylethyl)-8-propoxy-1H-quinolin-4-one (1.01 g, yield: 75%).

Workup

  1. customfollowed by separation
  2. washThe thus-obtained organic layer was washed with an aqueous saturated sodium chloride solution twice
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified
  5. concentrationThe purified product was concentrated under reduced pressure
  6. customthe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-1d8827a176a14d799dfeb63928293342
Source dataset
uspto-grants-2015_04
Patent number
US09018229B2

Reaction notes

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