Dichloromethane → 2-chloro-N-{3-[5-fluoro-3-(4-methoxyphenyl)-4-oxo-8-propoxy-4H-quinolin-1-yl]propyl}acetamide

HRID 68153Notes

Reaction equation

HRID 68153 reaction equation
ClCCl.[NH2:4][CH2:5][CH2:6][CH2:7][N:8]1[C:17]2[C:12](=[C:13]([F:22])[CH:14]=[CH:15][C:16]=2[O:18][CH2:19][CH2:20][CH3:21])[C:11](=[O:23])[C:10]([C:24]2[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=2)=[CH:9]1.C(N(CC)CC)C.[Cl:39][CH2:40][C:41](Cl)=[O:42]>O>[Cl:39][CH2:40][C:41]([NH:4][CH2:5][CH2:6][CH2:7][N:8]1[C:17]2[C:12](=[C:13]([F:22])[CH:14]=[CH:15][C:16]=2[O:18][CH2:19][CH2:20][CH3:21])[C:11](=[O:23])[C:10]([C:24]2[CH:25]=[CH:26][C:27]([O:30][CH3:31])=[CH:28][CH:29]=2)=[CH:9]1)=[O:42]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 584925271-(3-aminopropyl)-5-fluoro-3-(4-methoxyphenyl)-8-propoxy-1H-quinolin-4-one

Product 1

HCID 584925612-chloro-N-{3-[5-fluoro-3-(4-methoxyphenyl)-4-oxo-8-propoxy-4H-quinolin-1-yl]propyl}acetamideYield 48.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A dichloromethane solution (6 ml) of 1-(3-aminopropyl)-5-fluoro-3-(4-methoxyphenyl)-8-propoxy-1H-quinolin-4-one (645 mg, 1.67 mmol) was ice-cooled. Triethylamine (253 mg, 2.5 mmol) and chloroacetyl chloride (207 mg, 1.83 mmol) were added to the solution and stirred at room temperature for 2 hours. Water was added to the reaction mixture, followed by extraction using dichloromethane. The thus-obtained organic layer was condensed, and the residue was then purified using silica gel column chromatography (dichloromethane:ethyl acetate=4:1→2:1). The purified product was concentrated to dryness under reduced pressure, giving a white powder of 2-chloro-N-{3-[5-fluoro-3-(4-methoxyphenyl)-4-oxo-8-propoxy-4H-quinolin-1-yl]propyl}acetamide (372 mg, yield: 48%).

Workup

  1. temperaturecooled
  2. extractionfollowed by extraction
  3. customcondensed
  4. customthe residue was then purified
  5. concentrationThe purified product was concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-dea0daddd6294d0ca8a3098e14ce3d5a
Source dataset
uspto-grants-2014_09
Patent number
USRE045108E1

Reaction notes

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