Ammonia methanol → 2-(4-{5-Fluoro-1-[(2-morpholin-4-yl-ethylcarbamoyl)methyl]-4-oxo-8-propoxy-1,4-dihydroquinolin-3-yl}phenoxy)acetamide

HRID 68165Notes

Reaction equation

HRID 68165 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:41])[C:5]([C:28]1[CH:40]=[CH:39][C:31]([O:32][CH2:33][C:34]([O:36]CC)=O)=[CH:30][CH:29]=1)=[CH:6][N:7]2[CH2:16][C:17](=[O:27])[NH:18][CH2:19][CH2:20][N:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1.[NH3:42].CO>>[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:41])[C:5]([C:28]1[CH:29]=[CH:30][C:31]([O:32][CH2:33][C:34]([NH2:42])=[O:36])=[CH:39][CH:40]=1)=[CH:6][N:7]2[CH2:16][C:17](=[O:27])[NH:18][CH2:19][CH2:20][N:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1

Participants

3

Reactant 2

HCID 21705897Ammonia methanolHCID 68207144Ethyl (4-{5-fluoro-1-[(2-morpholin-4-yl-ethylcarbamoyl)methyl]-4-oxo-8-propoxy-1,4-dihydroquinolin-3-yl}phenoxy)acetate

Product 1

HCID 674632762-(4-{5-Fluoro-1-[(2-morpholin-4-yl-ethylcarbamoyl)methyl]-4-oxo-8-propoxy-1,4-dihydroquinolin-3-yl}phenoxy)acetamideYield 35%

Conditions

Temperature
70 °C

Procedure

Ethyl (4-{5-fluoro-1-[(2-morpholin-4-yl-ethylcarbamoyl)methyl]-4-oxo-8-propoxy-1,4-dihydroquinolin-3-yl}phenoxy)acetate (300 mg) was added to a 7N ammonia-methanol solution (15 ml) and then stirred at 70° C. for 43 hours. The mixture was cooled to room temperature and concentrated under reduced pressure. The residue was purified using silica gel column chromatography (dichloromethane:methanol=50:19:1→ethyl acetate:methanol=10:1). The purified product was concentrated under reduced pressure, and the residue was recrystallized from ethyl acetate-n-hexane, giving a pale yellow powder of 2-(4-{5-fluoro-1-[(2-morpholin-4-yl-ethylcarbamoyl)methyl]-4-oxo-8-propoxy-1,4-dihydroquinolin-3-yl}phenoxy)acetamide (100 mg, yield: 35%)

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified
  4. concentrationThe purified product was concentrated under reduced pressure
  5. customthe residue was recrystallized from ethyl acetate-n-hexane

Sources & evidence

ORD record
ord-ed9d1b45c4b1447c9961dc973407a08d
Source dataset
uspto-grants-2014_09
Patent number
USRE045108E1

Reaction notes

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