1-Hydroxybenzotriazole → 2-[5-fluoro-3-(4-hydroxyphenyl)-4-oxo-8-propoxy-4H-quinolin-1-yl]-N-(2-morpholin-4-ylethyl)acetamide

HRID 68164Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 68164
[NH2:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][O:7][CH2:6][CH2:5]1.Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.[F:32][C:33]1[CH:42]=[CH:41][C:40]([O:43][CH2:44][CH2:45][CH3:46])=[C:39]2[C:34]=1[C:35](=[O:58])[C:36]([C:51]1[CH:56]=[CH:55][C:54]([OH:57])=[CH:53][CH:52]=1)=[CH:37][N:38]2[CH2:47][C:48](O)=[O:49]>C(N(CC)CC)C.O.CN(C=O)C>[F:32][C:33]1[CH:42]=[CH:41][C:40]([O:43][CH2:44][CH2:45][CH3:46])=[C:39]2[C:34]=1[C:35](=[O:58])[C:36]([C:51]1[CH:52]=[CH:53][C:54]([OH:57])=[CH:55][CH:56]=1)=[CH:37][N:38]2[CH2:47][C:48]([NH:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][O:7][CH2:6][CH2:5]1)=[O:49]

Komponenten

8

Edukt 4

HCID 757711-HydroxybenzotriazoleHCID 4082852-MorpholinoethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 58492574[5-fluoro-3-(4-hydroxyphenyl)-4-oxo-8-propoxy-4H-quinolin-1-yl]acetic acid

Produkt 1

HCID 674164372-[5-fluoro-3-(4-hydroxyphenyl)-4-oxo-8-propoxy-4H-quinolin-1-yl]-N-(2-morpholin-4-ylethyl)acetamideAusbeute 24 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

4-(2-Aminoethyl)morpholine (184 mg, 1.41 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (WSC, 295 mg, 1.54 mmol) and 1-hydroxybenzotriazole (HOBT, 215 mg, 1.41 mmol) were added to a DMF solution (7 ml) of [5-fluoro-3-(4-hydroxyphenyl)-4-oxo-8-propoxy-4H-quinolin-1-yl]acetic acid (500 mg, 1.34 mmol) and then the mixture was stirred at room temperature for 23 hours. Water and triethylamine were added to the reaction mixture to make the reaction mixture basic, followed by extraction using ethyl acetate. The thus-obtained organic layer was washed with an aqueous saturated sodium chloride solution, and then concentrated under reduced pressure. The residue was purified using silica gel column chromatography (dichloromethane:methanol=30:1→10:1). The purified product was concentrated under reduced pressure, and the residue was recrystallized from ethyl acetate, giving a white powder of 2-[5-fluoro-3-(4-hydroxyphenyl)-4-oxo-8-propoxy-4H-quinolin-1-yl]-N-(2-morpholin-4-ylethyl)acetamide (157 yield: 24%).

Aufarbeitung

  1. extractionfollowed by extraction
  2. washThe thus-obtained organic layer was washed with an aqueous saturated sodium chloride solution
  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

Quellen und Nachweise

ORD-Eintrag
ord-5b8b76da6a92400cbbe71c99a9529cfc
Quelldatensatz
uspto-grants-2014_09
Patentnummer
USRE045108E1

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