Sulfuric Acid → 2-[6-Methoxy-4-(2-methyl-[1,6]naphthyridin-3-yloxy)-quinolin-7-yloxymethyl]-propane-1,3-diol

HRID 229013Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 229013
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([O:12][C:13]3[C:14]([CH3:23])=[N:15][C:16]4[C:21]([CH:22]=3)=[CH:20][N:19]=[CH:18][CH:17]=4)=[CH:7][CH:8]=[N:9]2)=[CH:4][C:3]=1[O:24][CH3:25].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC1(C)[O:51][CH2:50][CH:49]([CH2:52]O)[CH2:48][O:47]1.S(=O)(=O)(O)O.[OH-].[Na+]>O1CCCC1.O>[CH3:25][O:24][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:2]=1[O:1][CH2:52][CH:49]([CH2:50][OH:51])[CH2:48][OH:47])[N:9]=[CH:8][CH:7]=[C:6]2[O:12][C:13]1[C:14]([CH3:23])=[N:15][C:16]2[C:21]([CH:22]=1)=[CH:20][N:19]=[CH:18][CH:17]=2

Komponenten

8

Edukt 5

HCID 1118Sulfuric AcidHCID 11776TriphenylphosphineHCID 14798Sodium HydroxideHCID 3584869(2,2-Dimethyl-1,3-dioxan-5-yl)methanolHCID 1358548323-(7-Hydroxy-6-methoxy-quinolin-4-yloxy)-2-methyl-[1,6]naphthyridine

Produkt 1

HCID 577565962-[6-Methoxy-4-(2-methyl-[1,6]naphthyridin-3-yloxy)-quinolin-7-yloxymethyl]-propane-1,3-diolAusbeute 63 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

3-(7-Hydroxy-6-methoxy-quinolin-4-yloxy)-2-methyl-[1,6]naphthyridine (85 mg) was dissolved in tetrahydrofuran (2 ml) to prepare a solution. Triphenylphosphine (134 mg), (2,2-dimethyl-[1,3]dioxan-5-yl)-methanol (45 mg), and diethylazodicarboxylic acid (0.1 ml) were added to the solution, and the mixture was stirred at room temperature for 4 hr. Further, 1 N sulfuric acid (4 ml) was added thereto, and the mixture was stirred at room temperature overnight. The reaction solution was brought to 0° C., was stirred, and was made alkaline by the addition of a 10% aqueous sodium hydroxide solution. Water was added thereto, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was then washed with saturated brine and was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by thin layer chromatography using chloroform-methanol to give the title compound (66 mg, yield 63%).

Aufarbeitung

  1. customto prepare a solution
  2. stirringthe mixture was stirred at room temperature overnight
  3. customwas brought to 0° C.
  4. stirringwas stirred
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe ethyl acetate layer was then washed with saturated brine
  7. dry with materialwas dried over anhydrous sodium sulfate
  8. customThe solvent was removed by distillation under the reduced pressure
  9. customthe residue was purified by thin layer chromatography

Quellen und Nachweise

ORD-Eintrag
ord-4f277d5ec8474331bea82d8694a3b904
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07560558B2

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