Triphenylphosphine → 1-methyl-4-{3-[(2-pyridin-3-ylethyl)pyridin-4-ylmethylamino]propoxy}-1H-quinolin-2-one trihydrochloride

HRID 69006Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 69006
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.[OH:32][C:33]1[C:42]2[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=2)[N:36]([CH3:43])[C:35](=[O:44])[CH:34]=1.[N:45]1[CH:50]=[CH:49][CH:48]=[C:47]([CH2:51][CH2:52][N:53]([CH2:58][C:59]2[CH:64]=[CH:63][N:62]=[CH:61][CH:60]=2)[CH2:54][CH2:55][CH2:56]O)[CH:46]=1.C(OC(=O)C)C.[ClH:71]>C(OCC)(=O)C.O1CCCC1>[ClH:71].[ClH:71].[ClH:71].[CH3:43][N:36]1[C:37]2[C:42](=[CH:41][CH:40]=[CH:39][CH:38]=2)[C:33]([O:32][CH2:56][CH2:55][CH2:54][N:53]([CH2:52][CH2:51][C:47]2[CH:46]=[N:45][CH:50]=[CH:49][CH:48]=2)[CH2:58][C:59]2[CH:64]=[CH:63][N:62]=[CH:61][CH:60]=2)=[CH:34][C:35]1=[O:44]

Komponenten

8

Edukt 5

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 21866389Hydrogen chloride-ethyl acetateHCID 546864364-Hydroxy-N-methylcarbostyrilHCID 669609373-[(2-Pyridin-3-ylethyl)pyridin-4-ylmethylamino]propan-1-ol

Produkt 1

HCID 706566631-methyl-4-{3-[(2-pyridin-3-ylethyl)pyridin-4-ylmethylamino]propoxy}-1H-quinolin-2-one trihydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Triphenyl phosphine (102 mg) and diethyl azodicarboxylate (68 mg) were added to a tetrahydrofuran (THF) solution (5 ml) of 4-hydroxy-1-methyl-1H-quinolin-2-one (63 mg), and 3-[(2-pyridin-3-ylethyl)pyridin-4-ylmethylamino]propane-1-ol (81.4 mg). The mixture was stirred overnight. After the reaction mixture was condensed under reduced pressure, the residue was purified by silica gel column chromatography (dichloromethane:methanol=20:1→10:1). The purified product was condensed under reduced pressure. A 4N-hydrogen chloride ethyl acetate solution (0.29 ml) was added to an ethyl acetate solution of the residue, which was stirred at room temperature for 30 minutes. The generated insoluble matter was separated by filtration, and dried to give the title compound (126.8 mg) as a white powder.

Aufarbeitung

  1. customcondensed under reduced pressure
  2. customthe residue was purified by silica gel column chromatography (dichloromethane:methanol=20:1→10:1)
  3. customcondensed under reduced pressure
  4. stirringwas stirred at room temperature for 30 minutes
  5. customThe generated insoluble matter was separated by filtration
  6. customdried

Quellen und Nachweise

ORD-Eintrag
ord-d469d05a921c4350ab72b6b815abcf9f
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822453B2

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