Morpholine → 1-(5-morpholin-4-yl-5-oxopentyl)-2-propyl-1H-imidazo[4,5-c]quinoline

HRID 2366683Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2366683
[CH2:1]([C:4]1[N:5]([CH2:17][CH2:18][CH2:19][CH2:20][C:21](O)=[O:22])[C:6]2[C:15]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[N:9]=[CH:8][C:7]=2[N:16]=1)[CH2:2][CH3:3].C(Cl)(=O)C(Cl)=O.[NH:30]1[CH2:35][CH2:34][O:33][CH2:32][CH2:31]1>>[N:30]1([C:21](=[O:22])[CH2:20][CH2:19][CH2:18][CH2:17][N:5]2[C:6]3[C:15]4[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=4[N:9]=[CH:8][C:7]=3[N:16]=[C:4]2[CH2:1][CH2:2][CH3:3])[CH2:35][CH2:34][O:33][CH2:32][CH2:31]1

Komponenten

4

Edukt 3

HCID 8083Morpholine2×HCID 65578Oxalyl chloride2×HCID 574470705-(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)pentanoic acid

Produkt 1

HCID 695067201-(5-morpholin-4-yl-5-oxopentyl)-2-propyl-1H-imidazo[4,5-c]quinolineAusbeute 98,8 %

Versuchsvorschrift

A modification of the method described in Part F of Example 6 was used to treat 5-(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)pentanoic acid (5.14 g, 16.5 mmol) with oxalyl chloride (2.59 mL, 29.7 mmol) and morpholine (4.33 mL, 49.5 mmol). The oxalyl chloride addition was carried out at ambient temperature, and the reaction with morpholine was complete in three hours. Following the work-up procedure, 6.2 g of 1-(5-morpholin-4-yl-5-oxopentyl)-2-propyl-1H-imidazo[4,5-c]quinoline were obtained.

Aufarbeitung

  1. customwas carried out at ambient temperature

Quellen und Nachweise

ORD-Eintrag
ord-63aafa9d1ab84116925eccc58bdf3dac
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08697873B2

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