4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride → 6-[3-(3,4-Dimethyl-benzoyl)-4-oxo-4H-quinolin-1-ylmethyl]-pyridine-2-carboxylic acid amide

HRID 227125

Reaktionsgleichung

Reaktionsgleichung von HRID 227125
Cl.[CH3:2][C:3]1[CH:4]=[C:5]([CH:29]=[CH:30][C:31]=1[CH3:32])[C:6]([C:8]1[C:17](=[O:18])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]([CH2:19][C:20]2[N:25]=[C:24]([C:26](O)=[O:27])[CH:23]=[CH:22][CH:21]=2)[CH:9]=1)=[O:7].[Cl-].COC1N=C(OC)N=C([N+]2(C)CCOCC2)[N:37]=1>CS(C)=O.N>[CH3:2][C:3]1[CH:4]=[C:5]([CH:29]=[CH:30][C:31]=1[CH3:32])[C:6]([C:8]1[C:17](=[O:18])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]([CH2:19][C:20]2[N:25]=[C:24]([C:26]([NH2:37])=[O:27])[CH:23]=[CH:22][CH:21]=2)[CH:9]=1)=[O:7]

Komponenten

5

Edukt 2

HCID 27340594-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chlorideHCID 668794056-[3-(3,4-dimethyl-benzoyl)-4-oxo-4H-quinolin-1-ylmethyl]-pyridine-2-carboxylic acid hydrochloride

Produkt 1

HCID 577546416-[3-(3,4-Dimethyl-benzoyl)-4-oxo-4H-quinolin-1-ylmethyl]-pyridine-2-carboxylic acid amideAusbeute 68,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 222AmmoniaLösungsmittelHCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

27 mg (0.06 mmol) of 6-[3-(3,4-dimethyl-benzoyl)-4-oxo-4H-quinolin-1-ylmethyl]-pyridine-2-carboxylic acid hydrochloride was dissolved in a mixture of 2 mL DMSO and 0.2 mL 2 M methanolic ammonia followed by the addition of 100 mg (0.36 mmol) of 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride. The mixture was stirred for 1 h at r.t. followed by purification on reverse-phase HPLC and flash chromatography to give 17 mg of a white solid. LC-MSD, m/z for C25H21N3O3 [M+H]+=412.2; HPLC retention time: 1.7 min.

Aufarbeitung

  1. customfollowed by purification on reverse-phase HPLC and flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-750ed0afc44d4cd290cfc3a6c2ad67b4
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07557213B2

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