8-Hydroxyquinoline → 2-(4-Amino-2-oxopyridin-1(2H)-yl)-N-benzyl-4-methylthiazole-5-carboxamide

HRID 1887282

Reaktionsgleichung

Reaktionsgleichung von HRID 1887282
[CH2:1]([NH:8][C:9]([C:11]1[S:15][C:14](Br)=[N:13][C:12]=1[CH3:17])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:18][C:19]1[CH:24]=[CH:23][NH:22][C:21](=[O:25])[CH:20]=1.C(=O)([O-])[O-].[K+].[K+].OC1C=CC=C2C=1N=CC=C2>CS(C)=O.[Cu]I.O>[NH2:18][C:19]1[CH:24]=[CH:23][N:22]([C:14]2[S:15][C:11]([C:9]([NH:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[O:10])=[C:12]([CH3:17])[N:13]=2)[C:21](=[O:25])[CH:20]=1

Komponenten

8

Edukt 4

HCID 19238-HydroxyquinolineHCID 11430Potassium CarbonateHCID 5735304-Amino-1,2-dihydropyridin-2-oneHCID 579593962-Bromo-4-methyl-thiazole-5-carboxylic acid benzylamide

Produkt 1

HCID 249852702-(4-Amino-2-oxopyridin-1(2H)-yl)-N-benzyl-4-methylthiazole-5-carboxamideAusbeute 49,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To a degassed solution of N-benzyl-2-bromo-4-methylthiazole-5-carboxamide (1.58 g, 5.00 mmol), 4-aminopyridin-2(1H)-one (0.72 g, 6.50 mmol), potassium carbonate (2.00 g, 14.40 mmol) and 8-hydroxyquinoline (0.08 g, 0.50 mmol) in dimethyl sulfoxide (30 mL) was added copper(I) iodide (0.10 g, 0.50 mmol). The reaction mixture was heated at 75-80 C. for 16 hours, then cooled to ambient temperature. Water (300 mL) was added to the mixture and the crude product was precipitated and collected by filtration. The crude product was subjected to column chromatography to afford the title compound as a white solid (0.84 g, 49%): mp 171-172° C.; 1H NMR (300 MHz, DMSO-d6) δ 8.68 (t, J=5.7 Hz, 1H), 8.40 (d, J=7.8 Hz, 1H), 7.32-7.19 (m, 5H), 6.80 (s, 2H), 6.07 (dd, J=7.8, 1.8, Hz, 1H), 5.38 (d, J=1.8 Hz, 1H), 4.37 (d, J=5.7 Hz, 2H), 2.50 (s, 3H); 13C NMR (75 MHz, DMSO-d6) δ 162.2, 160.8, 157.7, 154.6, 150.0, 140.0, 131.5, 128.7, 127.7, 127.1, 122.9, 103.4, 90.5, 43.0, 17.5; MS (ES+) m/z 341.2 (M+1).

Aufarbeitung

  1. temperatureThe reaction mixture was heated at 75-80 C
  2. customthe crude product was precipitated
  3. filtrationcollected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-af9b9e96cf5346359289a645c60eeb0d
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08501746B2

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