3-Pyridinecarbonyl chloride, hydrochloride (1:1) → N-[4-(4-Methoxyphenyl)-5-{2-[(pyridine-3-carbonyl)amino]pyridin-4-yl}-1,3-thiazol-2-yl]pyridine-3-carboxamide

HRID 1178589

Reaktionsgleichung

Cl.[C:2](Cl)(=[O:9])[C:3]1[CH:8]=[CH:7][CH:6]=[N:5][CH:4]=1.[NH2:11][C:12]1[S:13][C:14]([C:25]2[CH:30]=[CH:29][N:28]=[C:27]([NH2:31])[CH:26]=2)=[C:15]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)[N:16]=1.[C:32](=[O:35])([O-])O.[Na+]>CN(C)C1C=CN=CC=1.CN(C)C(=O)C>[CH3:24][O:23][C:20]1[CH:21]=[CH:22][C:17]([C:15]2[N:16]=[C:12]([NH:11][C:32](=[O:35])[C:3]3[CH:8]=[CH:7][CH:6]=[N:5][CH:4]=3)[S:13][C:14]=2[C:25]2[CH:30]=[CH:29][N:28]=[C:27]([NH:31][C:2]([C:3]3[CH:4]=[N:5][CH:6]=[CH:7][CH:8]=3)=[O:9])[CH:26]=2)=[CH:18][CH:19]=1

Komponenten

Reaktionsbedingungen

Temperatur: 70 °C

Versuchsvorschrift

Nicotinoyl chloride hydrochloride (0.72 g, 4.1 mmol) and 4-dimethylaminopyridine (0.05 g, 0.4 mmol) were added to a solution of 4-[2-amino-4-(4-methoxyphenyl)-1,3-thiazol-5-yl]-2-pyridylamine (0.41 g, 1.4 mmol) in N,N-dimethylacetamide (10 mL) and the mixture was stirred at 70° C. for 19 hours. After the reaction mixture was cooled to room temperature, a saturated aqueous solution of sodium hydrogencarbonate (50 mL) was added. The resulting crude crystals were collected by filtration and washed with water. The crude crystals were recrystallized from ethanol to obtain 0.23 g (0.44 mmol, yield 33%) of the title compound.

Aufarbeitung

temperatureAfter the reaction mixture was cooled to room temperature
filtrationThe resulting crude crystals were collected by filtration
washwashed with water
customThe crude crystals were recrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag: ord-e0e65aea05dd4ee1af7e29885f377c79
Quelldatensatz: uspto-grants-2007_10
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07276527B2

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