Sodium Bicarbonate → N-[4-[4-(3-methylphenyl)-2-(1-methylpiperidin-4-yl)-1,3-thiazol-5-yl]-2-pyridyl]benzamide

HRID 1268740Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1268740
Br.Br[CH:3]([C:13]1[CH:18]=[CH:17][N:16]=[C:15]([NH:19][C:20](=[O:27])[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:14]=1)[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH3:12])[CH:7]=1)=O.[CH3:28][N:29]1[CH2:34][CH2:33][CH:32]([C:35](=[S:37])[NH2:36])[CH2:31][CH2:30]1.C(=O)([O-])O.[Na+]>CN(C)C=O>[CH3:12][C:8]1[CH:7]=[C:6]([C:4]2[N:36]=[C:35]([CH:32]3[CH2:33][CH2:34][N:29]([CH3:28])[CH2:30][CH2:31]3)[S:37][C:3]=2[C:13]2[CH:18]=[CH:17][N:16]=[C:15]([NH:19][C:20](=[O:27])[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH:14]=2)[CH:11]=[CH:10][CH:9]=1

Komponenten

5

Edukt 3

HCID 516892Sodium BicarbonateHCID 155845011-Methylpiperidine-4-CarbothioamideHCID 18446669N-[4-[1-bromo-2-(3-methylphenyl)-2-oxoethyl]-2-pyridyl]benzamide hydrobromide

Produkt 1

HCID 18446686N-[4-[4-(3-methylphenyl)-2-(1-methylpiperidin-4-yl)-1,3-thiazol-5-yl]-2-pyridyl]benzamideAusbeute 47 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of N-[4-[1-bromo-2-(3-methylphenyl)-2-oxoethyl]-2-pyridyl]benzamide hydrobromide (0.60 g, 1.2 mmol) and 1-methylpiperidine-4-carbothioamide (0.19 g, 1.18 mmol) in N,N-dimethylformamide (20 mL) was stirred at room temperature for 14 hrs. Into the reaction mixture was poured aqueous sodium hydrogen carbonate solution and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogen carbonate solution, dried and concentrated. The residue was purified by column chromatography (packing: Chromatorex NH DM1020 (product name, manufactured by Fuji Silysia Chemical Ltd.), hexane-ethyl acetate=2:1) and the resulting crystals were recrystallized from ethyl acetate to give the title compound (0.26 g, yield 46%).

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated aqueous sodium hydrogen carbonate solution
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography (packing: Chromatorex NH DM1020 (product name, manufactured by Fuji Silysia Chemical Ltd.), hexane-ethyl acetate=2:1)
  6. customthe resulting crystals were recrystallized from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-be21d7ab60f44e23bcda25f6aa1166ba
Quelldatensatz
uspto-grants-2007_04
Patentnummer
US07199124B2

Notizen zur Reaktion

Wird geladen…