Triethylamine → N-[4-(3-Furyl)-5-(tetrahydropyran-4-ylcarbonyl)thiazol-2-yl]-2-methylpyridine-4-carboxamide

HRID 337519

Reaktionsgleichung

Reaktionsgleichung von HRID 337519
[O:1]1[CH2:6][CH2:5][CH:4]([C:7]([C:9]2[S:13][C:12]([NH2:14])=[N:11][C:10]=2[C:15]2[CH:19]=[CH:18][O:17][CH:16]=2)=[O:8])[CH2:3][CH2:2]1.Cl.[CH3:21][C:22]1[CH:23]=[C:24]([CH:28]=[CH:29][N:30]=1)[C:25](O)=[O:26].CCN=C=NCCCN(C)C.Cl.O.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C.C(=O)([O-])O.[Na+]>CN(C=O)C>[O:17]1[CH:18]=[CH:19][C:15]([C:10]2[N:11]=[C:12]([NH:14][C:25]([C:24]3[CH:28]=[CH:29][N:30]=[C:22]([CH3:21])[CH:23]=3)=[O:26])[S:13][C:9]=2[C:7]([CH:4]2[CH2:5][CH2:6][O:1][CH2:2][CH2:3]2)=[O:8])=[CH:16]1

Komponenten

8

Edukt 6

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27628242-methylpyridine-4-carboxylic Acid HydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 866124732-Amino-4-(3-furyl)thiazol-5-yl tetrahydropyran-4-yl ketone

Produkt 1

HCID 23144391N-[4-(3-Furyl)-5-(tetrahydropyran-4-ylcarbonyl)thiazol-2-yl]-2-methylpyridine-4-carboxamideAusbeute 51,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Compound 610 (100 mg, 0.359 mmol) was dissolved in DMF (3 mL), and 2-methylisonicotinic acid hydrochloride (249 mg, 1.44 mmol), EDC hydrochloride (558 mg, 2.91 mmol), 1-hydroxybenzotriazole monohydrate (463 mg, 3.02 mmol) and triethylamine (0.400 mL, 2.87 mmol) were added thereto, followed by stirring overnight at 80° C. The reaction mixture was poured into aqueous sodium hydrogencarbonate solution, followed by extraction with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate, and then the solvent was distilled away under reduced pressure. The resulting residue was purified through silica gel column chromatography (hexane:ethyl acetate=3:1), followed by recrystallizing from a mixed solvent of ethanol and water to afford the entitled Compound 615 (73.1 mg, 51%) as a white solid.

Aufarbeitung

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled away under reduced pressure
  5. customThe resulting residue was purified through silica gel column chromatography (hexane:ethyl acetate=3:1)
  6. customby recrystallizing from a mixed solvent of ethanol and water

Quellen und Nachweise

ORD-Eintrag
ord-f1d30238ebbd4c8198b18ef9feac02d3
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08889718B2

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