Sodium Bicarbonate → tert-Butyl 4-[5-(2-aminopyridin-4-yl)-4-(3-chlorophenyl)-1,3-thiazol-2-yl]piperidine-1-carboxylate

HRID 1727374Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1727374
Br.[NH2:2][C:3]1[CH:8]=[C:7]([CH:9](Br)[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[CH:13]=2)=O)[CH:6]=[CH:5][N:4]=1.[C:20]([O:24][C:25]([N:27]1[CH2:32][CH2:31][CH:30]([C:33](=[S:35])[NH2:34])[CH2:29][CH2:28]1)=[O:26])([CH3:23])([CH3:22])[CH3:21].C(=O)([O-])O.[Na+]>CN(C)C=O>[C:20]([O:24][C:25]([N:27]1[CH2:32][CH2:31][CH:30]([C:33]2[S:35][C:9]([C:7]3[CH:6]=[CH:5][N:4]=[C:3]([NH2:2])[CH:8]=3)=[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[CH:13]=3)[N:34]=2)[CH2:29][CH2:28]1)=[O:26])([CH3:23])([CH3:21])[CH3:22]

Komponenten

5

Edukt 3

HCID 516892Sodium BicarbonateHCID 2735648tert-Butyl 4-carbamothioylpiperidine-1-carboxylateHCID 17863029HCID 17863029, Verbindung

Produkt 1

HCID 57349380tert-Butyl 4-[5-(2-aminopyridin-4-yl)-4-(3-chlorophenyl)-1,3-thiazol-2-yl]piperidine-1-carboxylateAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 2-(2-amino-4-pyridyl)-2-bromo-1-(3-chlorophenyl)ethanone hydrobromide (2.74 g, 8.36 mmol) and 1-tert-butoxycarbonylpiperidine-4-carbothioamide in N,N-dimethylformamide (50 mL) was stirred at room temperature for 3 hours. Aqueous sodium hydrogen carbonate was added to the reaction mixture and extracted with ethyl acetate. The extracts were washed with water, dried, and concentrated. The residue was purified by silica gel column chromatography (ethyl acetate) and then purified by column chromatography (filler: Chromatorex NH DM1020 (trade name, manufactured by Fuji Silysia Chemical Ltd.), ethyl acetate). The obtained crude crystalline was recrystallized from ethyl acetate-hexane to give a title compound (1.94 g, yield 50%).

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe extracts were washed with water
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate)
  6. custompurified by column chromatography (filler: Chromatorex NH DM1020 (trade name, manufactured by Fuji Silysia Chemical Ltd.), ethyl acetate)
  7. customThe obtained crude
  8. customcrystalline was recrystallized from ethyl acetate-hexane

Quellen und Nachweise

ORD-Eintrag
ord-d9fec888457b4673b1b8c5856af86fce
Quelldatensatz
uspto-grants-2009_02
Patentnummer
US07495018B2

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