Acetyl chloride → tert-Butyl 4-[5-(2-acetamidopyridin-4-yl)-4-(3-chlorophenyl)-1,3-thiazol-2-yl]piperidine-1-carboxylate

HRID 1727375Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1727375
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[S:15][C:16]([C:26]3[CH:31]=[CH:30][N:29]=[C:28]([NH2:32])[CH:27]=3)=[C:17]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=3)[N:18]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:33](Cl)(=[O:35])[CH3:34].C(N(CC)CC)C.C(=O)([O-])O.[Na+]>O1CCCC1>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([C:14]2[S:15][C:16]([C:26]3[CH:31]=[CH:30][N:29]=[C:28]([NH:32][C:33](=[O:35])[CH3:34])[CH:27]=3)=[C:17]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=3)[N:18]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

6

Edukt 4

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 57349380tert-Butyl 4-[5-(2-aminopyridin-4-yl)-4-(3-chlorophenyl)-1,3-thiazol-2-yl]piperidine-1-carboxylate

Produkt 1

HCID 57349381tert-Butyl 4-[5-(2-acetamidopyridin-4-yl)-4-(3-chlorophenyl)-1,3-thiazol-2-yl]piperidine-1-carboxylateAusbeute 102,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of [4-[2-(1-tert-butoxycarbonylpiperidin-4-yl)-4-(3-chlorophenyl)-1,3-thiazol-5-yl]-2-pyridylamine (1.60 g, 3.40 mmol) in tetrahydrofuran (20 mL) were added acetyl chloride (0.25 mL, 3.52 mmol) and triethylamine (0.50 mL, 3.58 mmol) at 0° C. sequentially, and the resulting mixture 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 brine, dried, and concentrated. The residue was purified by column chromatography (filler: Chromatorex NH DM1020 (trade name, manufactured by Fuji Silysia Chemical Ltd.), hexane-ethyl acetate=1:1) to give a title compound (1.79 g, yield 98%).

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe extracts were washed with brine
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography (filler: Chromatorex NH DM1020 (trade name, manufactured by Fuji Silysia Chemical Ltd.), hexane-ethyl acetate=1:1)

Quellen und Nachweise

ORD-Eintrag
ord-25502566e52048fabecc89ee6b5c66e0
Quelldatensatz
uspto-grants-2009_02
Patentnummer
US07495018B2

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