Triethylamine → N-[4-[2-Ethyl-4-(3-methylphenyl)-1,3-thiazol-5-YL]-2-pyridyl]cyclohexanecarboxamide

HRID 1727358Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1727358
[CH2:1]([C:3]1[S:4][C:5]([C:15]2[CH:20]=[CH:19][N:18]=[C:17]([NH2:21])[CH:16]=2)=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH3:14])[CH:9]=2)[N:7]=1)[CH3:2].[CH:22]1([C:28](Cl)=[O:29])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1.C(N(CC)CC)C.C(=O)([O-])O.[Na+]>O1CCCC1>[CH2:1]([C:3]1[S:4][C:5]([C:15]2[CH:20]=[CH:19][N:18]=[C:17]([NH:21][C:28]([CH:22]3[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]3)=[O:29])[CH:16]=2)=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH3:14])[CH:9]=2)[N:7]=1)[CH3:2]

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 75938Cyclohexanecarbonyl chlorideHCID 516892Sodium BicarbonateHCID 98573494-[2-ethyl-4-(3-methylphenyl)-1,3-thiazol-5-yl]pyridin-2-amine

Produkt 1

HCID 10158193N-[4-[2-Ethyl-4-(3-methylphenyl)-1,3-thiazol-5-YL]-2-pyridyl]cyclohexanecarboxamideAusbeute 75,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 4-[2-ethyl-4-(3-methylphenyl)-1,3-thiazol-5-yl]-2-pyridylamine (0.80 g, 2.7 mmol) in tetrahydrofuran (10 mL) were added cyclohexanecarbonyl chloride (0.40 mL, 3.0 mmol) and triethylamine (0.39 mL, 2.8 mmol) sequentially, and the mixture was stirred for 1 hour at room temperature. To the reaction mixture was added an aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate. The extracts were washed with an aqueous sodium hydrogen carbonate solution, then, dried and concentrated. The residue was purified by silica gel column chromatography (hexane-ethyl acetate=20:1 to 4:1) to obtain a crystal. This crystal was washed with hexane to obtain a title compound (0.83 g, yield 75%).

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe extracts were washed with an aqueous sodium hydrogen carbonate solution
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate=20:1 to 4:1)
  6. customto obtain a crystal
  7. washThis crystal was washed with hexane

Quellen und Nachweise

ORD-Eintrag
ord-d3c5188e782540dda8b0b1f7653c3a5c
Quelldatensatz
uspto-grants-2009_02
Patentnummer
US07495018B2

Notizen zur Reaktion

Wird geladen…