Benzylamine → [5-(2-Benzylamino-4-pyridyl)-4-(3-methylphenyl)-1,3-thiazol-2-yl]amine

HRID 1268733Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1268733
F[C:2]1[CH:7]=[C:6]([C:8]2[S:12][C:11]([NH2:13])=[N:10][C:9]=2[C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[CH:15]=2)[CH:5]=[CH:4][N:3]=1.[CH2:21]([NH2:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(=O)([O-])O.[Na+]>>[CH2:21]([NH:28][C:2]1[CH:7]=[C:6]([C:8]2[S:12][C:11]([NH2:13])=[N:10][C:9]=2[C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[CH:15]=2)[CH:5]=[CH:4][N:3]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Komponenten

4

Edukt 3

HCID 7504BenzylamineHCID 516892Sodium BicarbonateHCID 9878963[5-(2-Fluoro-4-pyridyl)-4-(3-methylphenyl)-1,3-thiazol-2-yl]amine

Produkt 1

HCID 21964259[5-(2-Benzylamino-4-pyridyl)-4-(3-methylphenyl)-1,3-thiazol-2-yl]amineAusbeute 43 %

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

A mixture of [5-(2-fluoro-4-pyridyl)-4-(3-methylphenyl)-1,3-thiazol-2-yl]amine (0.29 g, 1.0 mmol) and benzylamine (1.2 mL, 11 mmol) was stirred at 150° C. for 3 hrs. The reaction mixture was cooled to room temperature, saturated aqueous sodium hydrogen carbonate solution was added and the mixture was extracted with ethyl acetate. The extract was washed with water, dried and concentrated. The residue was purified by silica gel column chromatography (hexane-ethyl acetate=1:1) to give the title compound (0.16 g, yield 41%).

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with water
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate=1:1)

Quellen und Nachweise

ORD-Eintrag
ord-e37c831fa5f741a3b982f8f5bf93c17d
Quelldatensatz
uspto-grants-2007_04
Patentnummer
US07199124B2

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