Triethylamine → 2-(4-Morpholinylcarbonyl)-1,3-thiazol-5-amine

HRID 1070624

Reaktionsgleichung

Reaktionsgleichung von HRID 1070624
[N:1]1([C:7](=[O:12])[C:8]([S:10][CH3:11])=S)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.S(=O)(=O)(O)O.[NH2:18][CH2:19]C#N.C([N:24](CC)CC)C>CO>[N:1]1([C:7]([C:8]2[S:10][C:11]([NH2:24])=[CH:19][N:18]=2)=[O:12])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 196971Aminoacetonitrile sulfate (1:1)HCID 22397235Methyl 4-morpholinyl(oxo)ethanedithioate

Produkt 1

HCID 223972262-(4-Morpholinylcarbonyl)-1,3-thiazol-5-amineAusbeute 31 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Versuchsvorschrift

To a stirring mixture of methyl 4-morpholinyl(oxo)ethanedithioate (Preparation 25, 500 mg) and aminoacetonitrile bisulfate (564 mg) in MeOH (10 mL) at 0° C. is added triethylamine in MeOH (5 mL). The mixture is stirred overnight and allowed to warm to ambient temperature. The solution is filtered, and solvent removed from the filtrate. The residue is washed with water (15 mL) and extracted with EtOAc (3×20 mL), dried over MgSO4, and the solvent removed. The residue is purified by SiO2 flash column chromatography (eluent 3/1 EtOAc/hexane) to afford 161 mg (31%) of the title compound as a light brown solid. Physical characteristics: 1H NMR (CDCl3) δ3.78, 4.35, 7.05; IR (diffuse reflectance) 3321, 3217, 2858, 1580, 1438, 1418, 1348, 1276, 1178, 1113, 1003, 834, 783, 731, 619 cm−1; MS (ESI+) m/z 214 (M+H)+. Anal. Found: C, 45.24; H, 5.33; N, 19.42.

Aufarbeitung

  1. filtrationThe solution is filtered
  2. customsolvent removed from the filtrate
  3. washThe residue is washed with water (15 mL)
  4. extractionextracted with EtOAc (3×20 mL)
  5. dry with materialdried over MgSO4
  6. customthe solvent removed
  7. customThe residue is purified by SiO2 flash column chromatography (eluent 3/1 EtOAc/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-8b5410d9198848f39eb671481d19ace6
Quelldatensatz
uspto-grants-2005_06
Patentnummer
US06903097B2

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