Borane → 2-(Morpholin-4-ylmethyl)-1,3-thiazol-5-amine

HRID 411209

Reaktionsgleichung

Reaktionsgleichung von HRID 411209
[N:1]1([C:7]([C:9]2[S:10][C:11]([NH2:14])=[CH:12][N:13]=2)=O)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.B>C1COCC1>[N:1]1([CH2:7][C:9]2[S:10][C:11]([NH2:14])=[CH:12][N:13]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Komponenten

4

Edukt 2

HCID 6331BoraneHCID 223972262-(4-Morpholinylcarbonyl)-1,3-thiazol-5-amine

Produkt 1

HCID 223971412-(Morpholin-4-ylmethyl)-1,3-thiazol-5-amineAusbeute 35,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

To a solution of 2-(4-morpholinylcarbonyl)-1,3-thiazol-5-amine (Preparation 26, 1.0 g) in THF (10 mL) under nitrogen at ambient temperature is added borane (1.0 M solution in THF, 9.39 mL). The bright yellow mixture is heated to reflux (85° C.) for 1 h. The mixture is cooled to ambient temperature, quenched with aq. NH4Cl, and extracted with EtOAc (3×75 mL). The organic layer is dried (MgSO4) and the solvent removed. The residue is purified by column chromatography (eluent 2% MeOH/CH2Cl2) to afford 329 mg (35%) of the title compound as a yellow oil. Physical characteristics: 1H NMR (CDCl3) δ 2.49, 3.61, 3.65, 6.84; MS (ESI+) m/z 200 (M+H)+.

Aufarbeitung

  1. temperatureThe bright yellow mixture is heated
  2. temperatureThe mixture is cooled to ambient temperature
  3. customquenched with aq. NH4Cl
  4. extractionextracted with EtOAc (3×75 mL)
  5. dry with materialThe organic layer is dried (MgSO4)
  6. customthe solvent removed
  7. customThe residue is purified by column chromatography (eluent 2% MeOH/CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-e59034d651c340d6b5cc477239038f4a
Quelldatensatz
uspto-grants-2003_05
Patentnummer
US06559145B2

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