Reaktion #1269155

Reaktionsgleichung

8-(4-methyl-1-piperazinyl)-4-oxo-4H-chromene-2-carboxylic acid hydrochloride

4-(4-morpholinyl)Aniline

4-Amino-3-hydroxyphenylmorpholine

1-hydroxybenzotriazole

triethylamine

→

crude product

8-(4-methyl-1-piperazinyl)-N-[4-(4-morpholinyl)phenyl]-4-oxo-4H-chromene-2-carboxamide

Lösungsmittel

N,N-dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeto give a clear solution
2. 2
   workup.ADDITIONThe following were added in order
3. 3
   workup.STIRRINGThe reaction stirred overnight at room temperature
4. 4
   EinengenThe solution was concentrated in vacuo
5. 5
   Sonstigethe remains were partitioned between chloroform/saturated sodium bicarbonate
6. 6
   Extraktionextracted (×3) with chloroform
7. 7
   Trocknendried (MgSO4)
8. 8
   Einengenconcentrated in vacuo

Vorschrift

8-(4-methyl-1-piperazinyl)-4-oxo-4H-chromene-2-carboxylic acid hydrochloride (Reference Example 1) (400 mg, 1.23 mmol) was suspended in anhydrous N,N-dimethylformamide (20 ml) and triethylamine (0.69 ml, 4.92 mmol) was added to give a clear solution. The following were added in order: 1-hydroxybenzotriazole (HOBt (205 mg, mol)), O-(1H-Benzotriazol-1-yl)-N,N,N′,N′-pentamethylene-uronium tetrafluoroborate (TBTU (435 mg, 3.1 mmol)) then 4-(dimethylamino)pyridine (25 mg). After stirring for 5 min at room temperature, 4-(4-morpholinyl)Aniline (Reference Example 21) (220 mg, mmol). The reaction stirred overnight at room temperature. The solution was concentrated in vacuo, the remains were partitioned between chloroform/saturated sodium bicarbonate, extracted (×3) with chloroform, dried (MgSO4) and concentrated in vacuo to give the crude product.

Quelle