Reaktion #43275

Reaktionsgleichung

2-(5,5-dioxo-5,10-dihydrophenothiazin-2-yl)-3-(tetrahydropyran-4-yl)propionic acid

1-methyl-1H-pyrazole-3-amine

N,N-diisopropylethylamine

HATU

HOAT

→

2-(5,5-Dioxo-5,10-dihydrophenothiazin-2-yl)-N-(1-methyl-1H-pyrazol-3-yl)-3-(tetrahydropyran-4-yl)propionamide

Lösungsmittel

ethyl acetate

dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenwashed three times with in each case 50 ml of water and saturated sodium chloride solution
2. 2
   TrocknenThe organic phase is dried over MgSO4
3. 3
   Sonstigethe solvent is then removed under reduced pressure
4. 4
   SonstigeThe residue is purified by RP-HPLC

Vorschrift

600 mg of 2-(5,5-dioxo-5,10-dihydrophenothiazin-2-yl)-3-(tetrahydropyran-4-yl)propionic acid, 120 mg of commercially available 1-methyl-1H-pyrazole-3-amine and 729 μl of N,N-diisopropylethylamine are dissolved in 5 ml of dimethylformamide. 561 mg of HATU and 200 mg of HOAT are added, and the mixture is stirred at room temperature for two hours. The reaction mixture is then diluted by addition of 200 ml of ethyl acetate and washed three times with in each case 50 ml of water and saturated sodium chloride solution. The organic phase is dried over MgSO4, and the solvent is then removed under reduced pressure. The residue is purified by RP-HPLC. This gives 200 mg of 2-(5,5-dioxo-5,10-dihydrophenothiazin-2-yl)-N-(11-methyl-1H-pyrazol-3-yl)-3-(tetrahydropyran-4-yl)propionamide as a colorless lyophilisate.

Quelle