Ethylenediamine → (6-Chloro-3-{7-[(R)-2-(3-cyano-azetidin-1-yl)-1-methyl-2-oxo-ethylcarbamoyl]-5H-pyrrolo[2,3-b]pyrazin-2-yl}-indazol-1-yl)-acetic acid

Participants

Reaction Steps

In a 5 mL pear-shaped flask, {6-chloro-3-[7-[(R)-2-(3-cyano-azetidin-1-yl)-1-methyl-2-oxo-ethylcarbamoyl]-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-indazol-1-yl}-acetic acid tert-butyl ester (30 mg, 0.043 mmol) was combined with CH2Cl2 (1 ml) to give a light yellow solution. TFA (0.10 ml, 1.3 mmol) was added and the reaction was stirred at room temperature for 2 h. The crude reaction mixture was concentrated in vacuo and redissolved in CH2Cl2. Ethylenediamine (88 μl, 1.3 mmol) was added dropwise and the reaction was stirred at room temperature for 30 min. The crude reaction mixture was concentrated in vacuo. The residue was dissolved in water and it was lyophilized overnight. The yellow waxy solid was suspended in water and filtered, washing with water then dried on high vacuum to give 8 mg (32%) of (6-Chloro-3-{7-[(R)-2-(3-cyano-azetidin-1-yl)-1-methyl-2-oxo-ethylcarbamoyl]-5H-pyrrolo[2,3-b]pyrazin-2-yl}-indazol-1-yl)-acetic acid as a yellow solid. MS: (M+H)+=507.

Provenance & Evidence