Ethylenediamine → 2-cyclopropyl-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid [(R)-2,2-dimethyl-1-(pyrrolidine-1-carbonyl)-propyl]-amide

関与物質

反応手順

In a 10 mL round-bottomed flask, (R)-2-cyclopropyl-N-(3,3-dimethyl-1-oxo-1-(pyrrolidin-1-yl)butan-2-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (0.19 g, 0.34 mmol) was dissolved in dichloromethane (1.4 mL). Trifluoroacetic acid (1.05 mL, 13.7 mmol) was added and the light yellow reaction mixture was stirred at room temperature for 2 h then concentrated under reduced pressure. The residue was dissolved in toluene (3 mL), concentrated and then placed under high vacuum for 30 min. The resultant foam was dissolved in dichloromethane (1.4 mL) and ethylenediamine (1.40 mL, 20.7 mmol) was added. The light yellow reaction mixture was stirred at room temperature for 2 h then quenched with water and extracted with EtOAc (2×50 mL). The combined organic layers were washed with water and brine then dried over sodium sulfate, filtered and concentrated. The residue was purified by chromatography over 8 g SiO2 with MeOH/CH2Cl2 (gradient: 0-10% MeOH) to afford a yellow solid. Trituration with EtOAc provided 63 mg (50%) of 2-cyclopropyl-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid [(R)-2,2-dimethyl-1-(pyrrolidine-1-carbonyl)-propyl]-amide as a white powder. MS: (M+H)+=370; mp=201.0-203.0.

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