Triethylamine → HCID 67002189, compound

Participants

Reaction Conditions

Reaction Steps

In a 15 mL round-bottomed flask, 2-cyclopropyl-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid piperidin-3-ylamide hydrochloride (200 mg, 0.44 mmol) was dissolved in CH2Cl2 (3 mL) and cooled to 0° C. Added triethylamine (0.12 mL, 0.88 mmol) followed by methanesulfonyl chloride (0.04 mL, 0.48 mmol). The reaction mixture was stirred at room temperature for 6 h then diluted with 30 mL of CH2Cl2 and washed with water (5 mL). The aqueous layer was extracted with CH2Cl2 (30 mL) and the combined organic layers were dried over Na2SO4, filtered and concentrated. The residue was purified by chromatography over 12 g SiO2 with EtOAc/Hexanes (gradient: 0-100% EtOAc) to provide 174 mg (89%) of 2-cyclopropyl-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (1-methanesulfonyl-piperidin-3-yl)-amide as a white foam.

Provenance & Evidence