Methanol → (R)-cyclopropyl-{[2-(7-methoxy-thieno[3,2-b]pyridin-2-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carbonyl]-amino}-acetic acid

Participants

Reaction Conditions

Reaction Steps

To a solution of sodium methoxide in MeOH (0.5 M, 0.97 mL, 0.49 mmol) was added 2-(7-chloro-thieno[3,2-b]pyridin-2-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid [(R)-2-(3-cyano-azetidin-1-yl)-1-cyclopropyl-2-oxo-ethyl]-amide (35 mg, 0.056 mmol) and reaction mixture was stirred at 100° C. for 1 h under microwave assisted conditions. The reaction mixture was evaporated to dryness and the crude residue was purified by preparative TLC (CH2Cl2:MeOH:NH4OH, 80:19:1) to give 18 mg (57%) of (R)-cyclopropyl-{[2-(7-methoxy-thieno[3,2-b]pyridin-2-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carbonyl]-amino}-acetic acid. MS: (M+H)+=554; (M−H])−=552.

Provenance & Evidence