Diisopropylethylamine → (3-{[2-(6-chloro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carbonyl]-amino}-cyclopentyl)-carbamic acid tert-butyl ester

Participants

Reaction Steps

A round-bottomed flask was charged with 2-(6-chloro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (300 mg, 0.66 mmol) and (3-aminocyclopentyl)-carbamic acid tert-butylester hydrochloride (233 mg, 0.98 mmol). DMF (3 ml) was added followed by HATU (274 mg, 0.72 mmol) and N,N-diisopropylethylamine (0.30 ml, 1.72 mmol). The reaction mixture was stirred at room temperature for 30 min. Additional DMF (2 ml) was added and the light yellow suspension was stirred at room temperature overnight. Water was added and the resulting suspension was filtered, washed with water and petroleum ether and dried under high vacuum to afford 413 mg (99%) of (3-{[2-(6-chloro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carbonyl]-amino}-cyclopentyl)-carbamic acid tert-butyl ester as an off-white powder. The isolated product was determined to be a single diastereomer of unknown relative stereochemistry by NMR analysis.

Provenance & Evidence