Tert-Butylamine → HCID 90040556, compound

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Reaction Steps

To a solution of 2-bromo-3-chloro-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (600 mg, 1.48 mmol) in DMF (5 mL) was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (650 mg, 3.39 mmol) and HOBT (520 mg, 3.39 mmol) and the mixture stirred for 10 min. 2-methylpropan-2-amine (432 mg, 5.9 mmol) was added and the mixture stirred at room temperature for 16 h, then diluted with 10% citric acid and ethyl acetate. The organic layer was separated and washed with 10% citric acid, saturated aqueous NaHCO3 and brine, then concentrated in vacuo and purified by chromatography (silica, 5-20% ethyl acetate in hexanes) to give 2-bromo-N-tert-butyl-3-chloro-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (530 mg, 1.15 mmol, 78%) as a white solid. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm: 8.30 (s, 1H), 7.72 (s, 1H), 5.64 (s, 2H), 3.57 (t, J=8.3 Hz, 2H), 1.56 (s, 9H), 0.96 (t, J=8.3 Hz, 2H), 0.01 (s, 9H).

Provenance & Evidence