Water → 2-(6-methanesulfonyl-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid tert-butylamide

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Reaction Steps

In a round-bottomed flask, 2-(6-methanesulfonyl-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid tert-butylamide (76 mg, 0.137 mmol) was dissolved in dichloromethane (0.7 ml) and trifluoroacetic acid (0.42 ml, 5.45 mmol) was added. The reaction mixture was stirred at room temperature for 2.5 h then concentrated. The residue was dissolved in dichloromethane (0.7 ml) and ethylenediamine (0.55 ml, 8.14 mmol) was added. The reaction was stirred at room temperature for 1 h then water and ethyl acetate were added. The resulting suspension was filtered and washed with hot water and ethyl acetate. The product collected was dried under high vacuum to provide 39 mg (67%) of 2-(6-methanesulfonyl-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid tert-butylamide as a light yellow powder. MS: (2M+Na)+=875; 1H NMR (DMSO-d6, 300 MHz): δ (ppm) 12.89 (br. s, 1H), 9.13 (s, 1H), 8.71 (d, J=8.3 Hz, 1H), 8.46 (s, 1H), 8.42 (s, 1H), 7.92 (s, 1H), 7.76 (d, J=8.7 Hz, 1H), 4.31 (s, 3H), 3.35 (s, 3H), 1.55 (s, 9H).

Provenance & Evidence