Water → 2-(5-cyano-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-(5-cyano-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanylethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid tert-butylamide (80 mg, 0.16 mmol) was dissolved in dichloromethane (0.8 ml) and trifluoroacetic acid (0.5 ml, 6.4 mmol) was added. The reaction mixture was stirred at room temperature for 2 h then concentrated. The residue was suspended in dichloromethane (0.8 ml) and ethylenediamine (0.65 ml, 9.63 mmol) was added. The light yellow suspension was stirred at room temperature for 1 h then water and ethyl acetate were added. The suspension was filtered and washed with hot water and ethyl acetate. The product collected was dried under high vacuum to provide 43 mg (73%) of 2-(5-cyano-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid tert-butylamide as a yellow powder. MS: (M+Na)+=396; 1H NMR (DMSO-d6, 300 MHz): δ (ppm) 12.48 (br. s., 1H), 9.10 (s, 1H), 8.87 (s, 1H), 8.41 (s, 1H), 7.93-8.05 (m, 1H), 7.78-7.90 (m, 2H), 4.23 (s, 3H), 1.54 (s, 9H).

Provenance & Evidence