Water → HCID 178481761, compound

Participants

Reaction Steps

In a round-bottomed flask, (cis-3-{[2-(6-fluoro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carbonyl]-amino}-cyclobutyl)carbamic acid tert-butyl ester (144 mg, 0.236 mmol) was dissolved in dichloromethane (1.2 ml) and trifluoroacetic acid (0.73 ml, 9.48 mmol) was added. The reaction mixture was stirred at room temperature for 2 h then concentrated. The residue was suspended in dichloromethane (1.2 ml) and ethylenediamine (0.96 ml, 14.2 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 was dried under high vacuum to provide 86 mg (91%) of 2-(6-fluoro-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (cis-3-amino-cyclobutyl)-amide as a light yellow powder. MS: (M+H)+=380; 1H NMR (DMSO-d6, 300 MHz): δ (ppm) 9.09 (s, 1H), 8.54 (dd, J=8.7, 5.3 Hz, 1H), 8.41 (s, 1H), 8.28 (d, J=7.6 Hz, 1H), 7.71 (dd, J=9.8, 1.9 Hz, 1H), 7.28 (td, J=9.1, 1.9 Hz, 1H), 5.54 (br. s., 2H), 4.15 (s, 3H), 4.04-4.18 (m, 1H), 3.07-3.22 (m, 1H), 2.65-2.80 (m, 2H), 1.66-1.80 (m, 2H).

Provenance & Evidence