Trifluoroacetic anhydride → HCID 71288927, compound

Participants

Reaction Conditions

Reaction Steps

In a 25 mL pear-shaped flask, 2-(6-chloro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (trans-3-carbamoyl-cyclohexyl)-amide (72 mg, 0.124 mmol) was combined with pyridine (412 μl) to give a off-white solution. The reaction mixture was cooled at 0° C. and trifluoroacetic anhydride (0.71 M in pyridine, 26 μl, 0.18 mmol) was added dropwise. The reaction mixture was allowed to stir at room temperature for 30 min and then concentrated. The residue was purified by chromatography over SiO2 with EtOAc/hexanes (gradient: 0-50% EtOAc) to afford 27 mg (39%) of 2-(6-chloro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (trans-3-cyano-cyclohexyl)-amide as a white solid. 1H NMR (300 MHz, DMSO-d6) δ: 9.14 (s, 1H), 8.66 (s, 1H), 8.40 (d, J=8.7 Hz, 1H), 8.06 (d, J=7.9 Hz, 1H), 8.01 (d, J=1.0 Hz, 1H), 7.38 (dd, J=8.7, 1.0 Hz, 1H), 5.73 (s, 2H), 4.18 (s, 3H), 4.09-4.28 (m, 1H), 3.59 (t, J=7.9 Hz, 2H), 3.41-3.60 (br. s., 1H), 2.24 (app. d, J=12.5 Hz, 1H), 2.07 (app. d, J=12.1 Hz, 1H), 1.59-1.91 (m, 5H), 1.39-1.59 (m, 1H), 0.86 (t, J=7.9 Hz, 2H), −0.08 (s, 9H).

Provenance & Evidence