Hydrochloric Acid → HCID 86677934, compound

Participants

Reaction Steps

To a solution of 2-(6-fluoro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanylethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid ((R)-1-pyridin-2-yl-ethyl)-amide (117 mg, 0.21 mmol) in CH2Cl2 (2 mL) was added TFA (1 mL, 13.0 mmol). The bright yellow-orange reaction mixture was stirred at room temperature for 3 h then concentrated. The residue was redissolved in CH2Cl2 (2 mL) and ethylene diamine (0.5 mL, 7.50 mmol) was added. The reaction mixture was stirred for 1 h then chromatographed directly with 50% to 100% EtOAc/hexanes to 5% MeOH/EtOAc. The white solid thus isolated was triturated with EtOAc then suspended in CH2Cl2 and MeOH (1:1, 6 mL). 1.0M HCl in MeOH (2 eq) was added which caused complete dissolution. The solution was concentrated and dried under high vacuum to afford 67 mg (69%) of 2-(6-fluoro-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid ((R)-1-pyridin-2-yl-ethyl)-amide hydrochloride as a light yellow solid. MS (M+H)+=416; 1H NMR (DMSO-d6, 300 MHz): δ (ppm) 12.93 (d, J=2.6 Hz, 1H), 9.13 (s, 1H), 8.83 (d, J=7.6 Hz, 1H), 8.73 (dd, J=8.9, 5.5 Hz, 1H), 8.59 (d, J=4.9 Hz, 1H), 8.44 (d, J=3.0 Hz, 1H), 8.07 (br. s., 1H), 7.76 (d, J=7.9 Hz, 1H), 7.68 (dd, J=9.6, 2.1 Hz, 1H), 7.53 (br. s., 1H), 7.05 (td, J=9.1, 1.9 Hz, 1H), 5.44 (quin, J=7.0 Hz, 1H), 4.15 (s, 3H), 1.67 (d, J=6.8 Hz, 3H).

Provenance & Evidence