Ethylenediamine → HCID 178464934, 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 [1-(trans-3-cyano-cyclobutyl)-ethyl]-amide (44 mg, 0.08 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 (0.4 mL, 6.0 mmol) was added. The reaction mixture was stirred at room temperature for 1 h then quenched with water and extracted with 5% MeOH/CH2Cl2 (2×). The combined organics were concentrated and the residue was triturated with EtOAc to afford 19 mg (57%) of 2-(6-fluoro-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid [1-(trans-3-cyanocyclobutyl)-ethyl]-amide as a light yellow solid. MS: (M+H)+=418; 1H NMR (DMSO-d6, 300 MHz): δ (ppm) 9.08 (s, 1H), 8.43 (s, 1H), 8.40 (dd, J=8.9, 5.5 Hz, 1H), 7.96 (d, J=9.1 Hz, 1H), 7.70 (dd, J=9.8, 2.3 Hz, 1H), 7.29 (td, J=9.1, 1.9 Hz, 1H), 4.19-4.31 (m, 1H), 4.14 (s, 3H), 2.64-2.77 (m, 2H), 2.34-2.45 (m, 1H), 2.22-2.33 (m, 3H), 1.18 (d, J=6.4 Hz, 3H).

Provenance & Evidence