Ethylenediamine → HCID 71288253, compound

Participants

Reaction Steps

To a solution of 2-(6-chloro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanylethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid [1-(1-methanesulfonyl-azetidin-3-yl)-ethyl]-amide (30 mg, 0.049 mmol) in CH2Cl2 (2 mL) was added TFA (0.3 mL, 3.89 mmol). The yellow reaction mixture was stirred at room temperature for 3 h then concentrated. The residue was redissolved in CH2Cl2 (2 mL) and ethylenediamine (0.3 mL, 4.49 mmol) was added. The reaction mixture was stirred at room temperature for 1 h then quenched with water and extracted with MeOH/CH2Cl2 (1:9). The organic layer was washed with water and the aqueous was back-extracted with CH2Cl2. The combined organics were concentrated and the residue was triturated with MeOH/EtOAc/Et2O to afford 15 mg (63%) of 2-(6-chloro-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid [1-(1-methanesulfonyl-azetidin-3-yl)-ethyl]-amide as a pale yellow solid. MS (M+H)+=488; 1H NMR (DMSO-d6, 300 MHz): δ (ppm) 9.05 (br. s., 1H), 8.86 (s, 1H), 8.63 (s, 1H), 8.41 (d, J=8.7 Hz, 1H), 7.92 (s, 1H), 7.26 (d, J=8.7 Hz, 1H), 4.35-4.45 (m, 1H), 4.22-4.33 (m, 1H), 4.12 (s, 3H), 4.04-4.10 (m, 1H), 3.62-3.74 (m, 1H), 3.45-3.58 (m, 1H), 3.25 (s, 3H), 2.57-2.68 (m, 1H), 1.38 (d, J=6.8 Hz, 3H).

Provenance & Evidence