Ethylenediamine → HCID 178481760, compound

Participants

Reaction Steps

In a 25 mL round-bottomed flask, 2-(6-chloro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (trans-4-hydroxycyclohexyl)amide (60 mg, 0.108 mmol) was dissolved in dichloromethane (3 mL). Trifluoroacetic acid (0.2 mL, 2.6 mmol) was added and the orange reaction mixture was stirred at room temperature for 15 h. Additional trifluoroacetic acid (0.7 mL) was added and the reaction stirred for an additional 5 h. The reaction mixture was then concentrated under reduced pressure. The resultant crude solid was dissolved in dichloromethane (3 mL) and ethylenediamine (0.20 mL, 2.96 mmol) was added. The light yellow reaction mixture was stirred at room temperature for 20 h. The reaction mixture was concentrated and the residue was precipitated with water. The suspension was stirred for 1 h and the crude solid collected by filtration. The crude solid was sequentially washed with water, dichloromethane, ethyl acetate, and hexanes to afford 28 mg (60%) of 2-(6-chloro-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (trans-4-hydroxy-cyclohexyl)amide as a light yellow solid. MS: [M+H]+=525; 1H NMR (300 MHz, DMSO-d6) δ: 9.08 (s, 2H), 8.40 (s, 1H), 8.43 (d, J=1.0 Hz, 1H), 8.02 (d, J=1.0 Hz, 1H), 8.01 (s, 1H), 7.28 (dd, J=8.6, 2.0 Hz, 1H), 4.45-4.76 (m, 1H), 4.17 (s, 3H), 3.70-3.96 (m, 1H), 3.43-3.59 (m, 1H), 2.07 (d, J=11.1 Hz, 2H), 1.92 (d, J=10.6 Hz, 2H), 1.18-1.55 (m, 4H).

Provenance & Evidence