反应详情

A 25 mL round-bottom flask was charged with 2-(6-chloro-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (3-hydroxy-cyclohexyl) amide (22 mg, 0.052 mmol) and dichloromethane (5 mL). Dess-Martin periodinane (34.0 mg, 0.08 mmol) was added in one portion to the reaction mixture. The reaction mixture was placed under Ar and stirred for 2 h at room temperature. DMF (1.5 mL) was added and the reaction mixture was stirred for an additional 18 h. The reaction mixture was diluted to 100 mL with EtOAc and washed with sat NaHCO3 (3×20 mL). The crude white precipitate was filtered and reserved. The organic layer was dried over Na2SO4 and concentrated in vacuo to give a crude solid. The combined crude solids were triturated with EtOAc (1×20 mL) then purified by chromatography over SiO2 with MeOH/dichloromethane (gradient: 0%-5% MeOH) to afford 6 mg (27%) of 2-(6-chloro-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (3-oxo-cyclohexyl)-amide as a white solid. MS: [M+H]+=423, 1H NMR (300 MHz, DMSO-d6) δ: 12.89 (br. s., 1H), 9.09 (s, 1H), 8.47 (s, 1H), 8.42 (d, J=8.7 Hz, 1H), 8.16 (d, J=7.6 Hz, 1H), 8.01 (d, J=1.5 Hz, 1H), 7.39 (dd, J=8.7, 1.9 Hz, 1H), 4.23-4.41 (m, 1H), 4.18 (s, 3H), 2.69-2.78 (m, 1H), 2.58 (d, J=10.2 Hz, 1H), 2.42 (dd, J=11.1, 5.9 Hz, 1H), 2.17-2.34 (m, 2H), 1.96-2.08 (m, 1H), 1.80-1.93 (m, 1H), 1.65-1.80 (m, 1H).

1. stirringthe reaction mixture was stirred for an additional 18 h
2. washwashed
3. filtrationThe crude white precipitate was filtered
4. dry with materialThe organic layer was dried over Na2SO4
5. concentrationconcentrated in vacuo
6. customto give a crude solid
7. customwere triturated with EtOAc (1×20 mL)
8. customthen purified by chromatography over SiO2 with MeOH/dichloromethane (gradient: 0%-5% MeOH)