反应详情

温度

70 °C

A tube was charged with methylamine hydrochloride (7.79 mg, 0.115 mmol) followed by methylamine (2 M in MeOH, 0.058 ml, 0.115 mmol) and NaCNBH3 (14.5 mg, 0.231 mmol). Then, a suspension of N-(5-cyanopyridin-2-yl)-7-(dimethoxymethyl)-6-formyl-3,4-dihydro-1,8-naphthyridine-1(2H)-carboxamide (intermediate 36, 22 mg, 0.058 mmol) in MeOH (1 ml) was added, the tube was sealed and the reaction mixture was stirred at 70° C. for 1 h. The reaction mixture was quenched with water and concentrated until the organic solvents had mostly been removed. Water was added and the mixture was extracted with DCM (3×). The organic phase was then dried over Na2SO4, filtered and evaporated. The crude material was purified by normal phase chromatography (4 g silica gel cartridge, DCM/(DCM/(7 M NH3 in MeOH) 9/1) 100:0 to 50:50) to give the title compound as a yellow resin. (UPLC-MS 3) tR 0.72 min; ESI-MS 397.3 [M+H]+.

1. additionwas added
2. customthe tube was sealed
3. customThe reaction mixture was quenched with water
4. concentrationconcentrated until the organic solvents
5. customhad mostly been removed
6. additionWater was added
7. extractionthe mixture was extracted with DCM (3×)
8. dry with materialThe organic phase was then dried over Na2SO4
9. filtrationfiltered
10. customevaporated
11. customThe crude material was purified by normal phase chromatography (4 g silica gel cartridge, DCM/(DCM/(7 M NH3 in MeOH) 9/1) 100:0 to 50:50)