反应详情

A solution of N-(4-chlorobenzyl)-4-hydroxy-2-(3-hydroxy-1-propynyl)-thieno[2,3-b]pyridine-5-carboxamide (Example No.5) (0.300 g) in 1/1 CH2Cl2/CH3OH (70 mL) is hydrogenated over 10% Pd/C (90 mg) at 35 psi. After 3 h, an additional 90 mg of 10% Pd/C is added, and the solution is hydrogenated at 35 psi for 1 h. The reaction mixture is filtered through a Celite pad, and the filtrate is concentrated in vacuo. The resulting pale orange solid is purified via column chromatography (CH2Cl2:CH3OH; 98:2, 95:5). Fractions homogeneous by TLC are combined and concentrated in vacuo to yield and off-white solid which is recrystallized from ethanol to yield 0.083 g (27%) of the title compound as a white, crystalline solid.

1. waitthe solution is hydrogenated at 35 psi for 1 h
2. filtrationThe reaction mixture is filtered through a Celite pad
3. concentrationthe filtrate is concentrated in vacuo
4. customThe resulting pale orange solid is purified via column chromatography (CH2Cl2:CH3OH; 98:2, 95:5)
5. concentrationconcentrated in vacuo
6. customto yield
7. customoff-white solid which is recrystallized from ethanol