反应详情

温度

60 °C

To a solution of 2-(3-ethynyl-quinolin-6-yloxy)-N-(1-formyl-cyclobutyl)-2-methylsulfanyl-acetamide (180 mg) from Example 12f, Step 2 described above in a 10/1 mixture of toluene/THF (11 ml) p-toluene sulphonic acid (4 mg) was added followed by MeOH (1.10 ml), at room temperature. The mixture was stirred at 50° C. overnight and 60° C. during 6 hrs, then after cooling to room temperature poured into aq NaHCO3 soln and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulphate anhydrous, filtered and concentrated under reduced pressure. The crude residue was purified by chromatography on silica gel (cyclohexane/ethyl acetate) to give N-(1-dimethoxymethyl-cyclobutyl)-2-(3-ethynyl-quinolin-6-yloxy)-2methylsulfanyl-acetamide as white solid. 1H NMR (CDCl3) δ ppm: 8.84 (1H, d); 8.19 (1H, d); 8.05 (1H, d); 7.46 (1H, dd); 7.23 (1H, d); 6.86 (1H, br s); 5.62 (1H, s); 4.57 (1H, s); 3.51 (3H, s); 3.47 (3H, s); 3.28 (1H, s); 2.47-2.21 (4H, m); 2.21 (3H, 5); 2.01-1.73 (2H, m).

1. additionwas added
2. temperatureafter cooling to room temperature
3. extractionextracted with ethyl acetate
4. washThe combined organic layers were washed with brine
5. dry with materialdried over sodium sulphate anhydrous
6. filtrationfiltered
7. concentrationconcentrated under reduced pressure
8. customThe crude residue was purified by chromatography on silica gel (cyclohexane/ethyl acetate)