反应详情

温度

100 °C

A mixture of 3,8-dimethyl-[1,2,4]triazolo[4,3-a]pyridin-6-amine (Step 67.4) (2 g, 12.33 mmol), 4-chlorobenzaldehyde (1.576 g, 11.21 mmol) and ethyl 2,4-dioxopentanoate (1.773 g, 11.21 mmol) in acetic acid (10 mL) was stirred for 2 hr at 100° C. The reaction mixture was concentrated, diluted with CH2Cl2/1N NaOH and extracted with CH2Cl2. The combined organic layers were dried over Na2SO4, evaporated and discarded as they contained no desired product. The aqueous was acidified to pH 3 with 6N HCl and extracted with CH2Cl2. The combined organic extracts were dried over Na2SO4 and concentrated to afford the title compound (3.88 g, 8.80 mmol, 79% yield) as a beige foam. tR: 0.70 min (LC-MS 2); ESI-MS: 397 [M+H]+ (LC-MS 2); 1H NMR (400 MHz, DMSO-d6) δ ppm 2.36 (s, 3H) 2.44 (s, 3H) 2.63 (s, 3H) 6.14 (s, 1H) 7.27 (d, J=8.44 Hz, 2H) 7.33-7.40 (m, 3H) 8.53 (s, 1H).

1. concentrationThe reaction mixture was concentrated
2. additiondiluted with CH2Cl2/1N NaOH
3. extractionextracted with CH2Cl2
4. dry with materialThe combined organic layers were dried over Na2SO4
5. customevaporated
6. extractionextracted with CH2Cl2
7. dry with materialThe combined organic extracts were dried over Na2SO4
8. concentrationconcentrated