反应详情

温度

80 °C

N-(6-(6-chloro-5-(isopropylamino)pyridin-3-yl)benzo[d]thiazol-2-yl)acetamide (123.6 mg, 342.5 μmol) was suspended in MeOH (2.2 ml) and sodium hydroxide (89.90 mg, 2248 μmol) and water (0.44 ml) were added. The reaction flask was fit with a reflux condenser and placed in a preheated oil bath (80° C.), and the reaction was stirred for 1 hour. The reaction was cooled to room temperature, treated with 5 N HCl to neutralize the solution, and allowed to stand overnight. It was then extracted with 10:1 DCM/MeOH, and the organic extracts were combined, concentrated, and purified on a silica gel column (20:1 DCM/MeOH to 15:1 DCM/2 N ammonia in MeOH). Fractions with product collected, concentrated, and treated with Et2O and MeOH. The MeOH washings were decanted, and the solid was collected and dried under high vacuum to afford 6-(6-chloro-5-(isopropylamino)pyridin-3-yl)benzo[d]thiazol-2-amine (18.2 mg, 17% yield). MS (ESI pos. ion) m/z: 319. Calculated exact mass for C15H15ClN4S 318.

1. customThe reaction flask was fit with a reflux condenser
2. customplaced in a preheated oil bath
3. temperatureThe reaction was cooled to room temperature
4. waitto stand overnight
5. extractionIt was then extracted with 10:1 DCM/MeOH
6. concentrationconcentrated
7. custompurified on a silica gel column (20:1 DCM/MeOH to 15:1 DCM/2 N ammonia in MeOH)
8. customFractions with product collected
9. concentrationconcentrated
10. additiontreated with Et2O and MeOH
11. customThe MeOH washings were decanted
12. customthe solid was collected
13. customdried under high vacuum