Multi-step reaction with 15 steps
1.1: lithium hydroxide / methanol; dichloromethane / 8 h / 20 °C
1.2: pH 1 / Acidic conditions
2.1: O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / dichloromethane / 0.75 h / 20 °C / Inert atmosphere
3.1: palladium 10% on activated carbon; hydrogen / ethanol
4.1: diethylamino-sulfur trifluoride / dichloromethane / 1 h / -78 °C / Inert atmosphere
5.1: potassium carbonate / dichloromethane / -78 - 20 °C / Inert atmosphere
6.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 0.25 h / -20 °C / Inert atmosphere
6.2: 12 h / -20 - 20 °C / Inert atmosphere
7.1: ammonium hydroxide / methanol; water / 20 °C / Sonication
8.1: Lawessons reagent / 1,2-dimethoxyethane / 60 °C / Inert atmosphere
9.1: potassium hydrogencarbonate / 1,2-dimethoxyethane / 16 h / 20 °C / Inert atmosphere
9.2: 3 h / 0 °C / Inert atmosphere
9.3: 3 h / 20 °C / Inert atmosphere
10.1: ammonium hydroxide / methanol; water / 20 °C / Sonication
11.1: Lawessons reagent / 1,2-dimethoxyethane / 60 °C / Inert atmosphere
12.1: potassium hydrogencarbonate / 1,2-dimethoxyethane / 16 h / 20 °C / Inert atmosphere
12.2: 3 h / 0 °C / Inert atmosphere
12.3: 3 h / 20 °C / Inert atmosphere
13.1: lithium hydroxide / methanol; dichloromethane / 8 h / 20 °C
13.2: pH 1 / Acidic conditions
14.1: O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / dichloromethane / 0.75 h / 20 °C / Inert atmosphere
15.1: lithium hydroxide / methanol; dichloromethane / 8 h / 20 °C
15.2: pH 1 / Acidic conditions
With
Lawessons reagent; ammonium hydroxide; diethylamino-sulfur trifluoride; palladium 10% on activated carbon; hydrogen; potassium carbonate; potassium hydrogencarbonate; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; lithium hydroxide;
In
methanol; 1,2-dimethoxyethane; ethanol; dichloromethane; water;
9.1: Hantzsch thiazole synthesis / 9.2: Hantzsch thiazole synthesis / 9.3: Hantzsch thiazole synthesis / 12.1: Hantzsch thiazole synthesis / 12.2: Hantzsch thiazole synthesis / 12.3: Hantzsch thiazole synthesis;
DOI:10.1016/j.tetlet.2012.05.105