Reacción #1591149

Ecuación de reacción

sodium bicarbonate

tert-butyl N-(4-[[(3R)-3-(2-hydroxyethyl)-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(8),2(6),9,11-tetraen-12-yl]oxy]cyclohexyl)-N-methylcarbamate

Hydrochloric acid

→

2-[(3R)-12-[[4-(methylamino)cyclohexyl]oxy]-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(8),2(6),9,11-tetraen-3-yl]ethan-1-ol

Rendimiento 77.2%

Disolventes

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroplease refer to the experimental procedure for the synthesis of compound Example 34
2. 2
   OtroA 50-mL round-bottom flask, purged
3. 3
   Temperaturamaintained with an inert atmosphere of nitrogen
4. 4
   Extracciónextracted with dichloromethane
5. 5
   LavadoThe organic layer was washed with brine
6. 6
   Secadodried over anhydrous sodium sulfate
7. 7
   Concentraciónconcentrated under vacuum

Procedimiento

For the preparation of the starting material compound 34.2, please refer to the experimental procedure for the synthesis of compound Example 34. A 50-mL round-bottom flask, purged and maintained with an inert atmosphere of nitrogen, was charged with a solution of tert-butyl N-(4-[[(3R)-3-(2-hydroxyethyl)-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(8),2(6),9,11-tetraen-12-yl]oxy]cyclohexyl)-N-methylcarbamate (197 mg, 0.44 mmol, 1.00 equiv) in dichloromethane (15 mL). Hydrochloric acid (conc., 0.5 mL) was added at 0° C. and the resulting solution was stirred for 2 h at room temperature. The pH value of the solution was adjusted to 10 with aqueous sodium bicarbonate (sat.) and extracted with dichloromethane. The organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated under vacuum to give 2-[(3R)-12-[[4-(methylamino)cyclohexyl]oxy]-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(8),2(6),9,11-tetraen-3-yl]ethan-1-ol (118 mg, 77%) as a yellow solid. MS (ES): m/z 348[M+H]+.

Fuente