Multi-step reaction with 10 steps
1.1: formic acid / tetrahydrofuran; water / 96 h
2.1: caesium carbonate; 1-{3,5-bis(trifluoromethyl)phenyl}-3-{(1R,2R)-2-(dimethylamino)cyclohexyl}thiourea / water; toluene / 144 h / -20 - 0 °C
3.1: formic acid / 20 h / 0 - 5 °C
4.1: HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 2 h / 0 °C
5.1: formic acid / 120 h / 20 °C
6.1: triethylamine / tetrahydrofuran / 4 h / 60 °C
7.1: triethylamine / dichloromethane / 2 h
8.1: palladium 10% on activated carbon; hydrogen / methanol; ethyl acetate / 16 h
9.1: caesium carbonate / N,N-dimethyl-formamide / 5 h / 20 °C
10.1: barium hydroxide octahydrate / methanol; tert-butyl alcohol / 1 h / 20 °C
10.2: 21 h / 5 - 20 °C
With
formic acid; barium hydroxide octahydrate; palladium 10% on activated carbon; hydrogen; caesium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; HATU; 1-{3,5-bis(trifluoromethyl)phenyl}-3-{(1R,2R)-2-(dimethylamino)cyclohexyl}thiourea;
In
tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; toluene; tert-butyl alcohol;