1: (3R,6S)-3-amino-6-(2,3-difluorophenyl)-1-(2,2,2-trifluoroethyl)azepan-2-one; chloroformic acid 4-nitrophenyl ester With triethylamine in tetrahydrofuran T=0°C; 0.5 h; 2: 2-oxo-1-(4-piperidinyl)-2,3-dihydro-1H-imidazo[4,5-b]pyridine dihydrochloride With triethylamine in tetrahydrofuran; dichloromethane T=0 - 20°C; 48 h;

1: (3R,6S)-3-amino-6-(2,3-difluorophenyl)-1-(2,2,2-trifluoroethyl)azepan-2-one; chloroformic acid 4-nitrophenyl ester With triethylamine in tetrahydrofuran T=0°C; 2: 2-oxo-1-(4-piperidinyl)-2,3-dihydro-1H-imidazo[4,5-b]pyridine dihydrochloride With triethylamine in tetrahydrofuran; chloroform T=25°C;

1: With hydrogenchloride in 1,4-dioxane; water T=85°C; 12 h; 2: With sodium hydroxide in 1,4-dioxane; tert-butyl methyl ether; water pH=8 - 10;

1.1: 1,4-dioxane; water / 0.25 h / Inert atmosphere 1.2: 6 h / 20 - 35 °C 2.1: hydrogen / palladium 10 on activated carbon / ethanol / 36 h / 2844.39 Torr 3.1: 1-hydroxy-7-aza-benzotriazole; triethylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 1 h 4.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / -35 °C 4.2: 2.5 h / -35 °C 5.1: trifluoroacetic acid / dichloromethane / 0.5 h View Scheme

1.1: diisobutylaluminium hydride / toluene; diethyl ether / 0.58 h / -78 - -65 °C 1.2: 0.5 h / -65 - 20 °C 2.1: N,N,N',N'-tetramethylguanidine / toluene / 0.5 h / 0 °C 2.2: 1.5 h / 0 - 20 °C 3.1: 1,4-dioxane; water / 0.25 h / Inert atmosphere 3.2: 6 h / 20 - 35 °C 4.1: hydrogen / palladium 10 on activated carbon / ethanol / 36 h / 2844.39 Torr 5.1: 1-hydroxy-7-aza-benzotriazole; triethylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 1 h 6.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / -35 °C 6.2: 2.5 h / -35 °C 7.1: trifluoroacetic acid / dichloromethane / 0.5 h View Scheme

1.1: N,N,N',N'-tetramethylguanidine / toluene / 0.5 h / 0 °C 1.2: 1.5 h / 0 - 20 °C 2.1: 1,4-dioxane; water / 0.25 h / Inert atmosphere 2.2: 6 h / 20 - 35 °C 3.1: hydrogen / palladium 10 on activated carbon / ethanol / 36 h / 2844.39 Torr 4.1: 1-hydroxy-7-aza-benzotriazole; triethylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 1 h 5.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / -35 °C 5.2: 2.5 h / -35 °C 6.1: trifluoroacetic acid / dichloromethane / 0.5 h View Scheme

1.1: hydrogen / palladium 10 on activated carbon / ethanol / 36 h / 2844.39 Torr 2.1: 1-hydroxy-7-aza-benzotriazole; triethylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 1 h 3.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / -35 °C 3.2: 2.5 h / -35 °C 4.1: trifluoroacetic acid / dichloromethane / 0.5 h View Scheme

1.1: dichloromethane; hexane; methanol / 1 h / 0 °C 1.2: 24 h / 20 °C 2.1: diisobutylaluminium hydride / toluene; diethyl ether / 0.58 h / -78 - -65 °C 2.2: 0.5 h / -65 - 20 °C 3.1: N,N,N',N'-tetramethylguanidine / toluene / 0.5 h / 0 °C 3.2: 1.5 h / 0 - 20 °C 4.1: 1,4-dioxane; water / 0.25 h / Inert atmosphere 4.2: 6 h / 20 - 35 °C 5.1: hydrogen / palladium 10 on activated carbon / ethanol / 36 h / 2844.39 Torr 6.1: 1-hydroxy-7-aza-benzotriazole; triethylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 1 h 7.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / -35 °C 7.2: 2.5 h / -35 °C 8.1: trifluoroacetic acid / dichloromethane / 0.5 h View Scheme

1.1: 1-hydroxy-7-aza-benzotriazole; triethylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 1 h 2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / -35 °C 2.2: 2.5 h / -35 °C 3.1: trifluoroacetic acid / dichloromethane / 0.5 h View Scheme

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / -35 °C 1.2: 2.5 h / -35 °C 2.1: trifluoroacetic acid / dichloromethane / 0.5 h View Scheme