n-hexyl lithium in tetrahydrofuran T=-8 - 10°C; Product distribution / selectivity;

1: in tetrahydrofuran; hexane T=10°C; 2: With sodium hydrogencarbonate; sodium carbonate in tetrahydrofuran; hexane; water T=5 - 20°C; 12 h; Product distribution / selectivity;

1: dimethyl amine With n-hexyl lithium in tetrahydrofuran; hexane T=8 - 12°C; 3 h; 2: N-(5-chloro(2-pyridyl)){2-[(4-cyanophenyl)carbonylamino]-5-methoxyphenyl}-carboxamide in tetrahydrofuran; hexane T=-12 - -8°C; 3: With sodium hydrogencarbonate; sodium carbonate in water T=-8 - 25°C;

hydrogenchloride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride in isobutyramide; water

1: With hydrogenchloride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride in N,N-dimethyl acetamide; water 2: With sodium carbonate in N,N-dimethyl acetamide; water T=22 - 30°C; Product distribution / selectivity;

1.1: pyridine / acetonitrile / 19 - 25 °C / Industry scale 1.2: 19 - 28 °C / Industry scale 1.3: 12 - 30 °C / Industry scale 2.1: hydrogen / platinum on carbon / dichloromethane / 16.5 h / 25 - 31 °C / 1551.49 Torr / Industry scale 3.1: hydrogenchloride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / water; N,N-dimethyl acetamide 3.2: 22 - 30 °C View Scheme

1.1: hydrogen / platinum on carbon / dichloromethane / 16.5 h / 25 - 31 °C / 1551.49 Torr / Industry scale 2.1: hydrogenchloride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / water; N,N-dimethyl acetamide 2.2: 22 - 30 °C View Scheme

1.1: pyridine / acetonitrile / 19 - 25 °C / Industry scale 1.2: 19 - 28 °C / Industry scale 1.3: 12 - 30 °C / Industry scale 2.1: hydrogen / platinum on carbon / dichloromethane / 16.5 h / 25 - 31 °C / 1551.49 Torr / Industry scale 3.1: hydrogenchloride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / water; N,N-dimethyl acetamide 3.2: 22 - 30 °C View Scheme

in tetrahydrofuran; hexane T=0 - 20°C;

1.1: sulfuric acid / 12 h / Reflux 2.1: hydrogenchloride / 0 - 20 °C 3.1: ethanol / 4 h / Reflux 4.1: lithium hydroxide hydrate / water; tetrahydrofuran / 6 h 4.2: pH 3 - 4 5.1: hydrogenchloride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / water; N,N-dimethyl acetamide 5.2: 22 - 30 °C View Scheme