(2-amino-5-chloro-4-fluorophenyl)-phenylmethanone

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title compound was prepared in analogy to example 101 step B from (2-amino-5-chloro-4-fluoro-phenyl)-phenyl-methanone (prepared as described in example 105 step D) and 3-cyclohexyl-3-oxo-propionitrile (prepared as described in example 110 step A). Off-white solid. MS (ESI): 365.4 (M+H)+.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title compound was prepared in analogy to example 102 step A from (2-amino-5-chloro-4-fluoro-phenyl)-phenyl-methanone (prepared as described in example 105 step D) and 2-(1H-tetrazol-5-yl)acetic acid. Off-white solid. MS (ESI): 342.4 (M+H)+.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title compound was prepared in analogy to example 101 step B from (2-amino-5-chloro-4-fluoro-phenyl)-phenyl-methanone (prepared as described in example 105 step D) and 4-ethyl-3-oxo-hexanenitrile (prepared as described in example 101 step A). Off-white solid. MS (ESI): 353.4 (M+H)+.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title compound was prepared in analogy to example 101 step B from (2-amino-5-chloro-4-fluoro-phenyl)-phenyl-methanone and 3-cyclopentyl-3-oxo-propionitrile. Off-white solid. MS (ESI): 351.4 (M+H)+.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of phenylmagnesium bromide (7.18 ml, 3M solution in diethyl ether, 21.5 mmol) in diethyl ether (15 ml) was added to a solution of 2-amino-5-chloro-4-fluoro-benzonitrile (1225 mg, 7.18 mmol) in diethyl ether (20 ml) at 0° C. The reaction mixture was then stirred at reflux for 2 h, cooled to room temperature and quenched carefully by addition of 2N HCl (˜40 ml). The mixture was heated to 55° C. for 3 h and then cooled to room temperature again. 3N NaOH (˜20 ml) was added carefully at 0° C. to adjust the pH to 9. The mixture was extracted with EtOAc and the combined extracts were washed with brine, dried with Na2SO4 and evaporated. The remaining residue was purified by column chromatography (silica gel, heptane/EtOAc 95:5-90:10) to afford the title compound (1667 mg, 93%) as yellow solid. MS (ESI): 250.3 (M+H)+. at reflux for 2 h quenched carefully by addition of 2N HCl (˜40 ml) The mixture was heated to 55° C. for 3 h cooled to room temperature again 3N NaOH (˜20 ml) was added carefully at 0° C. The mixture was extracted with EtOAc the combined extracts were washed with brine dried with Na2SO4 evaporated The remaining residue was purified by column chromatography (silica gel, heptane/EtOAc 95:5-90:10)