N-chloroaniline

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

Procedure: The title compound was prepared using the method described for Compound 481. In this reaction 102 mg (0.2 mmol) of crude 2-(4-chloro-2-phenyl-quinolin-6-yl)-1-cyclohexyl-1H-benzoimidazole-5-carboxylic acid ethyl ester were used. The nucleophile used wasp-chlorophenylamine. Yield: 89 mg.

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

Procedure: To a solution of 2-(4-hydroxy-2-(1H-pyrazol-1-yl)pyrimidin-5-yl)acetic acid, 12-d, (150 mg, 0.68 mmol) and HOBt (101.2 mg, 0.75 mmol) in DMF (5 ml) was added EDC.HCl (144 mg, 0.75 mmol) and DIEPA (264 mg, 2.05 mmol). The solution was stirred at room temperature for 5 mins before the addition of the chlorophenyl amine (0.75 mmol) (Sigma-Aldrich). The mixture was stirred at room temperature for 24 hours. The mixture was then diluted with water and extracted with ethyl acetate. The organic layer was concentrated under vacuum and the residue was purified by silica gel column or Prep-HPLC to give the final compound 12-1. 1H NMR (DMSO-d6, 300 MHz): δ 10.23 (s, 1H), 8.56 (d, 1H), 7.92 (s, 1H), 7.63 (d, 2H), 7.37 (d, 2H), 6.64 (s, 1H), 3.53 (s, 2H). (M+H)+=330.1. extracted with ethyl acetate The organic layer was concentrated under vacuum the residue was purified by silica gel column or Prep-HPLC