[H-].[Na+].[NH2:3][C:4]1[N:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2F)[N:7]=[C:6]([C:16]([O:18]CC)=[O:17])[CH:5]=1.[OH-:21].[Na+]>O1CCOCC1>[C:9]1([N:8]2[C:4]([NH:3][C:4]([NH:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)=[O:21])=[CH:5][C:6]([C:16]([OH:18])=[O:17])=[N:7]2)[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1145.3 mg (3.63 mmol, 1.2 Eq) of a 60% suspension of NaH in mineral oil are suspended in 25 ml of dioxane, 700 mg (3.03 mmol) of ethyl 5-amino-1-(2-fluoro-phenyl)-1H-pyrazole-3-carboxylate are added and the resulting mixture is stirred for 10 minutes at RT: Then phenylisocanate (360.6 mg, 3.03 mmol, 1 Eq) is added and the resulting mixture is heated to 80° C. for 5 hours. After cooling 7 ml of 1M NaOH are added and the resulting mixture is stirred overnight at RT. The solvent is evaporated in vacuo and the obtained crude product is subjected to HPLC chromatography. 257 mg (26%) of the pure product are obtained.
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