[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]=[C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[N:10]([CH2:19][C:20](O)=[O:21])[N:9]=2)=[CH:4][C:3]=1[CH3:23].CCN(C(C)C)C(C)C.[N:33]1([C:39]2[N:44]=[CH:43][CH:42]=[CH:41][N:40]=2)[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]=[C:11]([C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:10]([CH2:19][C:20]([N:36]3[CH2:37][CH2:38][N:33]([C:39]4[N:40]=[CH:41][CH:42]=[CH:43][N:44]=4)[CH2:34][CH2:35]3)=[O:21])[N:9]=2)=[CH:4][C:3]=1[CH3:23]50 mg 3-(4-fluoro-3-methyl-phenyl)-5-phenyl-pyrazol-1-yl acetic acid was dissolved in 2 mL DMF. 83 mg PFTU and 33 μL DIPEA were added to this solution and the mixture was stirred for 15 min at RT. Then, 25 μL 2-(1-piperazinyl)-pyrimidine was added and stirring was continued for 8 h. Then, 1 mL of a K2CO3 solution (5%) and 10 mL CH2Cl2 were added, the organic phase was separated and washed two times with water. The solvent was removed and the residue was crystallized from ACN to yield 46 mg of the desired compound.
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