[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]([CH2:11][N:12]2[C:16]([C:17]([OH:19])=O)=[CH:15][C:14]([O:20][CH2:21][CH2:22][O:23][CH2:24][CH2:25][O:26][CH3:27])=[N:13]2)=[O:10])=[N:6][CH:7]=1.Cl.[CH:29]([N:32]1[CH2:37][CH2:36][CH:35]([NH2:38])[CH2:34][CH2:33]1)([CH3:31])[CH3:30].C1N(P(Cl)(N2C(=O)OCC2)=O)C(=O)OC1>C(Cl)Cl.CCN(CC)CC>[CH:29]([N:32]1[CH2:37][CH2:36][CH:35]([NH:38][C:17]([C:16]2[N:12]([CH2:11][C:9](=[O:10])[NH:8][C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][N:6]=3)[N:13]=[C:14]([O:20][CH2:21][CH2:22][O:23][CH2:24][CH2:25][O:26][CH3:27])[CH:15]=2)=[O:19])[CH2:34][CH2:33]1)([CH3:31])[CH3:30]To 310 mg 2-[(5-Chloro-pyridin-2-ylcarbamoyl)-methyl]-5-[2-(2-methoxy-ethoxy)-ethoxy]-2H-pyrazole-3-carboxylic acid in 5 ml DCM and 0.3 ml NEt3, 110 mg 1-Isopropyl-piperidin-4-ylamine hydrochloride and 197 mg BOP-CL were added at RT and the mixture was stirred for 16 h. The mixture was concentrated under reduced pressure and the residue was purified by preparative HPLC (C18 reverse phase column, elution with a H2O/MeCN gradient with 0.1% TFA). The fractions containing the product were evaporated and lyophilized to yield a white solid.
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