[CH3:1][N:2]1[CH:6]=[C:5]([C:7]([OH:9])=O)[CH:4]=[N:3]1.CCN(CC)CC.Cl.[F:18][CH2:19][CH2:20][NH:21][CH3:22]>CN(C=O)C>[F:18][CH2:19][CH2:20][N:21]([CH3:22])[C:7]([C:5]1[CH:4]=[N:3][N:2]([CH3:1])[CH:6]=1)=[O:9]Methyl-1H-pyrazole-4-carboxylic acid (1.0 g, 7.93 mmol) was combined with DMF (10.0 ml) to give a colorless solution. Et3N (3.3 ml, 23.8 mmol) and 2-(1H-benzo[d][1,2,3]triazol-1-yl)-1,1,3,3-tetramethylisouronium tetrafluoroborate (TBTU, 2.8 g, 8.72 mmol) were added and the reaction mixture was stirred at RT for 1 h. 2-Fluoroethyl-methylamine hydrochloride (991 mg, 8.72 mmol) was added and stirring was continued overnight. DMF was removed under HV and the crude product (5.93 g brown oil) was purified by chromatography with a 50 g SiO2—NH2 cartridge (CH2Cl2/MeOH 95:5). The resulting product was dried under HV at RT for 48 h. Yellow oil (1.40 g, 92%); MS: m/z=186.1 [M+H]+.
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