[Cl:1][C:2]1[C:3]([CH3:15])=[N:4][N:5](CC(O)=O)[C:6]=1[C:7]([F:10])([F:9])[F:8].[C:16](Cl)(=[O:20])[C:17](Cl)=O.[F:22][C:23]1[CH:28]=[CH:27][C:26]([N:29]2[CH:33]=[C:32]([NH2:34])[CH:31]=[N:30]2)=[CH:25][CH:24]=1.CCN(CC)CC>C(Cl)Cl.CN(C=O)C.O>[Cl:1][C:2]1[C:6]([C:7]([F:8])([F:9])[F:10])=[N:5][N:4]([CH2:17][C:16]([NH:34][C:32]2[CH:31]=[N:30][N:29]([C:26]3[CH:27]=[CH:28][C:23]([F:22])=[CH:24][CH:25]=3)[CH:33]=2)=[O:20])[C:3]=1[CH3:15]
To a mixture of 2-[4-chloro-3-methyl-5-(trifluoromethyl)pyrazol-1-yl]acetic acid (0.150 g, 0.62 mmol) in CH2Cl2 (2 mL) was added oxalyl chloride (0.15 mL, 1.75 mmol) and DMF (1 drop). The mixture was stirred for 30 min at room temperature and was then concentrated in vacuo. The solid obtained was transferred to another flask containing 1-(4-fluorophenyl)pyrazol-4-amine (0.080 g, 0.45 mmol) and NEt3 (0.25 mL, 1.8 mmol) in CH2Cl2 (3 mL). The mixture was stirred for 30 min at room temperature, treated with water (50 mL), and extracted with ethyl acetate (50 mL). The organic layer was separated, dried over anhydrous sodium sulfate, concentrated in vacuo, and purified by flash chromatography (SiO2, 0-50% EtOAc/hexanes gradient elution) to give the title compound as a white solid (0.084 g, 47%). 1H NMR (400 MHz CDCl3) δ 8.40 (s, 1H), 7.71 (s, 1H), 7.69 (m, 2H), 7.19 (dd, J=8.4, 8.4 Hz, 2H), 5.07 (s, 2H), 2.34 (s, 3H); MS: (ES) m/z calculated for C16H12ClF4N5O [M+H]+ 402.0, found 402.0.
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