[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]([NH:34][CH3:35])[CH:31]=[N:30]2)=[CH:25][CH:24]=1.CCN(CC)CC>C(Cl)Cl.CN(C=O)C>[Cl:1][C:2]1[C:6]([C:7]([F:8])([F:9])[F:10])=[N:5][N:4]([CH2:17][C:16]([N: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)[CH3:35])=[O:20])[C:3]=1[CH3:15]
To a solution of 2-[4-chloro-3-methyl-5-(trifluoromethyl)pyrazol-1-yl]acetic acid (0.070 g, 0.29 mmol) in CH2Cl2 (2 mL) was added oxalyl chloride (0.10 mL, 1.16 mmol) and DMF (1 drop). The mixture was stirred for 30 min at room temperature and concentrated in vacuo. The solid obtained was transferred to another flask containing 1-(4-fluorophenyl)-N-methylpyrazol-4-amine (0.056 g, 0.29 mmol) and NEt3 (0.20 mL, 1.4 mmol) in CH2Cl2 (3 mL). The reaction mixture was stirred for 30 min at room temperature, quenched 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/CH2Cl2 gradient elution) to give the title compound (0.045 g, 37%). 1H NMR (400 MHz, CDCl3) δ 8.01 (s, 1H), 7.70 (s, 1H), 7.64 (m, 2H), 7.17 (dd, J=8.4, 8.4 Hz, 2H), 4.80 (s, 2H), 3.28 (s, 3H); MS: (ES) m/z calculated for C17H14ClF4N5O [M+H]+ 416.1, found 416.1.
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