[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([CH:11]=O)[CH:9]=2)[NH:4][N:3]=1.[O:13]1[CH2:17][C:16](=O)[CH2:15][C:14]1=[O:19].[NH2:20][C:21]([C:25]([F:28])([F:27])[F:26])=[CH:22][C:23]#[N:24].Cl>C(O)CCCC.O>[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([CH:11]3[C:22]([C:23]#[N:24])=[C:21]([C:25]([F:28])([F:27])[F:26])[NH:20][C:16]4[CH2:17][O:13][C:14](=[O:19])[C:15]3=4)[CH:9]=2)[NH:4][N:3]=1100 mg (0.624 mmol) 3-methyl-1H-indazole-5-carbaldehyde (Example 1A) and 62.5 mg (0.624 mmol) furan-2,4(3H,5H)-dione were heated up to reflux in 1-pentanol (3 ml) for 1 h. After addition of 425 mg (3.120 mmol) 3-amino-4,4,4-trifluorobut-2-enenitrile [A. W. Lutz, U.S. Pat. No. 3,635,977], the reaction mixture was stirred at 100° C. for further 4 h. Then, conc. hydrochloric acid (115 μl) and water (350 μl) were added, and the mixture was stirred at 100° C. for another 1 h. After cooling, the mixture was directly purified by RP-HPLC (acetonitrile/water+0.1% TFA gradient) to give 33 mg (14% of th.) of the title compound.
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