[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7](O)=O)[N:2]=1.ON1C2C=CC=CC=2N=N1.[H-].CN(C)CCCN=C=NCC.[C:32]([C:34]1[CH:66]=[CH:65][CH:64]=[CH:63][C:35]=1[O:36][C:37]1[C:51]([O:52][C:53]2[CH:58]=[CH:57][C:56]([S:59]([CH3:62])(=[O:61])=[O:60])=[CH:55][CH:54]=2)=[CH:50][C:40]2[NH:41]C(C3C=CC=CN=3)=[N:43][C:39]=2[CH:38]=1)#[N:33]>C(OCC)(=O)C.CN1CCCC1=O>[C:32]([C:34]1[CH:66]=[CH:65][CH:64]=[CH:63][C:35]=1[O:36][C:37]1[C:51]([O:52][C:53]2[CH:54]=[CH:55][C:56]([S:59]([CH3:62])(=[O:60])=[O:61])=[CH:57][CH:58]=2)=[CH:50][C:40]2[NH:41][C:7]([C:3]3[N:2]=[N:1][CH:6]=[CH:5][CH:4]=3)=[N:43][C:39]=2[CH:38]=1)#[N:33]3.3 mg of pyridazine-3-carboxylic acid, 15 mg of 1-hydroxybenzotriazole and 15 mg of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide monohydride were added in order to an N-methylpyrrolidone (0.3 ml) solution of 15 mg of 4-(2-cyano-phenoxy)-5-(4-methanesulfonyl-phenoxy)-benzene-1,2-diamine obtained in Example 17, and the reaction liquid was stirred overnight at room temperature. The reaction liquid was diluted with ethyl acetate, and washed with saturated sodium bicarbonate solution, and the solvent was evaporated away under reduced pressure. The resulting residue was dissolved in 0.2 ml of N-methylpyrrolidone, and 5 mg of ytterbium trifluoromethanesulfonate was added to it, and the reaction liquid was stirred overnight at 140° C. The reaction mixture was purified through reversed-phase middle-pressure liquid chromatography [ODS-AS-360-CC (by YMC), mobile phase: water-acetonitrile-0.1% trifluoroacetic acid]. The solvent of the resulting fraction was evaporated away under reduced pressure to obtain the entitled compound as a brown solid.
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