[CH:1]1([NH:4][C:5]2[C:6]([NH2:12])=[CH:7][CH:8]=[C:9]([F:11])[CH:10]=2)[CH2:3][CH2:2]1.[F:13][C:14]1[CH:15]=[C:16]([C:20](O)=[O:21])[CH:17]=[N:18][CH:19]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.C(N(C(C)C)CC)(C)C>ClCCl>[CH:1]1([NH:4][C:5]2[CH:10]=[C:9]([F:11])[CH:8]=[CH:7][C:6]=2[NH:12][C:20]([C:16]2[CH:17]=[N:18][CH:19]=[C:14]([F:13])[CH:15]=2)=[O:21])[CH2:3][CH2:2]1To a solution of the title compound from N2-cyclopropyl-4-fluorobenzene-1,2-diamine (0.065 g, 0.39 mmol) in dichloromethane (1.96 mL) were added 5-fluoropyridine-3-carboxylic acid (0.061 g, 0.43 mmol), EDC (0.082 g, 0.43 mmol), HOBt (0.066 g, 0.43 mmol), and diisopropylethylamine (0.280 mL, 1.56 mmol). The reaction was stirred at room temperature overnight, then diluted with dichloromethane, washed sequentially with water and brine, dried over magnesium sulfate, filtered and concentrated. Purification by flash chromatography on silica gel (30-50% ethyl acetate in hexanes) provided the title compound: LCMS m/z 290.14 [M+H]+; 1H NMR (500 MHz, CDCl3) δ 8.90 (s, 1 H), 8.66 (d, J=2.0 Hz, 1 H), 7.97 (d, J=8.3 Hz, 1 H), 7.48 (br s, 1 H), 7.19 (m, 1 H), 6.92 (d, J=10.9 Hz, 1 H), 6.52-6.49 (m, 1 H), 4.50 (br s, 1 H), 2.47-2.44 (m, 1 H), 0.81-0.77 (m, 2 H), 0.54-0.51 (m, 2 H).
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