[N:1]([C:4]([O:6][CH2:7][CH3:8])=[O:5])=[C:2]=S.[F:9][C:10]1[CH:11]=[C:12]([CH:14]=[C:15]([F:17])[CH:16]=1)[NH2:13].C(N(CC)CC)C.[NH:25]1[CH:29]=[C:28]([C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH:27]=[N:26]1.CCN=C=NCCCN(C)C.Cl>C(Cl)Cl>[CH2:33]([O:32][C:30]([C:28]1[CH:29]=[N:25][N:26]([C:2](=[N:13][C:12]2[CH:11]=[C:10]([F:9])[CH:16]=[C:15]([F:17])[CH:14]=2)[NH:1][C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH:27]=1)=[O:31])[CH3:34]Ethyl isothiocyanatoformate (0.68 mL, 5.8 mmol) was added to a solution of 3,5-difluoroaniline (0.680 g, 5.27 mmol) and DCM (26 mL). After 3 h, triethylamine (2.20 mL, 15.8 mmol) was added to the reaction mixture, followed by ethyl pyrazole-4-carboxylate (0.812 g, 5.79 mmol), and EDCl (1.21 g, 6.32 mmol). After 1.5 h, the reaction mixture was diluted with DCM (25 mL), washed with water (3×30 mL) and with brine (50 mL), dried (MgSO4), and concentrated. The residue was purified by FCC (3-45% EtOAc/hexanes) to yield the titled compound (0.323 g, 17% yield). MS (ESI/Cl): mass calcd. for C16H16F2N4O4, 366.1; m/z found, 367.1 [M+H]+.
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