[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][NH2:9])=[N:6][CH:7]=1.C(N(CC)CC)C.[CH:17]([N:20]([CH:24]([CH3:26])[CH3:25])[C:21](Cl)=[O:22])([CH3:19])[CH3:18].O>C(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][NH:9][C:21]([N:20]([CH:24]([CH3:26])[CH3:25])[CH:17]([CH3:19])[CH3:18])=[O:22])=[N:6][CH:7]=1
To a solution of (5-fluoro-pyridin-2-yl)-hydrazine (for reference procedure see WO2010/022076; 200 mg, 1.57 mmol) in DCM (15 mL) was added triethylamine (328 μL, 2.35 mmol) followed by N,N-diisopropylcarbamoyl chloride (282 mg, 1.73 mmol). The reaction mixture was heated at 45° C. for 4 h then poured into water and extracted with DCM (×3). The combined organic layers were washed with brine, dried (MgSO4) and concentrated in vacuo. The resultant residue was purified by FCC on silica, using a gradient of 0-100% EtOAc in cyclohexane, to afford the title compound (200 mg, 50%). 1H NMR (400 MHz, CDCl3): 1.30 (12H, d, J=6.8 Hz), 3.80-4.03 (2H, m), 6.17 (1H, s), 6.53 (1H, s), 6.67-6.81 (1H, m), 7.24-7.36-(1H, m), 8.02 (1H, d, J=3.0 Hz).
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