N1C=CC=CC=1.ClC(Cl)(O[C:11](=[O:17])OC(Cl)(Cl)Cl)Cl.[CH3:19][C@H:20]1[CH2:25][CH2:24][CH2:23][C@@H:22]([CH3:26])[NH:21]1.C[C@H]1CCC[C@@H](C)N1.C(Cl)(=O)N.CCN(C(C)C)C(C)C.[F:48][C:49]1[CH:50]=[CH:51][C:52]([NH:55][NH2:56])=[N:53][CH:54]=1>C(Cl)Cl>[F:48][C:49]1[CH:50]=[CH:51][C:52]([NH:55][NH:56][C:11]([N:21]2[C@H:22]([CH3:26])[CH2:23][CH2:24][CH2:25][C@@H:20]2[CH3:19])=[O:17])=[N:53][CH:54]=1Pyridine (2.40 mL, 29.7 mmol) was added dropwise to an ice cold suspension of triphosgene (4.42 g, 14.9 mmol) in DCM (30.0 mL). cis-2,6-Dimethylpiperidine (2.00 mL, 14.9 mmol) was added and the reaction stirred for 3 hours, then quenched by dropwise addition of HCl (1M aqueous, 30 mL). The mixture was extracted into DCM (3×). The combined organic layers were washed with brine, dried (MgSO4), filtered and evaporated in vacuo. The product was used in the next reaction without purification. cis-2,6-Dimethylpiperidine-carbamoylchloride (1.79 g, 10.2 mmol) was dissolved in DCM (90.0 mL) and DIPEA (2.42 mL, 13.9 mmol) was added followed by (5-fluoro-pyridin-2-yl)-hydrazine (WO 2010 022076, which is incorporated herein by reference in its entirety, 1.18 g, 9.30 mmol) and the reaction heated to 45° C. overnight. The reaction was cooled and quenched into water. The mixture was extracted into DCM (3×). The combined organic layers were washed with brine, dried (MgSO4), filtered and evaporated in vacuo. The residue was purified by FCC using 0-6% [2M NH3 in MeOH] in DCM to give the title compound (1.38 g, 56%). 1H NMR (300 MHz, CDCl3): 1.29 (6H, d, J 7.1 Hz), 1.48-1.90 (6H m), 4.26 (2H, qn, J 6.9 Hz), 6.39 (1H, d, J 2.3 Hz), 6.50 (1H, d, J 2.3 Hz), 6.74 (1H, dd, J 9.0, 3.6 Hz), 7.27 (1H, ddd, J 8.9, 8.0, 2.9 Hz), 8.03 (1H, d, J 2.9 Hz).
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