[CH2:1]([NH:8][C:9](=[O:12])[CH2:10]Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.[F:22][C:23]1[CH:29]=[CH:28][C:26]([NH2:27])=[C:25]([CH3:30])[CH:24]=1>CN(C=O)C>[CH2:1]([NH:8][C:9](=[O:12])[CH2:10][NH:27][C:26]1[CH:28]=[CH:29][C:23]([F:22])=[CH:24][C:25]=1[CH3:30])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1A mixture of N-benzyl-2-chloroacetamide (17.8 g), DIPEA (19.5 mL) and 4-fluoro-2-methyl-aniline (10.6 mL) in anhydrous DMF (174 mL) was stirred at 100° C. for 40 hours under a Nitrogen atmosphere. After cooling to r.t., the dark solution was partitioned between AcOEt (200 mL) and water (200 mL). The separated aqueous phase was extracted with further AcOEt (3×200 mL). The combined organic extracts were washed with water (200 mL), dried and concentrated in vacuo. The residue was purified by flash chromatography (CH/AcOEt 2:8) to give a dark solid, which was triturated with CH to give the title compound as a beige solid (16.2 g).
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