[NH2:1][C:2]([CH3:7])([CH2:5][F:6])[C:3]#[N:4].ON1C2N=CC=CC=2N=N1.CN(C)CCCN=C=NCC.Cl.[I:30][C:31]1[CH:32]=[N:33][C:34]2[C:39]([CH:40]=1)=[CH:38][C:37]([O:41][CH:42]([S:46][CH3:47])[C:43](O)=[O:44])=[CH:36][C:35]=2[CH3:48]>CN(C)C=O.[Cl-].[Na+].O.C(N(CC)CC)C>[C:3]([C:2]([NH:1][C:43](=[O:44])[CH:42]([O:41][C:37]1[CH:38]=[C:39]2[C:34](=[C:35]([CH3:48])[CH:36]=1)[N:33]=[CH:32][C:31]([I:30])=[CH:40]2)[S:46][CH3:47])([CH3:7])[CH2:5][F:6])#[N:4]
To a solution of 2-amino-3-fluoro-2-methylpropionitrile (315 mg) in dry dimethylformamide (20 mL) were added triethylamine (0.43 mL), 1-hydroxy-7-azabenzotriazole (420 mg), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide.HCl (591 mg), then (3-iodo-8-methyl-quinolin-6-yloxy)-methylsulfanyl-acetic acid (1.2 g). The reaction mixture was stirred at room temperature for 18 hours. The mixture was poured over brine and extracted twice with ethyl acetate (thrice). The organic layer was washed with water then with brine, dried over sodium sulphate, filtered and concentrated under reduced pressure. The crude was purified by chromatography eluting with cyclohexane/ethyl acetate (3:2 by volume), to give N-(1-cyano-2-fluoro-1-methyl-ethyl)-2-(3-iodo-8-methyl-quinolin-6-yloxy)-2-methylsulfanyl-acetamide (906 mg) as a solid.
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