[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([NH:7][C:8](=[N:16][C:17]#[N:18])OC2C=CC=CC=2)[CH:2]=1.[C:19]1([CH:25]([NH2:28])[CH2:26][CH3:27])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.CN1CCOCC1.C(O)(C)C>CCOC(C)=O.CO>[C:17]([N:16]=[C:8]([NH:28][CH:25]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:26][CH3:27])[NH:7][C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1)#[N:18]
A stirred mixture of N-(3-pyridyl)-N'-cyano-O-phenylisourea (see, Example 5 for procedure) (13.93 g, 0.05836 mol), 1-phenylpropylamine (8.68 g, 0.0642 mol), N-methylmorpholine (139 mL) and isopropanol (92.9 mL) was refluxed, under nitrogen, for 18 hours. The reaction was complete by TLC with 10% MeOH-1% NH4OH-CHCl3. Concentration of the reaction mixture gave a residue that was mixed with EtOAc and concentrated several times until the product crystallized. The solid was boiled twice with small portions of EtOAc; each time the mixture was cooled and the liquid decanted. The resulting solid was crystallized from MeOH-EtOAc to give 7.87 g (43.8%) of product: mp 155°-156° C.
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