Cl.[NH2:2][C:3]1([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:7][CH:6]=[CH:5][CH2:4]1.C([O-])(O)=O.[Na+].CN1CCOCC1.[N:26]1[CH:31]=[CH:30][CH:29]=[C:28]([NH:32][C:33](=[N:41][C:42]#[N:43])OC2C=CC=CC=2)[CH:27]=1>C(O)CC.CCOC(C)=O>[C:42]([N:41]=[C:33]([NH:2][C:3]1([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:4][CH:5]=[CH:6][CH2:7]1)[NH:32][C:28]1[CH:27]=[N:26][CH:31]=[CH:30][CH:29]=1)#[N:43]A stirred mixture of the product from Step 4 (0.537 g, 2.74 mmol) and EtOAc was mixed with enough aqueous NaHCO3 to give a solution and the aqueous layer was extracted with EtOAc; the EtOAc extract was dried (MgSO4) and concentrated. A solution of the residue in -propanol (25 ml) was treated with N-methylmorpholine (0.75 ml, 6.86 mmol) and N-(3- pyridyl)-N'-cyano-O-phenylisourea (see, Example 5 for procedure) (0.98 g, 4.12 mmol) and refluxed under N2 for 16.75 hours. The cooled reaction mixture was concentrated in vacuo and the residue was chromatographed on silica gel with 1.5% MeOH--0.15% NH4OH--CH2Cl2. The product was crystallized from EtOAc to give 3 which had m.p. 155.5°-157° C.
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