N1C2C(=N[C:7](=[O:16])[C:8]3[CH:15]=[CH:14]C=NC=3N=2)C=CC=1.I[C:18]1[CH:19]=NN[CH:22]=1.C(N(CC)CC)C.CN(C)C=[O:33]>C(OCC)(=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[C:19]([O:16][CH2:7][CH3:8])(=[O:33])[CH3:18].[CH:18]([O:33][CH:15]([CH3:14])[CH3:8])([CH3:19])[CH3:22]
A mixture of 5,11-dihydro-11-ethyl-8-ethynyl-4-methyl-(-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one (obtained by procedures analogous to those described in Example 51) (147 mg), 4-iodopyrazole (199 mg), bis(triphenylphosphine)palladium(II) chloride (22 mg), copper(I) iodide (21 mg), and triethylamine (2 mL) in 4 mL of N,N-dimethylformamide was heated at 100° C. in a sealed tube for 40 min. The reaction mixture was diluted with ethyl acetate and washed with water. The organic layer was dried over sodium sulfate and concentrated. The crude residue was dissolved in 60 mL of methanol and hydrogenated at 50 p.s.i. over 10% palladium on carbon (70 mg). After 24 hours, the reaction mixture was filtered and concentrated. The residue was purified by flash chromatography, eluting with methanol/ethyl acetate, to afford the compound of Example 52, m.p. 184°-187° C. (ethyl acetate/isopropyl ether), and the compound of Example 53, m.p. 199°-201° C. (ethyl acetate/hexanes).
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