Phenylacetylene → 5-Chloro-2-ethyl-9-methyl-13-(2-phenylethyl)-2,4,9,15-tetraazatricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3,5,7,12,14-hexaen-10-one

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2-Chloro-5,11-dihydro-11-ethyl-5-methyl-8-phenylethynyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one (0.33 g) was prepared from 2-chloro-5,11-dihydro-11-ethyl-8-iodo-5-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one and phenylacetylene by a procedure analogous to that described in Example 42a. Hydrogenation as described in Example 42b afforded 0.18 g of the title compound as white needles, m.p. 128°-129.5° C.

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