[Cl:1][C:2]1[CH:7]=[CH:6][C:5](I)=[CH:4][C:3]=1[C:9]1[N:18]=[CH:17][C:16]2[CH2:15][CH2:14][C:13]3[N:19]=[C:20]([NH:22][C:23](=[O:25])[CH3:24])[S:21][C:12]=3[C:11]=2[N:10]=1.[C:26]([CH:28]1[CH2:33][CH2:32][N:31](C(OC(C)(C)C)=O)[CH2:30][CH2:29]1)#[CH:27].C(N(C(C)C)CC)(C)C.O=O>O1CCCC1.Cl.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cu]I.ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:27]#[C:26][CH:28]2[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]2)=[CH:4][C:3]=1[C:9]1[N:18]=[CH:17][C:16]2[CH2:15][CH2:14][C:13]3[N:19]=[C:20]([NH:22][C:23](=[O:25])[CH3:24])[S:21][C:12]=3[C:11]=2[N:10]=12.0 g (4.0 mmol) N-[8-(2-chloro-5-iod-phenyl)-4,5-dihydro-thiazolo[4,5-h]quinazolin-2-yl]-acetamide are placed in 50 mL tetrahydrofuran under an argon atmosphere and combined with 1.5 g (7 mmol) tert-butyl 4-ethynyl-piperidine-1-carboxylate and 0.5 ml (3 mmol) diisopropylethylamine. The mixture is kept free from oxygen and 78 mg (0.1 mmol) triphenylphosphine palladium(II)-chloride and 21 mg (0.1 mmol) copper(I)-iodide are added. The mixture is stirred for 5 hours at 80° C. After cooling to ambient temperature the reaction mixture is combined with dichloromethane and washed with dilute ammonia solution. The organic phase is dried and evaporated to dryness. The residue is purified by chromatography, corresponding fractions are combined and freeze-dried. The intermediate product obtained is stirred for 2 hours in ethereal hydrochloric acid, suction filtered and dried. Yield: 65 mg (m.p.: 162° C.; MH+=430; RT=3.72; Method A)
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