Br[C:2]1[C:10]2[S:9][C:8]([NH:11][C:12](=[O:16])[NH:13][CH2:14][CH3:15])=[N:7][C:6]=2[CH:5]=[C:4]([C:17]2[CH:18]=[N:19][C:20]([N:23]3[CH2:28][CH2:27][C:26]([CH3:34])([C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH2:25][CH2:24]3)=[N:21][CH:22]=2)[CH:3]=1.[C:35]([C:37]1[N:41]([CH3:42])[CH:40]=[N:39][CH:38]=1)#[CH:36]>C(N(CC)CC)C.CCOC(C)=O.[Cu]I.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>[CH2:14]([NH:13][C:12]([NH:11][C:8]1[S:9][C:10]2[C:2]([C:36]#[C:35][C:37]3[N:41]([CH3:42])[CH:40]=[N:39][CH:38]=3)=[CH:3][C:4]([C:17]3[CH:22]=[N:21][C:20]([N:23]4[CH2:24][CH2:25][C:26]([CH3:34])([C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH2:27][CH2:28]4)=[N:19][CH:18]=3)=[CH:5][C:6]=2[N:7]=1)=[O:16])[CH3:15]Ethyl 1-[5-[7-bromo-2-(ethylcarbamoylamino)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methyl-piperidine-4-carboxylate (150 mg, 0.27 mmol), copper(I) iodide (5 mg, 0.027 mmol) and 5-ethynyl-1-methyl-1H-imidazole (56 μl, 0.54 mmol) were dissolved in triethylamine (2 mL) and DMF (1 mL) and the mixture deoxygenated by bubbling N2 through the solution for 20 min. Pd(PPh3)2Cl2, (19 mg, 0.027 mmol) was added and the reaction heated to 80° C. for 4 h under a N2 atmosphere, at the end of which time LCMS indicated product formation. The reaction was diluted with EtOAc, washed with water then brine and the organic layer dried (MgSO4), filtered and the solvent removed in vacuo to give the desired compound.
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