Cl.[CH2:2]([NH:9][CH2:10][CH2:11][NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH:19]([N:22](C(C)C)CC)(C)C.[C:28]([C:30](=C)C#N)#N>CN(C=O)C>[CH2:2]([N:9]1[CH2:30][CH2:28][N:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:11]([C:19]#[N:22])[CH2:10]1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1A solution of 14 (5.07 g, 17.0 mmol) and diisopropylethylamine (4.97 g, 38.4 mmol) in DMF (40 nL) was treated with a solution of 2-cyanoacrylonitrile (2.30 g, 26.3 mmol) in DMP (40 mL) at room temperature (14 d). The solvent was removed in vacuo and the residue dissolved in dichloromethane and washed with water, brine, and dried (Na2SO4). Concentrated in vacuo, the residue was recrystallized from ethanol to afford 15 as white crystals.
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