[CH:1]([C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][C:4]=1[O:11][CH3:12])=O.[CH2:13]([C:15]1[N:16]=[C:17]([CH2:20][C:21]([CH3:23])=[O:22])[S:18][CH:19]=1)[CH3:14].N1CCCCC1.C(O)(=O)C>ClCCl>[CH2:13]([C:15]1[N:16]=[C:17]([C:20]([C:21](=[O:22])[CH3:23])=[CH:1][C:3]2[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][C:4]=2[O:11][CH3:12])[S:18][CH:19]=1)[CH3:14]
770 mg (4.78 mmol) of the compound from example 3A and 890 mg (5.26 mmol) of the compound from example 17A are dissolved in 15 ml of dichloromethane, and 0.473 ml (4.78 mmol) of piperidine and 0.247 ml (4.78 mmol) of acetic acid are added. The reaction mixture is heated under reflux with an inverse water trap overnight. The volatile components are removed in a rotary evaporator, and the crude product is purified by MPLC (Biotage 12M cartridge, eluent: isohexane/ethyl acetate 80:20→70:30). 920 mg (66% of theory) of 4-[2-(4-ethyl-1,3-thiazol-2-yl)-3-oxobut-1-en-1-yl]-3-methoxybenzonitrile are obtained as a mixture of the E/Z isomers {LC-MS (Method 1): Rt=2.39 min; (Elpos): m/z=313 [M+H]+} and without further working up.
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