[C:1]([C:4]1[S:5][C:6](Cl)=[CH:7][CH:8]=1)(=O)C.[Cl:10][C:11]1[S:15][C:14]([C:16]([CH2:18][C:19]#[N:20])=[O:17])=[CH:13][CH:12]=1.[CH2:21]([N:28]1CCC(=O)CC1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.N1CCOCC1.[S]>>[NH2:20][C:19]1[S:5][C:4]2[CH2:1][N:28]([CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:6][CH2:7][C:8]=2[C:18]=1[C:16]([C:14]1[S:15][C:11]([Cl:10])=[CH:12][CH:13]=1)=[O:17]The procedure of Example 1 was followed except that 2-acetyl-5-chlorothiophene (Aldrich) was used in place of acetophenone to prepare the corresponding 2-(5-chlorothiophene-2-carbonyl)acetonitrile (Steps A and B). 1-Benzyl-4-piperidone (van der Klein et al., (1999) J. Med. Chem. 42: 3629–3635), 2-(5-chlorothiophene-2-carbonyl)acetonitrile, morpholine, and sulfur were reacted according to the procedure of Step C, Example 1, to afford the desired compound. Yield: 63%; IR (KBr) cm−1: 3306, 2956, 2807, 1715, 1574, 1428, 1354, 1122, 1008, 742, 699; 1H NMR (CDCl3):δ 2.39 (m, 2H), 2.59 (t, 2H, J=5.2 Hz), 3.45 (s, 2H), 3.67 (s, 2H), 6.26 (bs, 2H), 6.87 (d, 1H, J=3.8 Hz), 7.19 (d, 1H, J=4 Hz), 7.35 (m, 5H); yellow solid, mp: 81–83° C. (petroleum ether).
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