N12CCN(CC1)CC2.Cl[C:10]1[C:11]2[S:21][CH:20]=[CH:19][C:12]=2[NH:13][C:14](=[O:18])[C:15]=1[C:16]#[N:17].[N:22]1([C:28]([C:30]2[S:31][CH:32]=[CH:33][CH:34]=2)=[O:29])[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1>CC(N(C)C)=O>[O:18]=[C:14]1[NH:13][C:12]2[CH:19]=[CH:20][S:21][C:11]=2[C:10]([N:25]2[CH2:26][CH2:27][N:22]([C:28]([C:30]3[S:31][CH:32]=[CH:33][CH:34]=3)=[O:29])[CH2:23][CH2:24]2)=[C:15]1[C:16]#[N:17]1,4-Diazabicyclo[2.2.2]octane (3.19 g, 28.48 mmol) was added to a solution of 7-chloro-5-oxo-4,5-dihydro-thieno[3,2-b]pyridine-6-carbonitrile (26) (3.0 g, 14.24 mmol) and piperazin-1-yl-thiophene-2-yl-methanone (3.07 g, 15.60 mmol) in dry DMA. The solution was heated at 110° C. for 1 h. The solution was cooled and poured into ice water. The solids formed were filtered, washed by water, and dried to yield 5-oxo-7-[4-(thiophene-2-carbonyl)-piperazin-1-yl]-4,5-dihydro-thieno[3,2-b]pyridine-6-carbonitrile (4.72 g, 89%) as white solids. MP 293° C.; 1H NMR (400 MHz, DMSO-d6) δ 3.89 (m, 8H), 7.02 (d, J=5.6 Hz, 1H), 7.20 (dd, J=3.6, 5.2 Hz, 1H), 7.54 (dd, J=1.2, 3.6 Hz, 1H), 7.84 (dd, J=1.2, 5.2 Hz, 1H), 8.16 (d, J=5.2 Hz, 1H) ppm; MS m/z=371 amu (M++1).
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