[CH:1]([CH:3]1[C:12]2[C:7](=[CH:8][C:9]([C:13]#[N:14])=[CH:10][CH:11]=2)[O:6][CH2:5][CH2:4]1)=O.[N:15]1([CH2:21][CH2:22][C:23]2[CH:32]=[CH:31][C:26]3[C:27](=[O:30])[O:28][CH2:29][C:25]=3[CH:24]=2)[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[O:30]=[C:27]1[C:26]2[CH:31]=[CH:32][C:23]([CH2:22][CH2:21][N:15]3[CH2:20][CH2:19][N:18]([CH2:1][CH:3]4[C:12]5[C:7](=[CH:8][C:9]([C:13]#[N:14])=[CH:10][CH:11]=5)[O:6][CH2:5][CH2:4]4)[CH2:17][CH2:16]3)=[CH:24][C:25]=2[CH2:29][O:28]1To a 12 mL reaction vial was added 4-formyl-3,4-dihydro-2H-chromene-7-carbonitrile (50 mg, 0.27 mmol), 5-[2-(piperazin-1-yl)ethyl]-2-benzofuran-1(3H)-one (66 mg, 0.27 mmol) and dichloromethane (3 mL). The solution was stirred at RT under N2 for 10 min. To above solution was added sodium tris(acetoxy) borohydride (224 mg, 1.1 mmol). The reaction was stirred at RT for 18 hours under N2, extracted with DCM, washed with brine and water. The organic phase was dried over MgSO4, filtered and purified by flash column chromatography. LC-MS (IE, m/z): 418.1 [M+1]+. 1H NMR (500 MHz, CDCl3, δ in ppm): 7.84 (1H, d, J=7.8 Hz), 7.38 (1H, d, J=7.8 Hz), 7.32 (2H, m), 7.11 (1H, dxd, J=8.0 Hz, J=1.6 Hz), 7.08 (1H, d, J=1.6 Hz), 5.60 (2H, s), 4.4 (2H, m), 3.0 (4H, m), 2.4-2.8 (10H, m), 2.0 (2H, m). (0.092 μM)
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