Cl.CCO.[Cl:5][C:6]1[CH:13]=[C:12]([C:14]2[N:18](C3CCCCO3)[N:17]=[CH:16][CH:15]=2)[CH:11]=[CH:10][C:7]=1[C:8]#[N:9]>>[ClH:5].[Cl:5][C:6]1[CH:13]=[C:12]([C:14]2[CH:15]=[CH:16][NH:17][N:18]=2)[CH:11]=[CH:10][C:7]=1[C:8]#[N:9]HCl/EtOH ˜10% (35.1 ml, 115 mmol) was set into the reaction flask under nitrogen atmosphere. 2-Chloro-4-(1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-5-yl)-benzonitrile (12 g, 46.2 mmol) was added. The mixture was cooled to 10° C. and agitated for 2 h. Temperature was set to 0° C. and the mixture was stirred additional 2 hours. The precipitation was filtered, washed with ethanol and dried under vacuum overnight to obtain 9.24 g of the title compound. 1H-NMR (400 MHz, DMSO-d6): δ 6.99 (d, 3H), 7.86 (d, 1H), 7.96-8.02 (m, 2H), 8.14-8.17 (m, 1H).
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