[C:1]([C:3]1[C:4]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[C:19]([Cl:24])[CH:18]=2)=[C:5]([C:14](O)=[O:15])[S:6][C:7]=1[N:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1)#[N:2].CC[N:27]=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[OH-].[NH4+]>C(Cl)Cl>[C:1]([C:3]1[C:4]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[C:19]([Cl:24])[CH:18]=2)=[C:5]([C:14]([NH2:27])=[O:15])[S:6][C:7]=1[N:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1)#[N:2]To a suspension of 4-cyano-3-(3,4-dichlorophenyl)-5-morpholin-4-ylthiophene-2-carboxylic acid (0.198 g, 0.517 mmol) in DCM (5 mL) was added EDCI (0.198 g, 1.03 mmol) and HOBT (0.140 g, 1.03 mmol). The reaction mixture was stirred at rt for 30 min then ammonium hydroxide (1 mL, 20 mmol) was added. The reaction mixture was stirred for 4 h and was concentrated. The residue was diluted with water and extracted with EtOAc. The organic solutions were combined, washed with sat NaHCO3, with brine, dried over MgSO4, filtered and concentrated to give 4-cyano-3-(3,4-dichlorophenyl)-5-morpholin-4-ylthiophene-2-carboxamide (84) (0.195 g, 99%). LCMS: (FA) ES+ 382.2, ES− 380.1. 1H NMR (300 MHz, d6-DMSO) δ: 7.73 (d, 1H), 7.64 (d, 1H), 7.36 (dd, 1H), 3.73-3.79 (m, 4H) and 3.49-3.54 (m, 4H).
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