Cl[C:2]1[C:7]([C:8]([NH2:10])=[O:9])=[CH:6][N:5]=[C:4]([Cl:11])[CH:3]=1.[S:12]1[CH:16]=[CH:15][CH:14]=[C:13]1[CH2:17][NH2:18].CCN(C(C)C)C(C)C.O>CN1C(=O)CCC1.CCOC(C)=O>[Cl:11][C:4]1[CH:3]=[C:2]([NH:18][CH2:17][C:13]2[S:12][CH:16]=[CH:15][CH:14]=2)[C:7]([C:8]([NH2:10])=[O:9])=[CH:6][N:5]=1A solution of 4,6-dichloronicotinamide (123 mg, 0.643 mmol), thiophen-2-ylmethanamine (0.065 mL, 0.634 mmol) and DIPEA (0.230 mL, 1.32 mmol) in NMP (4 mL) was stirred at 90 C for 18 h. Water and EtOAc were added. The organic phase was separated, dried over Na2SO4, and concentrated in vacuo to give 6-chloro-4-(thiophen-2-ylmethylamino)nicotinamide as a solid (168 mg).
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