(3-Chloro-benzofuran-2-ylmethyl)methylamine → (E)-N-(3-Chloro-benzofuran-2-ylmethyl)-N-methyl-3-(2-oxo-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl)-acrylamide hydrochloride
Reaction equation
Cl.[O:2]=[C:3]1[NH:9][C:8]2[N:10]=[CH:11][C:12]([CH:14]=[CH:15][C:16]([OH:18])=O)=[CH:13][C:7]=2[CH2:6][NH:5][CH2:4]1.[Cl:19][C:20]1[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=2[O:22][C:21]=1[CH2:29][NH:30][CH3:31]>>[ClH:19].[Cl:19][C:20]1[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=2[O:22][C:21]=1[CH2:29][N:30]([CH3:31])[C:16](=[O:18])/[CH:15]=[CH:14]/[C:12]1[CH:11]=[N:10][C:8]2[NH:9][C:3](=[O:2])[CH2:4][NH:5][CH2:6][C:7]=2[CH:13]=1Participants
3
Reactant 2
Product 1
Procedure
According to the method of example 43d, 3-(2-oxo-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl)-acrylic acid hydrochloride (152 mg, 0.5 mmol) and (3-chloro-benzofuran-2-ylmethyl)methylamine (108 mg, 0.55 mmol) were coupled to yield crude product which was triturated with methanol and ether several times and dried. The residue was re-solvated in methylene chloride (5 mL) and a solution of 2M HCl in ether (2 mL) was added to precipitate the hydrogen chloride salt. The precipitate was collected by filtration and dried to give the title compound (42 mg, 19%) as a white solid and as a mixture of amide rotomers. 1H NMR (400 MHz, DMSO-d6) δ 10.06 (s, 1H), 8.45 (s, 1H), 8.01 (s, 1H), 7.38-7.68 (m, 6H), 4.88-5.08 (rotamers, 2s, 2H), 3.90 (s, 2H), 3.63 (s, 2H), 3.31 (s, 3H); MS (ESI) m/e 411 (C21H19ClN4O3+H)+.