Hydrochloric Acid → (E)-5-Fluoro-(4-methoxystyryl)-1-(2-pyridyl)-1H-benzimidazole hydrochloride
Reaction equation
[F:1][C:2]1[CH:14]=[CH:13][C:5]([NH:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=2)=[C:4]([NH2:15])[CH:3]=1.[CH3:16][O:17][C:18]1[CH:28]=[CH:27][C:21](/[CH:22]=[CH:23]/[C:24]([Cl:26])=O)=[CH:20][CH:19]=1.N1C=CC=CC=1N1C2C=CC=CC=2N=C1/C=C/C1C=CC=CC=1.Cl>CO>[ClH:26].[F:1][C:2]1[CH:14]=[CH:13][C:5]2[N:6]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=3)[C:24](/[CH:23]=[CH:22]/[C:21]3[CH:20]=[CH:19][C:18]([O:17][CH3:16])=[CH:28][CH:27]=3)=[N:15][C:4]=2[CH:3]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
Free base of the titled compound was prepared from 4-fluoro-2-amino-N-(2-pyridyl)aniline and (E)-4-methoxycinnamoyl chloride according to the preparation of (E)-1-(2-pyridyl)-2-styryl-1H-benzimidazole (Example 1, method A). The free base was treated with a 10% methanol solution of hydrogen chloride and concentrated to dryness. The residue was recrystallized from ethyl acetate/ethanol to give the titled compound. MW: 381.84; mp: 204.0-206.0° C.; 1H-NMR (CDCl3) δ: 9.01 (1H, d, J=16.1 Hz), 8.86 (1H, dd, J=4.8, 2.0 Hz), 8.18 (1H, ddd, J=7.7, 7.7, 2.0 Hz), 7.83 (1H, dd, J=7.9, 2.3 Hz), 7.76 (1H, d, J=7.9 Hz), 7.69 (1H, dd, J=7.4, 4.8 Hz), 7.59 (2H, d J=8.7 Hz), 7.40 (1H, dd, J=9.0, 4.2 Hz), 7.17 (1H, ddd, J=9.0, 9.0, 2.3 Hz), 6.85 (2H, d, J=8.7 Hz), 6.78 (1H, d, J=16.1 Hz), 3.82 (3H, s).
Workup
- concentrationconcentrated to dryness
- customThe residue was recrystallized from ethyl acetate/ethanol
Sources & evidence
- ORD record
- ord-89e9af7c3b2242d7bd751c7e2e4bc628
- Source dataset
- uspto-grants-2004_03
- Patent number
- US06713482B2
Reaction notes
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