Acetic Acid → Methyl 1-[(2'-cyano[1,1'-biphenyl]-4-yl)methyl]-2-ethoxy-1H-benzimidazole-7-carboxylate
Reaction equation
C(O)(=O)C.[NH2:5][C:6]1[C:7]([NH:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[C:30]#[N:31])=[CH:20][CH:19]=2)=[C:8]([CH:13]=[CH:14][CH:15]=1)[C:9]([O:11][CH3:12])=[O:10].[C:32]([O-])([O-])([O-])[O:33][CH2:34][CH3:35]>>[C:30]([C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=1[C:21]1[CH:22]=[CH:23][C:18]([CH2:17][N:16]2[C:7]3[C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:13][CH:14]=[CH:15][C:6]=3[N:5]=[C:32]2[O:33][CH2:34][CH3:35])=[CH:19][CH:20]=1)#[N:31]Participants
4
Conditions
- Temperature
- 80 °C
Procedure
Acetic acid (0.37 g) was added to a solution of methyl 3-amino-2-[[(2′-cyanobiphenyl-4-yl)methyl]amino]benzoate (2.03 g) in ethyl orthocarbonate (5 ml), and the mixture was stirred at 80° C. for one hour. The reaction mixture was concentrated to dryness and the residue was dissolved in ethyl acetate. The solution was washed with an aqueous solution of sodium hydrogen carbonate and water. The solvent was evaporated in vacuo to give crystals. Recrystallization from ethyl acetate-hexane afforded colorless crystals (2.01 g, 86%), m.p. 168.5-169.5° C.
Workup
- concentrationThe reaction mixture was concentrated to dryness
- dissolutionthe residue was dissolved in ethyl acetate
- washThe solution was washed with an aqueous solution of sodium hydrogen carbonate and water
- customThe solvent was evaporated in vacuo
- customto give crystals
- customRecrystallization from ethyl acetate-hexane afforded colorless crystals (2.01 g, 86%), m.p. 168.5-169.5° C.
Sources & evidence
- ORD record
- ord-d128572dfe754bd6941a945d8dc28289
- Source dataset
- uspto-grants-2003_08
- Patent number
- US06608210B2
Reaction notes
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