Reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:13]2[N:12]=[C:11]([C:14](Cl)(Cl)Cl)[NH:10][C:9]=2[CH:8]=[CH:7][CH:6]=1)=[O:4].Cl.Cl.[CH:20]([N:23]1[CH2:28][CH2:27][CH:26]([NH2:29])[CH2:25][CH2:24]1)([CH3:22])[CH3:21].C([O-])(O)=[O:31].[Na+]>C1COCC1.O>[CH3:1][O:2][C:3]([C:5]1[C:13]2[N:12]=[C:11]([C:14](=[O:31])[NH:29][CH:26]3[CH2:27][CH2:28][N:23]([CH:20]([CH3:22])[CH3:21])[CH2:24][CH2:25]3)[NH:10][C:9]=2[CH:8]=[CH:7][CH:6]=1)=[O:4]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of 3.99 g (13.6 mmol) 2-trichloromethyl-1H-benzoimidazole-4-carboxylic acid methyl ester in 40 mL THF was added slowly to a mixture of 2.9 g (13.6 mmol) 1-isopropyl-piperidin-4-ylamine-dihydrochloride and 13.7 g (0.163 mol, 12 equivalents) NaHCO3 in 200 mL THF and 120 mL water. The reaction mixture was stirred for 2 h at RT. The THF was distilled off. The resulting aqueous suspension was diluted with 200 mL CH2Cl2 and extracted twice with 150 mL water. The organic layer was concentrated under reduced pressure and the resulting residue was purified by flash-chromatography on silica gel using an ethyl acetate/methanol-(4:1)-mixture as eluent. The title compound was obtained as a light brown crystalline material.
Workup
- distillationThe THF was distilled off
- additionThe resulting aqueous suspension was diluted with 200 mL CH2Cl2
- extractionextracted twice with 150 mL water
- concentrationThe organic layer was concentrated under reduced pressure
- customthe resulting residue was purified by flash-chromatography on silica gel using an ethyl acetate/methanol-(4
Sources & evidence
- ORD record
- ord-44f8c6df8ba24f0490d82b7e11209947
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07741341B2
Linked notes
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