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Example 188 tert-Butyl N-[5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzoyl]-4-aminobenzoate tert-Butyl 4-aminobenzoate (0.620 g, 6.209 mmol), triethylamine (0.325 g, 3.209 mmol) and <strong>[37091-73-9]2-chloro-1,3-dimethylimidazolinium chloride</strong> (0.542 g, 3.209 mmol) were added to a methylene chloride solution (150 ml) of 5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzoic acid (0.400 g, 1.070 mmol) and the resulting solution was stirred at room temperature for 6 hours. The reaction solution was poured into ice water and then extracted with methylene chloride. The extract was washed with water and then dried, and the solvent was removed by distillation. The obtained residue was purified by preparative thin-layer chromatography (ethyl acetate: hexane = 1:2-->1:0) to obtain the titled compound (0.302 g, 0.549 mmol, 57percent).
Step 1 : iPr2NEt (10 mL) was added into the solution of 2,4,6-trichloro-1,3,5-triazine (2.5 g) and 2,2,2-trifluoroethanol (1.36 g) in THF (100 mL). The reaction was stirred at room temperature for 16 hours before tert-butyl 4-aminobenzoate (2.62 g) was added. The resulting mixture was stirred at room temperature for 40 hours. Then, <strong>[42303-42-4]ethyl <strong>[42303-42-4]1-aminocyclopropanecarboxylate hydrochloride</strong></strong> (2.25 g) was added into the mixture. The reaction was carried out at r.t. for 16 hours, then 115 C. for 16 hours. The reaction was quenched with water. The aqueous layer was extracted with EtOAc (3×100 mL). The combined organic layer was dried over Mg2SO4 and concentrated to offer a residue which will be purified by silica gel chromatography.
Step 1 : iPr2NEt (10 mL) was added into the solution of 2,4,6-trichloro-l,3,5-triazine (2.5 g) and 2,2,2-trifluoroethanol (1.36 g) in THF (100 mL). The reaction was stirred at room temperature for 16 hours before tert-butyl 4-aminobenzoate (2.62 g) was added. The resulting mixture was stirred at room temperature for 40 hours. Then, ethyl 1 -aminocyclopropanecarboxylate hydrochloride (2.25 g) was added into the mixture. The reaction was carried out at r.t. for 16 hours, then 1 15C for 16 hours. The reaction was quenched with water. The aqueous layer was extracted with EtOAc (3 x lOOmL). The combined organic layer was dried over Mg2S04 and concentrated to offer a residue which will be purified by silica gel chromatography.
tert-butyl 4-(3,5-dichloropicolinamido)benzoate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 20℃;
Step 1 : tert-Butyl 4-(3,5-dichloropicolinamido)benzoate N,N-Diisopropylethylamine (5.46 ml, 31.3 mmol) was added to a stirred room temperature mixture of HATU (7.9 g, 20.8 mmol), tert-butyl-4-aminobenzoate 2.4 g (12.5 mmol), and 3,5- dichloropicolinic acid (2 g, 10.4 mmol) in DMF 30 ml. The mixture was stirred at room temperature overnight. The mixture was cooled and diluted with ethyl acetate. The organic phase was washed with aqueous sodium hydrogen carbonate, filtered, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (Biotage 40M), eluting with ethyl acetate/isohexane to give tert-butyl 4-(3,5- dichloropicolinamido)benzoate a yellow solid. MS (ESI) m/z 367.19 (M+H).
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