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CAS No. : | 107582-20-7 | MDL No. : | MFCD04038589 |
Formula : | C8H10N2O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | BLJHLOLVEXWHFS-UHFFFAOYSA-N |
M.W : | 166.18 | Pubchem ID : | 571825 |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83.1% | In acetic acid; at 25 - 35℃; for 2 - 3h; | Methyl 2-amino-3-nitrobenzoate (150.0 grams, 0.765 moles) was placed inan autoclave vessel and 1000 mlof ethyl acetate and 75 grams of Raney nickelwere added to the vessel and stirred under a 2-3 kg/cm2 hydrogen pressure for12-15 hours. The catalyst was removed by filtration, and the ethyl acetate wasevaporated under reduced pressure. Acetic acid (170 ml) was added to theresidue, and 180 grams of tetraethylorthocarbonate was slowly added at 25-35°C.The reaction mass was stirred for 2-3 hours, and water (750 ml) was added afterthe reaction mass was cooled to 10°C. The solid was filtered, washed with 150 mlof water, and dried at 50-60°C to get 140 grams (83.1 percent) of methyl 2-ethoxybenzimidazole-7-carboxylate.; 150 grams of 2-Amino-3-nitro-benzoic acid methylester, Raney nickel (75grams), ethyl acetate (1 litre) were charged in an autoclave vessel. 3.0kg/cm2 ofdry hydrogen gas was passed into the reaction suspension for about 20-25 hoursunder agitation. Reaction mass was filtered on celite, followed by washing thecelite with 150 ml of ethyl acetate. Solvent was removed completely from thefiltrate at about 45-50°C by distillation. 171 ml of acetic acid was charged andtetraethylorthocarbonate (180 grams) was added over about 30-45 minutes.Reaction mass was maintained for about 1-3 hours and was cooled to about 0-5°C. 750 ml of water was added over about 15-30 minutes and the separatedsolid was filtered and washed with 150 ml water, followed by 150 ml of ethylacetate. Solid obtained was dried at about 55-65°C for about 10-12 hours to yield140 grams of 2-Ethoxy-3H-benzoimidazole-4-carboxylic acid methylestercompound of Formula (IV). |
With acetic acid; at 25 - 30℃; | (1) Add 120 g of AM5 and 300 ml of glacial acetic acid to the reaction flask.The original tetraethyl carbonate 185g.(2) The reaction is warmed up to 25 to 30°C for 2 to 3 hours. The reaction conditions of the raw materials are observed by spotting until the basic reaction of the raw materials is complete.(3) After the reaction, the water is slowly cooled to 5-10 DEG C and stirred for 2 hours. The mixture is suction filtered, and the solid is washed with water twice and dried to obtain methyl 2-ethoxybenzimidazole-7-carboxylate as a product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 20℃; | A mixture of 5-bromo-lEta-pyrazolo[3,4-b]pyridine-3-carboxylic acid Compound Ic (0.3 g, 1.17 mmol), 2,3-diamino-benzoic acid methyl ester Compound 8a (3.43 g, 20.64 mmol), HATU (7.85 g, 20.66 mmol), DIPEA (8.64 mL, 62 mmol) in DMF (250 mL) was stirred at room temperature overnight. The solvent was removed and the residue was purified by silica gel chromatography (10% to 90% of ethyl acetate in hexanes) to yield 2-amino-3-[(5-bromo-lH-pyrazolo[3,4-b]pyridine-3-carbonyl)- amino] -benzoic acid methyl ester Compound 8b (5.1 g, 63% yield) as a colorless gel. 1H NMR (300 MHz, CD3OD) delta 9.03 (d, IH, J = 2.1 Hz), 8.78 (d, IH, J = 2.1 Hz), 7.58 (d, IH, 7= 7.8 Hz), 7.26 (d, IH, 7= 7.8 Hz), 7.15 (t, IH, 7 = 7.8 Hz), 3.49 (s, 3H); MS (ESI) m/z: 391 (M+H+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine; In dichloromethane; at 0℃; for 1h; | Example 187 [0618] 2,3-diaminobenzoate (100 mg, 0.602 mmol) in dichloromethane (5.00 mL) and TEA (0.252 mL, 1.81 mmol) was treated at 0 C. with <strong>[42926-52-3]2-ethoxybenzoyl chloride</strong> (111 mg, 0.602 mmol). The reaction mixture was stirred at 0 C. for 1 h. The reaction mixture was concentrated in vacuo and the crude material was used directly in the next reaction. |
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