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CAS No. : | 147403-65-4 | MDL No. : | MFCD21496678 |
Formula : | C25H24N4O4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 444.48 | Pubchem ID : | - |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-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 |
---|---|---|
90% | With hydroxylamine hydrochloride; sodium hydrogencarbonate In N,N-dimethyl acetamide; water at 70℃; for 18 h; | N, N-dimethylacetamide 2L,Water 16L, added to the reaction bottle,Hydroxylamine hydrochloride (3.37 kg 48.6 mol) was added,Sodium carbonate (5.15 kg 48.6 mol) was added,1-[(2'-cyanobiphenyl-4-yl)methyl]-2-ethoxybenzimidazole-7-carboxylic acid methyl ester(2 kg, 4.86 mol)70 ° C for 18 hours,Cooling, adding water 2L,Precipitation of solid,Filtration was 2-ethoxy-1-[2'-(N'-hydroxycarbamimidoyl)biphenyl-4-yl]-1H-benzimidazole-7-carboxylic acid methyl ester (1.94 g, 37.70 mol),Reference is made to Examples1HPLC conditions Purity: 98.9percent Yield: 90percent. |
85% | With hydroxylamine hydrochloride; sodium hydrogencarbonate In dimethyl sulfoxide at 80 - 85℃; for 20 h; | Dimethyl sulfoxide (75 mL) and hydroxylamine hydrochloride (6 g) were stirred at 20°C to 30°C. Sodium bicarbonate (9 g) was added to the solution and stirred at 45 °C to 50 °C for 1 hour. Methyl-1-[(2'-cyanobiphenyl-4-yl)methyl]-2-ethoxy-1H-benzimidazole-7-carboxylate (3 g) was added to the reaction mixture and heated at 80 °C to 85 °C for 20 hours. The reaction mixture was cooled to 20 °C to 30 °C and de-ionized water (75 mL) was added to the reaction mixture. The solid obtained was filtered and washed with water (75 mL). The solid obtained was purified in 2-butanol (15 mL) at 90 °C to 95 °C for 4 hours and further cooled to 20 °C to 30 °C for 4 hours. The solid obtained was filtered, washed with 2-butanol (6 mL), and dried to obtain the title compound. Yield: 2.75 g (85percent) HPLC Purity: 96.89percent |
70.4% | With hydroxylamine hydrochloride; sodium carbonate In dimethyl sulfoxide at 90℃; | To a 500 mL four-neck flask, 20 g of Compound 1 was added, and while stirring, 100 mL of dimethyl sulfoxide solution in which 10.14 g (3 eq) of hydroxylamine hydrochloride was added was added, and the mixture was heated to 90 DEG C and 30.95 g (6 eq) was added in portions under stirring. Sodium carbonate, after the completion of the reaction for 9-10 hours, after the completion of the reaction, it is allowed to come to room temperature, and 100 mL of water is added to stir the mixture. The solid precipitates, which is cooled down to 0-5°C. Stirring is continued for about 1 hour, and the mixture is dried by suction to obtain 15.2 g of compound 2. The yield was 70.4percent. |
55 g | With hydroxylamine hydrochloride; sodium hydroxide In methanol; N,N-dimethyl acetamide at 10 - 75℃; for 0.5 h; Inert atmosphere | Methanol (400 mL) and sodium hydroxide (56.44 g) were added under a nitrogen atmosphere and stirred at 20° C. to 30° C. to get a clear solution. Dimethylacetamide (750 mL) and hydroxylamine hydrochloride (101.45 g) were added under a nitrogen atmosphere and stirred at 20° C. to 30° C. to get clear solution. Methanolic sodium hydroxide solution was added to the solution of hydroxylamine hydrochloride in dimethylacetamide at 25° C. to 30° C. The reaction mixture was stirred for 30 minutes. Methyl-1-[(2'-cyanobiphenyl-4-yl)methyl]-2-ethoxy-1H-benzimidazole-7-carboxylate (100 g) was added to the reaction mixture at 25° C. to 30° C. and heated to 70° C. to 75° C. for 16 hours to 20 hours. The reaction mixture was cooled to 10° C. to 15° C. The reaction mixture was added to deionized water (1000 mL) at 10° C. to 25° C. The pH of the reaction mixture was adjusted to 0.8 to 1.2 using concentrated hydrochloric acid (150 mL). The reaction mixture was stirred for 30 minutes at 20° C. to 30° C. The reaction mixture was filtered through celite and washed with deionized water (100 mL). The aqueous layer was washed with toluene (500 mL) at 25° C. to 30° C. and the pH of the aqueous layer was adjusted to 8.8 to 9.2 using 30percent solution of sodium carbonate (500 mL) at 20° C. to 30° C. The reaction mixture was stirred for 3 hours to 4 hours at 25° C. to 30° C. The reaction mixture was filtered and washed with deionized water (100 mL) at 20° C. to 30° C. Isobutanol (500 mL) was added to the reaction mixture at 20° C. to 30° C. and the reaction mixture was heated to 90° C. to 95° C. The reaction mixture was stirred for 2 hours at 90° C. to 95° C., cooled to 25° C. to 30° C., and stirred for 4 to 6 hours at 25° C. to 30° C. The reaction mixture was filtered and washed with isobutanol (100 mL) at 20° C. to 30° C. The reaction mixture was dried under vacuum for 30 minutes at 20° C. to 30° C. and then at 45° C. to 50° C. to obtain the title compound. Yield: 55 g |
191.3g | With hydroxylamine hydrochloride; sodium hydrogencarbonate; sodium sulfite In dimethyl sulfoxide at 50 - 85℃; for 12 h; | Taking anhydrous sodium sulfite 122.5 g (0.972 mol)Sodium bicarbonate 408.4 g (4.861 mol)Was added to 2.4 L of DMSO, stirred,A mixture of hydroxylamine hydrochloride (270.2 g, 3.889 mol)Temperature control 50 ~ 55 stirring reaction 2h,Was added 1 - [(2 - cyanobiphenyl-4-yl) methyl] -2-ethoxy-benzimidazole-7-carboxylate (200g, 0.486mol),Temperature control 80 ~ 85 stirring reaction 10h,Rapid dropwise addition of 2.4L water stirring crystallization,Temperature control 20 ~ 25 stirring for 1h,Filtration to give compound II191.3g.HPLC was used to detect compound II 99.07percent and amide impurity 0.32percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71.7% | With hydroxylamine; triethylamine In ethanol; water for 20 h; Reflux | methyl 1-[(2’-cyanobiphenyl-4-yl)methyl] -2-ethoxybenzimidazole-7-carboxylate (0.4 g, 0.97 mmol), 50percent aqueous hydroxylamine solution (1.0 g, 14.5 mmol), Triethylamine (0.1 g, 0.97 mmol) in ethanol (10 ml) was refluxed for 20 h, cooled to crystallize, and filtered to give the title compound (0.31 g, yield 71.7percent).The liquid phase data of the reaction liquid after 20 h showed that the amide impurity: product (liquid chromatographic area ratio): raw material = 7.17: 78.2: 0. |
63% | With hydroxylamine; triethylamine In ethanol; water for 24 h; | Raw material (compound 2A) 20 g, in the reaction bottle, adding ethanol to 200 ml, triethylamine 5 g, 50percent aqueous hydroxylamine solution 37 g, reaction 24h, the cooling crystallization, the white solid obtained 13.6 g (63.0percent). HPLC detection reaction in the reaction solution at the end of the major amide impurity (compound 6A): product is 7.15percent : 92.84percent (that is, the impurity and the product of the ratio of 1 : 12.9), see Figure 2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74.8 %Chromat. | With potassium <i>tert</i>-butylate In 1-methyl-pyrrolidin-2-one at 20℃; for 4 h; | Example 4 Methyl 2-ethoxy- 1 -((2'-(5-oxo-4,5-dihydro- 1 ,2,4-oxadiazol-3 -yl)biphenyl-4-yl)methyl)- 1 H- benzo[ |
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