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CAS No. : | 95-23-8 | MDL No. : | MFCD00053555 |
Formula : | C7H7N3O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | BCXSVFBDMPSKPT-UHFFFAOYSA-N |
M.W : | 149.15 | Pubchem ID : | 66765 |
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 |
---|---|---|
45.7% | With benzotriazol-1-ol; diisopropyl-carbodiimide; In DMF (N,N-dimethyl-formamide); at 20℃; for 16h; | D) 3, 4-Dibenzyloxy-(5-N-2-oxo-2, 3-dihydro-1H-benzoimidazolyl) benzamide.; 1,3- N, N-Diisopropylcarbodiimde (0.945 g; 7.5 mmol) was added to a solution of 3,4-dibenzyloxy benzoic acid (1.67 g, 5 mmol), 5-amino-2, 3-dihydro-lH- benzoimidazol-5-one (0.745 g, 5 mmol) and 1-hydroxybenzotriazole (0.675 g, 5 mmol) in anhydrous N, N - dimethylformamide (20 ml). After stirring for 16 hrs at room temperature the reaction mixture was poured in water (100 ml). The pH of the mixture was adjusted to 2 with IN hydrochloric acid and stirred for 30 minutes. Filtration and washing the product with ethyl acetate (3 x 10 ml) provided 1.06 grams of 3,4-dibenzyloxy-(5-N-2-oxo-2, 3-dihydro-1H-benzoimidazolyl) benzamide. (Yield = 45.7percent). 1H NMR (CD3)2SO 9.94 (1H, s) 7.65 - 7.2 (14H, m) 7.09 (2H, d, J 8Hz) 5.1 (4H, s) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1% | To a solution of compound 10f (834 mg, 4.4 mmol) and compound9 (550 mg, 3.7 mmol) in DMSO (5 mL) was added DIPEA(1.3 mL, 7.4 mmol) at rt. The mixture was stirred at 100 C for 1d and heated under microwave irradiation at 160 C for 2 h. Thereaction mixture was cooled to rt, diluted with EtOAc and water,and extracted with EtOAc. The extract was washed with waterand brine, dried over Na2SO4, and then evaporated. The residualsolid was suspended in EtOAc and insoluble materials wereremoved by filtration. The filtrate was purified by silica gel columnchromatography (EtOAc:MeOH = 10:0 to 9:1). The fractions werecombined and evaporated. The residual solid was suspended inEtOAc, collected by filtration, washed with EtOAc, and dried to givecompound 1f (17 mg, 0.05 mmol, 1%) as an off-white solid. 1HNMR(DMSO-d6) d 3.78 (3H, s), 6.80-6.95 (4H, m), 7.66 (1H, dd, J = 8.7,2.0 Hz), 7.85 (1H, d, J = 2.0 Hz), 8.03 (1H, s), 10.61 (1H, brs), 10.62(1H, brs). MS m/z 318 (M+H)+. Mp 304-306 C. Anal. Calcd for C15-H12ClN3O30.3H2O: C, 55.75; H, 3.93; N, 13.00. Found: C, 55.93; H,3.86; N, 12.75. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With N-ethyl-N,N-diisopropylamine; In 1-methyl-pyrrolidin-2-one; at 120℃; | A stirred solution of <strong>[475216-25-2]4-fluoro-N-methyl-3-nitrobenzamide</strong>46 (200 mg), 5-amino-lH- benzo[d]imidazol-2(3H)-one50 (151 mg) and N,N-diisopropylethylamine (264 mu) in N-methyl-2- pyrrolidinone (1 ml) was heated at 120 C overnight. The reaction mixture was then cooled to room temperature and the crude product was collected by filtration, washed with water, and then dried in vacuo at 40 C to afford N-methyl-3-nitro-4-((2-oxo-2,3-dihydro-lH-benzo[d]imidazol- 5-yl)amino)benzamide (296 mg, 90%) as a red solid which was used in the next step without further purification. MS (ISP): 328.0 ([M+H]+). |