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CAS No. : | 956317-36-5 | MDL No. : | MFCD18382679 |
Formula : | C10H9N3O2 | Boiling Point : | No data available |
Linear Structure Formula : | - | InChI Key : | SRBAGFIYKNQXDV-UHFFFAOYSA-N |
M.W : | 203.20 | Pubchem ID : | 53260165 |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | |
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 |
---|---|---|
With copper(l) iodide; (1S,2S)-N,N'-dimethyl-1,2-diaminocyclohexane; caesium carbonate; In N,N-dimethyl-formamide; at 120℃; for 1h;Microwave irradiation; | 5-methyl-2-(2H- 1 .2.3-triazol-2-ylbenzoic acid and 5-methyl-2-( 1 H-i .2,3 -triazol- 1-ylbenzoic acid The mixture of <strong>[6967-82-4]2-bromo-5-methylbenzoic acid</strong> (1 g, 4.65 mmol), 1,2,3-triazole (0.58 g, 8.37 mmol), (1S,2S)-N1,N2-dimethylcyclohexane-1,2-diamine (0.265 g, 1.86 mmol), Cs2CO3 (3.0 g, 9.3 mmol) and CuT (0.089 g, 0.465 mmol) in DMF (15 mL) was degassed and heated at 120 C for lh in a microwave reactor. The reaction was cooled to RT, diluted with MeOH,and acidified with AcOH to pH45. The solvent was removed in vacuo to obtain the crude which was purified by silica gel chromatography (O 100% DCM/EtOAc) to obtain the faster eluting acid 5-methyl-2-(2H-1,2,3-triazol-2-yl)benzoic acid as the major product and the second eluting 5-methyl-2-(1H-1,2,3-triazol-1-yl)benzoic acid as the minor product. ESI-MS (mlz): 204, [M+1]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
500 mg | With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In dichloromethane; at 20℃; | A mixture of compound 6g (300 mg, 1.3 mmol),compound 12 (300 mg, 1.4 mmol), HATU (988 mg, 2.6 mmol) and TEA (260 mg, 2.6mmol) in DCM (30 mL) was stirred at r.t. for overnight. The reaction mixture wasdiluted with water and extracted with EtOAc. The organic layers was concentrated and purified by silica gel chromatography (eluting with petroleumether/EtOAc=20:1~3:1) to give compound 6h (500 mg, yield: 93.6%). MS (ESI): m/z412.1 [M+H]+ |
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