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| | 5-methyl-2-(2H-1,2,3-triazol-2-yl)benzoic acid Basic information |
| Product Name: | 5-methyl-2-(2H-1,2,3-triazol-2-yl)benzoic acid | | Synonyms: | 2-(2H-1,2,3-TRIAZOL-2-YL)-5-METHYLBENZOIC ACID;5-Methyl-2-(2H-1,2,3-triazol-2-yl)benzoic acid;5-Methyl-2-(2H-1,2,3-triazol-2-yl)benzoic acid (For suvorexant);Suvorexant Intermediate II;5-Methyl-2-(2H-1,2,3-triazol-2-yl)benzoic Acid;Benzoic acid, 5-methyl-2-(2H-1,2,3-triazol-2-yl)-;5-methyl-2-(triazol-2-yl)benzoic acid;Suvorexant: 5-Methyl-2-(2H-1,2,3-triazol-2-yl)benzoic acid | | CAS: | 956317-36-5 | | MF: | C10H9N3O2 | | MW: | 203.2 | | EINECS: | 689-732-5 | | Product Categories: | | | Mol File: | 956317-36-5.mol |  |
| | 5-methyl-2-(2H-1,2,3-triazol-2-yl)benzoic acid Chemical Properties |
| Melting point | 174-176℃ | | Boiling point | 413℃ | | density | 1.35 | | vapor pressure | 0-0.001Pa at 20-70℃ | | Fp | 204℃ | | storage temp. | Sealed in dry,Room Temperature | | solubility | soluble in Methanol | | pka | 3.00±0.36(Predicted) | | form | Solid:particulate/powder | | color | White to Light yellow | | InChI | InChI=1S/C10H9N3O2/c1-7-2-3-9(8(6-7)10(14)15)13-11-4-5-12-13/h2-6H,1H3,(H,14,15) | | InChIKey | SRBAGFIYKNQXDV-UHFFFAOYSA-N | | SMILES | C(O)(=O)C1=CC(C)=CC=C1N1N=CC=N1 | | LogP | 0.3 | | Surface tension | 56.7mN/m at 1.552g/L and 21.7℃ |
| | 5-methyl-2-(2H-1,2,3-triazol-2-yl)benzoic acid Usage And Synthesis |
| Uses | 5-methyl-2-(2H-1,2,3-triazol-2-yl)benzoic acid is mainly used as an intermediate in organic synthesis and medicinal chemistry. It is used in the synthesis of Suvorexant, an orexin antagonist drug used in the treatment of insomnia. | | Synthesis | Step 1) Synthesis of 5-methyl-2-(2H-1,2,3-triazol-2-yl)benzoic acid: under nitrogen protection, N,N-dimethylformamide (30 mL), 1,2,3-triazole (3.45 g, 50 mmol), 2-iodo-5-methylbenzoic acid (5.24 g, 20 mmol), caesium carbonate (11.72 g, 36 mmol), trans-N,N'-dimethyl-1,2-cyclohexanediamine (0.51 g, 3.6 mmol) and cuprous iodide (0.38 g, 2 mmol). The reaction mixture was heated to 100 °C for 4 hours. After completion of the reaction, the mixture was cooled to room temperature, diluted with water (60 mL) and extracted with ethyl acetate (200 mL x 2). The aqueous layer was acidified to pH 1 to 2 with concentrated hydrochloric acid and extracted again with ethyl acetate (200 mL x 2). The organic layers were combined, dried with anhydrous sodium sulfate and filtered. The filtrate was concentrated under vacuum and the residue was purified by silica gel column chromatography (dichloromethane/methanol, v/v=50/1) to give the title compound as a yellow solid (2.76 g, 68%). Mass spectrum (ESI, negative ion) m/z: 202.1 [M-H]-; 1H NMR (CD3OD, 600 MHz) δ (ppm): 7.88 (s, 2H), 7.66 (d, 1H), 7.59 (d, J=8.2 Hz, 1H), 7.50-7.48 (dd, J=8.1 Hz, 1.1 Hz, 1H), 2.45 ( s, 3H); 13C NMR (CD3OD, 151MHz) δ (ppm): 169.8, 140.7, 137.5, 136.7, 133.5, 131.5, 129.3, 126.0, 21.0. | | References | [1] Patent: CN106243052, 2016, A. Location in patent: Paragraph 0238; 0239; 0240; 0241; 0242
[2] Patent: WO2017/88759, 2017, A1. Location in patent: Paragraph 00182
[3] Patent: CN107759620, 2018, A. Location in patent: Paragraph 0183-0187
[4] Patent: WO2010/48014, 2010, A1. Location in patent: Page/Page column 33-34
[5] Patent: WO2010/48017, 2010, A1. Location in patent: Page/Page column 38 |
| | 5-methyl-2-(2H-1,2,3-triazol-2-yl)benzoic acid Preparation Products And Raw materials |
| Raw materials | 2H-1,2,3-Triazole, 2-(4-methylphenyl)--->2-IODO-5-METHYLBENZOIC ACID-->N,N-Dimethylformamide-->Copper(l) iodide-->2-BROMO-5-METHYLBENZOIC ACID-->Cesium carbonate-->5-Methyl-2-(1H-1,2,3-triazol-1-yl)benzoic acid-->Trans-(1R,2R)N,N'-Dimethyl-cyclohexane-1,2-diamine-->Methyl 2-iodo-5-methylbenzoate-->1,2,3-1H-Triazole | | Preparation Products | Suvorexant |
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