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| | 2-HYDROXY-3-PYRAZINECARBOXYLIC ACID Basic information |
| Product Name: | 2-HYDROXY-3-PYRAZINECARBOXYLIC ACID | | Synonyms: | 3-HYDROXY-PIPERAZINE-2-CARBOXYLIC ACID;3-HYDROXYPYRAZINE-2-CARBOXYLIC ACID;2-HYDROXY-3-PYRAZINECARBOXYLIC ACID;3-Hydroxy-2-pyrazinecarboxylic acid;3-hydroxy-2-pyrazinecarboxylic acid(SALTDATA: FREE);2-Pyrazinecarboxylicacid, 3,4-dihydro-3-oxo;3-Oxo-3,4-dihydropyrazine-2-carboxylic acid;3-Hydroxypyrazinecarboxylic acid | | CAS: | 20737-42-2 | | MF: | C5H4N2O3 | | MW: | 140.1 | | EINECS: | | | Product Categories: | pharmacetical;Piperazine series;Pyrazine | | Mol File: | 20737-42-2.mol |  |
| | 2-HYDROXY-3-PYRAZINECARBOXYLIC ACID Chemical Properties |
| Melting point | 218-220 °C | | density | 1.63±0.1 g/cm3(Predicted) | | storage temp. | 2-8°C | | pka | 12.72±0.20(Predicted) | | Appearance | Light yellow to yellow Solid | | InChI | InChI=1S/C5H4N2O3/c8-4-3(5(9)10)6-1-2-7-4/h1-2H,(H,7,8)(H,9,10) | | InChIKey | FJZRUSFQHBBTCC-UHFFFAOYSA-N | | SMILES | C1(C(O)=O)=NC=CNC1=O | | CAS DataBase Reference | 20737-42-2(CAS DataBase Reference) |
| | 2-HYDROXY-3-PYRAZINECARBOXYLIC ACID Usage And Synthesis |
| Synthesis | Example 4: Synthesis of 3-[3-(5-chloro-1H-benzimidazol-2-yl)-azetidin-1-yl]-pyrazine-2-carboxylic acid
Step 1. Preparation of 3-hydroxypyrazine-2-carboxylic acid: 3-aminopyrazine-2-carboxylic acid (6.95 g, 0.05 mol) was dissolved in a mixed solution of water (55 mL) and sulfuric acid (55 mL, 3.75 M) and heated to 50 °C. Sodium nitrite solution (18.5 mL, 0.06 mol) was slowly added to this solution and the reaction mixture was subsequently cooled to 12 °C. During the addition, the reaction temperature was maintained in the range of 10-16 °C for 30 minutes. Afterwards, the mixture was heated to boiling over 30 minutes. After completion of the reaction, it was cooled to room temperature and filtered to collect the yellow solid. The resulting solid was dissolved in dilute sodium bicarbonate solution, acidified with 10% hydrochloric acid to precipitate the carboxylic acid product and collected by filtration. The crude product was purified by recrystallization from water to give a yellow-orange crystalline solid (4.1 g, 58% yield). | | References | [1] Synthetic Communications, 2010, vol. 40, # 20, p. 2988 - 2999
[2] Patent: WO2011/143129, 2011, A1. Location in patent: Page/Page column 62
[3] Journal of Heterocyclic Chemistry, 1997, vol. 34, # 1, p. 27 - 32
[4] Patent: WO2013/169907, 2013, A1. Location in patent: Page/Page column 44; 45
[5] MedChemComm, 2015, vol. 6, # 7, p. 1311 - 1317 |
| | 2-HYDROXY-3-PYRAZINECARBOXYLIC ACID Preparation Products And Raw materials |
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