Methyl 2-aminopyridine-4-carboxylate CAS 6937-03-7
Methyl 2-aminopyridine-4-carboxylate Basic information
| Product Name: | Methyl 2-aminopyridine-4-carboxylate |
| Synonyms: | METHYL 2-AMINOISONICOTINATE;METHYL 2-AMINOPYRIDINE-4-CARBOXYLATE;CHEMBRDG-BB 4015127;2-Aminopyridinecarboxylic acid methyl ester~Methyl 2-aminoisonicotinate;2-Aminopyridine-4-carboxylic acid methyl ester;2-aminopyridinecarboxylic acid methyl ester;2-amino-3-methyl-4-pyridinecarboxylate;Methyl 2-aminoisonicotinate 98% |
| CAS: | 6937-03-7 |
| MF: | C7H8N2O2 |
| MW: | 152.15 |
| EINECS: | 627-546-8 |
| Product Categories: | Amines;Heterocycles;Esters;Pyridines;Pyridine;Inhibitors;API intermediates;Heterocycle-Pyridine series |
| Mol File: | 6937-03-7.mol |
Methyl 2-aminopyridine-4-carboxylate Chemical Properties
| Melting point | 144-148 °C |
| Boiling point | 296.1±20.0 °C(Predicted) |
| density | 1.238±0.06 g/cm3(Predicted) |
| storage temp. | Keep in dark place,Sealed in dry,Room Temperature |
| solubility | Chloroform |
| form | Crystalline Powder |
| pka | 4.89±0.11(Predicted) |
| color | White to brown |
| Water Solubility | Insoluble in water. |
| BRN | 128642 |
| InChI | InChI=1S/C7H8N2O2/c1-11-7(10)5-2-3-9-6(8)4-5/h2-4H,1H3,(H2,8,9) |
| InChIKey | SVWWNEYBEFASMP-UHFFFAOYSA-N |
| SMILES | C1(N)=NC=CC(C(OC)=O)=C1 |
| CAS DataBase Reference | 6937-03-7(CAS DataBase Reference) |
Safety Information
| Hazard Codes | Xi |
| Risk Statements | 36/37/38-41-20/22 |
| Safety Statements | 26-36-26/36-39-36/37/39-22 |
| WGK Germany | WGK 2 |
| HazardClass | IRRITANT |
| HS Code | 29333990 |
| Storage Class | 11 - Combustible Solids |
| Hazard Classifications | Eye Dam. 1 |
| Chemical Properties | Tan Solid |
| Uses | Methyl 2-aminopyridine-4-carboxylate is an inhibitor of nitrogen monoxide synthetase. |
| Uses | A nitrogen monoxide synthetase inhibitor. |
| Synthesis Reference(s) | The Journal of Organic Chemistry, 72, p. 4554, 2007 DOI: 10.1021/jo070189y |
| Synthesis | 67-56-1 13362-28-2 6937-03-7 The general procedure for the synthesis of methyl 2-aminoisonicotinate from methanol and 2-aminoisonicotinic acid was as follows: 2-aminoisonicotinic acid (207 g, 1.5 mol) was dissolved in methanol (1.8 L) to prepare a solution. The solution was slowly added dropwise to thionyl chloride (238 g, 2 mol) at 50 °C. After the dropwise addition was completed, the reaction temperature was maintained at 50 °C and the reaction mixture continued to be stirred for 5 hours. After completion of the reaction, the solvent was removed by distillation under reduced pressure. To the residue, saturated aqueous sodium carbonate solution was added and the pH was adjusted to 9-10 to make the reaction mixture basic. Subsequently, the mixed solution was extracted with dichloromethane (300 ml each time for 3 times). The organic layers were combined and dried with anhydrous sodium sulfate. Finally, the solvent was removed by concentration to give methyl 2-aminoisonicotinate (189 g, 83% yield) as a yellow solid. The structure of the product was confirmed by 1H-NMR (d6-DMSO, 300 MHz): δ 3.96 (s, 3H); 7.14 (d, 1H); 7.49 (br, 1H); 8.07 (d, 1H); 8.18 (br, 2H, NH). |
| References | [1] European Journal of Medicinal Chemistry, 2013, vol. 61, p. 26 - 40 [2] Journal of the American Chemical Society, 2018, vol. 140, # 9, p. 3322 - 3330 [3] Chemistry - A European Journal, 2012, vol. 18, # 27, p. 8498 - 8507 [4] Patent: EP3018125, 2016, A1. Location in patent: Paragraph 0515-0518 [5] Russian Journal of Organic Chemistry, 2015, vol. 51, # 5, p. 744 - 745 |
Methyl 2-aminopyridine-4-carboxylate Preparation Products And Raw materials
| Raw materials | Methanol-->Chloroacetaldehyde-->4-Methylpyridin-2-amine-->Methyl 2-amino-5-bromo-4-pyridinecarboxylate-->2-Aminoisonicotinic acid |
| Preparation Products | TERT-BUTYL 4-(AMINOMETHYL)PYRIDIN-2-YLCARBAMATE-->(2-TERT-BUTOXYFORMAMIDO-PYRIDIN-4-YL)METHYL METHANESULFONATE-->TERT-BUTYL 4-(HYDROXYMETHYL)PYRIDIN-2-YLCARBAMATE-->TERT-BUTYL 4-(METHOXYCARBONYL)PYRIDIN-2-YLCARBAMATE-->Methyl 2-aMino-5-chloropyridine-4-carboxylate-->2-(2-Amino-4-pyridyl)-2-propanol-->1-(2-AMINO-PYRIDIN-4-YL)-ETHANONE-->2-PHENYL-IMIDAZO[1,2-A]PYRIDINE-7-CARBOXYLIC ACID METHYL ESTER |
