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| | Methyl 3-amino-6-bromopyrazine-2-carboxylate Basic information |
| Product Name: | Methyl 3-amino-6-bromopyrazine-2-carboxylate | | Synonyms: | METHYL 3-AMINO-6-BROMOPYRAZINE-2-CARBOXYLATE;Methyl 6-Bromo-3-aminopyrazine-2-carboxylic ester;5-AMINO-2-BROMO-6-PYRAZINECARBOXYLIC ACIDMETHYL ESTER;3-Amino-6-bromopyrazine-2-carboxylic acid methyl ester;2-pyrazinecarboxylic Acid, 3-amino-6-bromo-, Methyl Ester;5-amino-2-bromo-6-pyrazinecarboxylicacid methyl es;5-Bromo-3-(methoxycarbonyl)pyrazin-2-amine, 2-Amino-5-bromo-3-(methoxycarbonyl)pyrazine;2-Amino-5-bromo-3-(methoxycarbonyl)pyrazine | | CAS: | 6966-01-4 | | MF: | C6H6BrN3O2 | | MW: | 232.03 | | EINECS: | 687-153-2 | | Product Categories: | Bases & Related Reagents;Heterocycles;Nucleotides | | Mol File: | 6966-01-4.mol |  |
| | Methyl 3-amino-6-bromopyrazine-2-carboxylate Chemical Properties |
| Melting point | 164-166C | | Boiling point | 322.4±37.0 °C(Predicted) | | density | 1.754±0.06 g/cm3(Predicted) | | storage temp. | Keep in dark place,Sealed in dry,Room Temperature | | solubility | soluble in Chloroform, Ethyl Acetate, Methanol | | pka | -1.74±0.10(Predicted) | | form | Solid | | color | Off-white to yellow | | InChI | InChI=1S/C6H6BrN3O2/c1-12-6(11)4-5(8)9-2-3(7)10-4/h2H,1H3,(H2,8,9) | | InChIKey | CNXSIRHOIFRMOB-UHFFFAOYSA-N | | SMILES | C1(C(OC)=O)=NC(Br)=CN=C1N | | CAS DataBase Reference | 6966-01-4 |
| Hazard Codes | Xi | | Risk Statements | 43 | | Safety Statements | 37 | | WGK Germany | WGK 3 | | HS Code | 2933998090 | | Storage Class | 11 - Combustible Solids | | Hazard Classifications | Skin Sens. 1 |
| | Methyl 3-amino-6-bromopyrazine-2-carboxylate Usage And Synthesis |
| Chemical Properties | Orange Solid | | Uses | Pyrazine derivatives as Axl and C-Met receptor enzyme inhibitors. | | Synthesis | General Steps:
Example 1; Synthesis of 3-methyl-6-(4-(methylsulfonyl)phenyl)-N-phenylpiperazine-2-carboxamide (Compound IV-1) Method A:
Step 1: Preparation of methyl 3-amino-6-bromopyrazine-2-carboxylate[A
Methyl 3-aminopyrazine-2-carboxylate (8.35 g, 54.53 mmol) was mixed with N-bromosuccinimide (9.705 g, 54.53 mmol) in acetonitrile (100 mL), and the reaction was stirred for 16 hours at room temperature. After completion of the reaction, the precipitate was collected by filtration, washed with acetonitrile and dried to afford the target product methyl 3-amino-6-bromopyrazine-2-carboxylate as a yellow solid (11.68 g, 92% yield).
1H NMR (400.0 MHz, DMSO-d6) δ 3.85 (s, 3H), 7.55 (br s, 2H), 8.42 (s, 1H) ppm; MS (ES+) m/z 233. | | References | [1] Patent: WO2007/61360, 2007, A2. Location in patent: Page/Page column 71
[2] Heterocycles, 2005, vol. 65, # 10, p. 2321 - 2327
[3] Patent: WO2004/92177, 2004, A1. Location in patent: Page 35-36
[4] Patent: US2011/59118, 2011, A1. Location in patent: Page/Page column 84-85
[5] Patent: WO2010/54398, 2010, A1. Location in patent: Page/Page column 90 |
| | Methyl 3-amino-6-bromopyrazine-2-carboxylate Preparation Products And Raw materials |
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