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| | Ethyl 2-chloro-2-(2-(4-methoxyphenyl)hydrazono)acetate Basic information |
| Product Name: | Ethyl 2-chloro-2-(2-(4-methoxyphenyl)hydrazono)acetate | | Synonyms: | 2-chloro-2-[2-(4-methoxyphenyl)hydrazinylidene];ethyl 2-chloro-2-[(4-methoxyphenyl)hydrazinylidene]acetate;Apixaban Impurity B;(Z)-Ethyl 2-chloro-2-(2-(4-methoxyphenyl)hydrazono)acetate
(Apixaban);Apixaban-2;1-(4-methoxyphenyl)-4-(2-((4-(2-oxopiperidin-1-yl)phenyl)amino)ethyl)-1H-pyrazole-3,5-dicarboxamide;Chloro[(4-methoxyphenyl)hydrazono]acetic acid ethyl ester;(Z)- Ethyl chloro[(4-Methoxyphenyl)hydrazono]acetate | | CAS: | 27143-07-3 | | MF: | C11H13ClN2O3 | | MW: | 256.69 | | EINECS: | 608-053-7 | | Product Categories: | 27143-07-3 | | Mol File: | 27143-07-3.mol |  |
| | Ethyl 2-chloro-2-(2-(4-methoxyphenyl)hydrazono)acetate Chemical Properties |
| Melting point | 94℃ | | Boiling point | 349.0±44.0 °C(Predicted) | | density | 1.23 | | storage temp. | 2-8°C | | solubility | Chloroform (Sparingly), Methanol (Slightly) | | form | Solid | | pka | 11.63±0.10(Predicted) | | color | Yellow to Dark Yellow | | InChI | InChI=1S/C11H13ClN2O3/c1-3-17-11(15)10(12)14-13-8-4-6-9(16-2)7-5-8/h4-7,13H,3H2,1-2H3 | | InChIKey | ATNPZEGMKLGIFA-UHFFFAOYSA-N | | SMILES | C(OCC)(=O)C(Cl)=NNC1=CC=C(OC)C=C1 |
| | Ethyl 2-chloro-2-(2-(4-methoxyphenyl)hydrazono)acetate Usage And Synthesis |
| Physical properties | Light yellow to dark yellow solid | | Uses | Acetic acid, 2-chloro-2-[2-(4-methoxyphenyl)hydrazinylidene], ethyl ester is an ester derivative and can be used as an intermediate in the synthesis of apixaban. | | Synthesis | Step-1:Water (600 ml) was added to p-anisidine (100 g) at room temperature and the resulting mixture was cooled to 10°C, followed by the addition of concentrated hydrochloric acid (133.5 g). The resulting mixture was cooled to —5°C to 0°C, followed by portion-wise addition of 40 % aqueous sodium nitrite solution over 45 minutes to 1 hour. The resulting mass was stirred for 1 hour 30 minutes at —5°C to0°C, followed by slow addition of 11 % sulfamic acid solution over 1 hour to 1 hour 30 minutes to produce a reaction mass (first part).Step-2:Sodium acetate (146 g) was added to water (300 ml) at room temperature and then stirred for 10 minutes to 15 minutes, followed by the addition of ethyl 2-chloroacetoacetate (160.4g) and acetone (300 ml) at room temperature to form a reaction mixture. The resulting mixture was cooled to 0°C. The resulting mixture was added to the reaction mass (first part) obtained in step-i at —5°C to 0°C and then stirred for 1 hour at the same temperature. Acetone (200 ml) was added to the resulting mass and stirred for 30 minutes at —5°C to 0°C. The resulting mass was settled for 5 hours at —5°C to 0°Cand then filtered the solid. Methanol (150 ml) was added to the resulting solid at room temperature and then stirred for 2 hours at the same temperature. Ethyl 2-chloro-2-(2-(4-methoxyphenyl) hydrazone)acetate was obtained through further purity. | | References | [1] Patent: CN104513239, 2017, B. Location in patent: Paragraph 0197; 0238; 0243; 0244
[2] European Journal of Medicinal Chemistry, 2016, vol. 123, p. 431 - 446
[3] Patent: CN107400131, 2017, A. Location in patent: Paragraph 0026; 0031; 0042-0044
[4] Patent: CN105384739, 2016, A. Location in patent: Paragraph 0391; 0392; 0393
[5] Patent: CN104395312, 2016, B. Location in patent: Paragraph 0396; 0451-0455; 0501; 0502-0506 |
| | Ethyl 2-chloro-2-(2-(4-methoxyphenyl)hydrazono)acetate Preparation Products And Raw materials |
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