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| | (2E)-3-(Dimethylamino)-1-(3-pyridyl)prop-2-en-1-one Basic information |
| Product Name: | (2E)-3-(Dimethylamino)-1-(3-pyridyl)prop-2-en-1-one | | Synonyms: | (2E)-3-(DiMethylaMino)-1-(pyridin-3-yl)prop-2-en-1-one;(2E)-3-(DiMethylaMino)-1-(3-pyridyl)prop-2-en-1-one (IMpurity of Nilotinib);(2E)-3-(Dimethylamino)-1-(3-pyridyl)prop-2-en-1-one;Imatinib EP Impurity A (Nilotinib Impurity 16);Nilotinib Impurity 16 (Imatinib EP Impurity A);Imatinib impurity 14/(E)-3-(dimethylamino)-1-(pyridin-3-yl)prop-2-en-1-one;(E)-3-(dimethylamino);Nilotinib IMpurity ((2E)-3-(DiMethylaMino)-1-(3-pyridyl)prop-2-en-1-one) | | CAS: | 123367-26-0 | | MF: | C10H12N2O | | MW: | 176.22 | | EINECS: | | | Product Categories: | | | Mol File: | 123367-26-0.mol |  |
| | (2E)-3-(Dimethylamino)-1-(3-pyridyl)prop-2-en-1-one Chemical Properties |
| Melting point | 113℃ | | Boiling point | 281℃ | | density | 1.070 | | Fp | 124℃ | | storage temp. | under inert gas (nitrogen or Argon) at 2-8°C | | solubility | Acetonitrile (Slightly), Chloroform (Slightly), Methanol (Slightly) | | form | Solid | | pka | 4.74±0.70(Predicted) | | color | Dark Brown to Very Dark Brown | | Major Application | pharmaceutical (small molecule) | | InChI | InChI=1S/C10H12N2O/c1-12(2)7-5-10(13)9-4-3-6-11-8-9/h3-8H,1-2H3/b7-5+ | | InChIKey | MZLRFUCMBQWLNV-FNORWQNLSA-N | | SMILES | C(C1=CC=CN=C1)(=O)/C=C/N(C)C |
| | (2E)-3-(Dimethylamino)-1-(3-pyridyl)prop-2-en-1-one Usage And Synthesis |
| Description | (2E)-3-(Dimethylamino)-1-(3-pyridyl)prop-2-en-1-one is a pharmaceutical intermediate used as an intermediate of nilotinib, a targeted anticancer drug for the treatment of chronic myeloid leukaemia (CML). | | Uses | (2E)-3-(Dimethylamino)-1-(3-pyridyl)prop-2-en-1-one acts as a reagent for the synthesis of oxindole-linked indolyl-pyrimidine derivatives which are potential cytotoxic agents. | | Synthesis | Example-2: Preparation of 3-dimethylamino-1-pyridin-3-ylacrylone
Method A: 3-Acetylpyridine (25 g, 0.20 mol), N,N-dimethylformamide dimethyl acetal (37 g, 0.31 mol) and acetic acid (2.5 ml) were mixed and the reaction was heated at 90-95°C for 2 hours, during which time the methanol produced was continuously removed. After completion of the reaction, excess methanol in the reaction was removed by distillation under reduced pressure. The reaction mixture was diluted with water and extracted with dichloromethane (125 ml). The organic layer was washed with water and the solvent was removed by distillation under reduced pressure to afford 34 g (92% yield) of (E)-3-(dimethylamino)-1-(pyridin-3-yl)prop-2-en-1-one with a purity of 99.1% by HPLC analysis. | | Solubility in organics | (2E)-3-(Dimethylamino)-1-(3-pyridyl)prop-2-en-1-one is soluble in chloroform and dichloromethane. | | References | [1] Synlett, 2016, vol. 27, # 15, p. 2233 - 2236
[2] RSC Advances, 2018, vol. 8, # 47, p. 26828 - 26836
[3] Molecules, 2009, vol. 14, # 10, p. 4166 - 4179
[4] Patent: WO2011/39782, 2011, A1. Location in patent: Page/Page column 14
[5] Organic Process Research and Development, 2008, vol. 12, # 3, p. 490 - 495 |
| | (2E)-3-(Dimethylamino)-1-(3-pyridyl)prop-2-en-1-one Preparation Products And Raw materials |
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