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| | 4-chloropyrrolo[1,2-f][1,2,4]triazine Basic information |
| Product Name: | 4-chloropyrrolo[1,2-f][1,2,4]triazine | | Synonyms: | 4-chloropyrrolo[1,2-f][1,2,4]triazine;Pyrrolo[2,1-f][1,2,4]triazine,4-chloro-;4-Chloropyrrolo[1,2-f][1,...;4-chloropyrrolo[1;4-Chloropyrrolo[2,1-f][1,2,4]triazine | | CAS: | 888720-29-4 | | MF: | C6H4ClN3 | | MW: | 153.57 | | EINECS: | | | Product Categories: | CHIRAL CHEMICALS;Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals | | Mol File: | 888720-29-4.mol | ![4-chloropyrrolo[1,2-f][1,2,4]triazine Structure](CAS/GIF/888720-29-4.gif) |
| | 4-chloropyrrolo[1,2-f][1,2,4]triazine Chemical Properties |
| density | 1.51 | | storage temp. | under inert gas (nitrogen or Argon) at 2-8°C | | pka | -2.85±0.30(Predicted) | | Appearance | White to light yellow Solid |
| | 4-chloropyrrolo[1,2-f][1,2,4]triazine Usage And Synthesis |
| Uses | 4-Chloropyrrolo[1,2-f][1,2,4]triazine is a pyrrolotriazine derivative used in the preparation of kinase inhibitors for treating cancer. | | Synthesis | General procedure for the synthesis of 4-chloropyrrolo[1,2-f][1,2,4]triazine from pyrrolo[2,1-f][1,2,4]triazin-4(3H)-one:
Step 3: Synthesis of 4-chloropyrrolo[1,2-f][1,2,4]triazine
Diisopropylethylamine (3.5 mL, 20.3 mmol) was added to a solution of pyrrolo[1,2-f][1,2,4]triazin-4(3H)-one (2.5 g, 18.5 mmol) dissolved in toluene (37.5 mL) under nitrogen protection. Subsequently, phosphorus trichloride (5.1 mL, 55.7 mmol) was added and the reaction mixture was heated at 100 °C for 20 hours. Upon completion of the reaction, the mixture was cooled to 0 °C, aqueous sodium bicarbonate was added slowly and stirred at room temperature for 30 min. The aqueous layer was extracted with ethyl acetate and the organic phase was dried with magnesium sulfate and filtered. The filtrate was concentrated in vacuo to give a yellow solid product which could be used in the next reaction without further purification (2.31 g, 15.0 mmol, 81% yield).
1H NMR (400 MHz, CDCl3) δ: 8.22 (s, 1H), 7.87 (dd, J = 2.4 Hz, 1.6 Hz, 1H), 7.00-6.97 (m, 2H). | | References | [1] Patent: US2011/183983, 2011, A1. Location in patent: Page/Page column 32
[2] Patent: WO2008/86128, 2008, A2. Location in patent: Page/Page column 35
[3] Patent: WO2015/54358, 2015, A1. Location in patent: Page/Page column 106 |
| | 4-chloropyrrolo[1,2-f][1,2,4]triazine Preparation Products And Raw materials |
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