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Keywords = 3-methyl-6-nitro-1H-indazole

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10 pages, 3901 KiB  
Communication
An Alternative Method for Synthesizing N,2,3-Trimethyl-2H-indazol-6-amine as a Key Component in the Preparation of Pazopanib
by Thi Thanh Cham Bui, Hue Linh Luu, Thi Thanh Luong, Thi Ngoc Nguyen, Nguyet Suong Huyen Dao, Van Giang Nguyen, Dinh Luyen Nguyen, Nguyen Trieu Trinh and Van Hai Nguyen
Chemistry 2024, 6(5), 1089-1098; https://doi.org/10.3390/chemistry6050063 - 19 Sep 2024
Viewed by 1910
Abstract
Due to its application as an anti-cancer drug, pazopanib (1) has attracted the interest of many researchers, and several studies on pazopanib synthesis have been reported over the years. This paper provides a novel route for synthesizing N,2,3-trimethyl-2H-indazol-6-amine [...] Read more.
Due to its application as an anti-cancer drug, pazopanib (1) has attracted the interest of many researchers, and several studies on pazopanib synthesis have been reported over the years. This paper provides a novel route for synthesizing N,2,3-trimethyl-2H-indazol-6-amine (5), which is a crucial building block in the synthesis of pazopanib from 3-methyl-6-nitro-1H-indazole (6). By alternating between the reduction and two methylation steps, compound 5 was obtained in a yield comparable (55%) to what has been reported (54%). It is noteworthy that the last step of N2-methylation also yielded N,N,2,3-tetramethyl-2H-indazol-6-amine (5′) as a novel compound. Furthermore, the data presented in this paper can serve as a valuable resource for future research aimed at further refining the process of synthesizing pazopanib and its derivatives. Full article
(This article belongs to the Section Medicinal Chemistry)
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13 pages, 1578 KiB  
Article
Dimethyloxonium and Methoxy Derivatives of nido-Carborane and Metal Complexes Thereof
by Marina Yu. Stogniy, Svetlana A. Erokhina, Irina D. Kosenko, Andrey A. Semioshkin and Igor B. Sivaev
Inorganics 2019, 7(4), 46; https://doi.org/10.3390/inorganics7040046 - 27 Mar 2019
Cited by 13 | Viewed by 3905
Abstract
9-Dimethyloxonium, 10-dimethyloxonium, 9-methoxy and 10-methoxy derivatives of nido-carborane (9-Me2O-7,8-C2B9H11, 10-Me2O-7,8-C2B9H11, [9-MeO-7,8-C2B9H11]−, and [10-MeO-7,8-C2B9H11 [...] Read more.
9-Dimethyloxonium, 10-dimethyloxonium, 9-methoxy and 10-methoxy derivatives of nido-carborane (9-Me2O-7,8-C2B9H11, 10-Me2O-7,8-C2B9H11, [9-MeO-7,8-C2B9H11]−, and [10-MeO-7,8-C2B9H11]−, respectively) were prepared by the reaction of the parent nido-carborane [7,8-C2B9H12]− with mercury(II) chloride in a mixture of benzene and dimethoxymethane. Reactions of the 9 and 10-dimethyloxonium derivatives with triethylamine, pyridine, and 3-methyl-6-nitro-1H-indazole result in their N-methylation with the formation of the corresponding salts with 9 and 10-methoxy-nido-carborane anions. The reaction of the symmetrical methoxy derivative [10-MeO-7,8-C2B9H11]− with anhydrous FeCl2 in tetrahydrofuran in the presence of t-BuOK results in the corresponding paramagnetic iron bis(dicarbollide) complex [8,8′-(MeO)2-3,3′-Fe(1,2-C2B9H10)2]−, whereas the similar reactions of the asymmetrical methoxy derivative [9-MeO-7,8-C2B9H11]− with FeCl2 and CoCl2 presumably produce the 4,7′-isomers [4,7′-(MeO)2-3,3′-M(1,2-C2B9H10)2]− (M = Fe, Co) rather than a mixture of rac-4,7′- and meso-4,4′-isomers. Full article
(This article belongs to the Special Issue Metal Complexes Containing Boron Based Ligands)
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