Category: 37441-50-2

A common heterocyclic compound, 37441-50-2,1,2-Thiazinane 1,1-dioxide, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route. 37441-50-2

A flask was charged under nitrogen with 1,1-dimethylethyl 3-bromo-5-iodobenzoate (D7)(1 g, 2.6 mmol, 1 equiv), Cs2CO3 (1.26 g, 3.9 mmol, 1.5 equiv),tris(dibenzylideneacetone)dipalladium(0) (12 mg, 0.013 mmol, 0.005 equiv), Xantphos (22 mg, 0.038 mmol, 0.015 equiv) and toluene (20 ml). Tetrahydro-2H-1,2-thiazine 1,1-dioxide (D6) (350 mg, 2.9 mmol, 1.1 equiv) was then added and the resulting mixturewas stirred at 100C for 16 h then cooled to room temperature and diluted with AcOEt.The organic phase was washed with saturated aqueous NaHCO3 solution, dried overMgSO4 and concentrated in vacua. The residue was triturated with Et2O to give 1,1-dimethylethyl 3-bromo-5-(1,1-dioxidotetrahydro-2/-/-1,2-thiazin-2-yl)benzoate (D8) (590mg, 58%) as a white solid., 37441-50-2

This compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,37441-50-2,1,2-Thiazinane 1,1-dioxide,its application will become more common.

Reference£º
Patent; GLAXO GROUP LIMITED; WO2004/111022; (2004); A1;,
Thiazine – an overview | ScienceDirect Topics
Thiazine | C4H5NS – PubChem

The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a downstream synthesis route of the compound 37441-50-2,37441-50-2

solution of 2-(3-chloro-4-fluorobenzyl)-8-ethyl-4-fluoro-10-methoxy-6-methyl-7,8- dihydropyrazino[l’,2′: 1,5]pyrrolo[2,3-d]pyridazine-1,9(2H,6H)-dione (0.10 g, 0.23 mmol; Example 139), 1,2-thiazinane 1,1-dioxide (45 mg, 0.33 mmol), and cesium carbonate (0.15 g, 0.46 mmol) in anhydrous DMSO (9.5 mL) was heated in an oil bath at 50 C for 5 hours. The product mixture was filtered through a pad of Celite and the filtrate was subjected to purification on reverse phase preparative HPLC purification. Collection and lyophilization of appropriate fractions afforded the title material. Analytical HPLC indicated that the product is a 1:1 mixture of two isomers that arose from the relative stereochemistry of the 6-methyl group and restricted rotation between the sultam ring and the tricyclic core. ?H NMR (400 MHz, CDCI3) No. 7.48 (m 1H), 7.28 (m, 1H), 7.11 (t, J = 8.5 Hz, 1H), 5.17 (d, J = 14.2 Hz, ?H), 5.34 (in, 1/2 H), 5.29 (d, J = 14.2 Hz, (at)H), 5.23 (d, J = 14.2 Hz, ?H), 5.09 (d, J = 14.2 Hz, ?H), 5.07 (m, ?H), 4.18 (s, 1.5H), 4.16 (s, 1.5H), 4.12-3.17 (m), 2.58-2.00 (m), 1.57 (d, J = 6.6 Hz, 1.5H), 1.42 (d, J = 6.8 Hz, 1.5H), 1.23 (t, J = 6.8 Hz, 1.5H), 1.22 (t, J = 7.1 Hz, 1.5H). ES MS M+1 = 552, 37441-50-2

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 37441-50-2.

Reference£º
Patent; MERCK & CO., INC.; WO2005/110414; (2005); A2;,
Thiazine – an overview | ScienceDirect Topics
Thiazine | C4H5NS – PubChem

In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 37441-50-2,1,2-Thiazinane 1,1-dioxide, as follows.37441-50-2

Step2 A strong glass tube was charged with Pd2(dba)3 (6.4 mg; 0.007 mmol), xantphos (12 mg; 0.02 mmol), 1,2-thiazinane-1,1-dioxide (115 mg; 0.85 mmol), and Cs2CO3 (323 mg; 0.99 mmol).The tube was capped with a rubber septum, evacuated and backfilled with nitrogen. 6-Bromo-1-methyl-1H-indole carboxylic acid ethyl ester (200 mg; 0.71 mmol) in 1 ml of 1,4-dioxane was added through the septum.The septum was replaced with a Teflon screwcap.The tube was sealed, and the mixture was stirred at 100 C. for 64 hours.The reaction mixture was cooled to room temperature, diluted with ethyl acetate (10 ml), filtered, and concentrated in vacuo.The crude material was purified by flash chromatography (silica gel, ethyl acetate-hexane 1:1) to afford 190 mg (66%; m/z 337) of colorless crystals.This compound was dissolved in a mixture of tetrahydrofuran (4 ml), methanol (2 ml) and water (1 ml).To this solution was added dropwise LiOH monohydrate (95 mg; 2.26 mmol) dissolved in 1 ml water and the mixture was stirred at room temperature for 16 h.The reaction mixture was partition between ethyl acetate and water.The aqueous layer was acidified with 2N HCl to ph ~3-4 and extracted with ethyl acetate.The organic layer was washed with brine and dried (Na2SO4) and evaporated in vacuo.Yield 131 mg of 6-(1,1-Dioxo-1lambda6-[1,2]thiazinan-2-yl)-1-methyl-1H-indole-2-carboxylic acid as a white powder (75%); m/z 307., 37441-50-2

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,2-Thiazinane 1,1-dioxide, and friends who are interested can also refer to it.

Reference£º
Patent; Bamberg, Joe Timothy; Gabriel, Tobias; Krauss, Nancy Elisabeth; Mirzadegan, Taraneh; Palmer, Wylie Solang; Smith, David Bernard; US2004/77646; (2004); A1;,
Thiazine – an overview | ScienceDirect Topics
Thiazine | C4H5NS – PubChem

In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 37441-50-2,1,2-Thiazinane 1,1-dioxide, as follows.37441-50-2

Part E 7-Bromo-2-ethoxymethyl-1-(3-isopropoxypropyl)-1FI imidazo[4,5-c]quinolin-4- amine (0.75 g), 1,4-butanesultam (0.29 g), copper (I) (68 mg), (No.)-trans-1,2- diaminocyclohexane (42 muL), potassium phosphate (0.79 g) and dioxane (4 mL) were added to a scintillation vial. The vial was flushed with nitrogen, sealed with a Teflon- lined cap, placed in an oil bath, and heated at 110 C for 30 hours. The reaction was cooled to ambient temperature, diluted with chloroform and filtered through a bed of CELITE filter agent. The solvent was evaporated and the residue was purified by column chromatography on a Biotage HorizonNo. High-Performance Flash Chromatography instrument using a silica gel cartridge. The polar component of the eluent was chloroform:methanol:ammonium hydroxide 80:18:2 (CMA). The purification was carried out eluting with chloroform: CMA in a gradient from 99: 1 to 90: 10. Additional purification by recrystallization from acetonitrile provided 0.47 g of 7-(1,1-dioxo- [1,2]thiazinan-2-yl)-2-ethoxymethyl-1-(3-isopropoxypropyl)-1H imidazo[4,5-c]quinolin- 4-amine as pale yellow crystals, mp 172-174 C.

According to the analysis of related databases, 1,2-Thiazinane 1,1-dioxide, the application of this compound in the production field has become more and more popular.

Reference£º
Patent; 3M INNOVATIVE PROPERTIES COMPANY; WO2005/123080; (2005); A2;,
Thiazine – an overview | ScienceDirect Topics
Thiazine | C4H5NS – PubChem

37441-50-2 A common heterocyclic compound, 37441-50-2,1,2-Thiazinane 1,1-dioxide, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

6- (1, 1-Dioxo- [1, 2]-thiazinan-2-yl)-3-hydroxy-4-methoxy- pyridine-2-carboxylic acid 4-fluoro-benzylamide compound 62 To a solution of 3-benzyloxy-6-bromo-4-methoxy-pyridine-2- carboxylic acid 4-fluoro-benzylamide (44.5 mg, 0.1 mmol) in toluene (4 ml) were added 1, 4-butanesultam (16.2 mg, 0.12 mmol), cesium carbonate (65 mg, 0.2 mmol), CuI (1.9 mg, 0.01 mmol), 1, 10-phenanthroline (3.6 mg, 0.02 mmol). Under nitrogen, the mixture was stirred at 100’C overnight. After removal of the solvent under reduced pressure, the residue was dissolved into water (10 mL) and extracted with dichloromethane (3 x 10 mL), and the combined organic layers were dried over anhydrous sodium sulfate. Evaporation of the solvent under reduced pressure provided a residue, which was purified on silica gel column eluting with hexane and ethyl acetate (5: 5) to afford a white solid (45 mg). This product (40 mg) was deprotected using hydrogenolysis in methanol to provide the title compound (30 mg).. 1H NMR (400 MHz, CDC13) : 6 [ppm] 12.22 (s, 1H), 7.90 (br s, 1H), 7.30 (m, 2H), 7.07 (m, 3H), 4.58 (d, 2H), 3.92 (m, 5H), 3.13 (m, 2H), 2.30 (m, 2H), 1.89 (m, 2H). LC/MS : m/z 410.2 (M + H+).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand 1,2-Thiazinane 1,1-dioxide reaction routes.

Reference£º
Patent; VIROCHEM PHARMA INC.; WO2005/42524; (2005); A1;,
Thiazine – an overview | ScienceDirect Topics
Thiazine | C4H5NS – PubChem

In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 37441-50-2,1,2-Thiazinane 1,1-dioxide, as follows.37441-50-2

Step2 A strong glass tube was charged with Pd2(dba)3 (6.4 mg; 0.007 mmol), xantphos (12 mg; 0.02 mmol), 1,2-thiazinane-1,1-dioxide (115 mg; 0.85 mmol), and Cs2CO3 (323 mg; 0.99 mmol).The tube was capped with a rubber septum, evacuated and backfilled with nitrogen. 6-Bromo-1-methyl-1H-indole carboxylic acid ethyl ester (200 mg; 0.71 mmol) in 1 ml of 1,4-dioxane was added through the septum.The septum was replaced with a Teflon screwcap.The tube was sealed, and the mixture was stirred at 100 C. for 64 hours.The reaction mixture was cooled to room temperature, diluted with ethyl acetate (10 ml), filtered, and concentrated in vacuo.The crude material was purified by flash chromatography (silica gel, ethyl acetate-hexane 1:1) to afford 190 mg (66%; m/z 337) of colorless crystals.This compound was dissolved in a mixture of tetrahydrofuran (4 ml), methanol (2 ml) and water (1 ml).To this solution was added dropwise LiOH monohydrate (95 mg; 2.26 mmol) dissolved in 1 ml water and the mixture was stirred at room temperature for 16 h.The reaction mixture was partition between ethyl acetate and water.The aqueous layer was acidified with 2N HCl to ph ~3-4 and extracted with ethyl acetate.The organic layer was washed with brine and dried (Na2SO4) and evaporated in vacuo.Yield 131 mg of 6-(1,1-Dioxo-1lambda6-[1,2]thiazinan-2-yl)-1-methyl-1H-indole-2-carboxylic acid as a white powder (75%); m/z 307.

According to the analysis of related databases, 1,2-Thiazinane 1,1-dioxide, the application of this compound in the production field has become more and more popular.

Reference£º
Patent; Bamberg, Joe Timothy; Gabriel, Tobias; Krauss, Nancy Elisabeth; Mirzadegan, Taraneh; Palmer, Wylie Solang; Smith, David Bernard; US2004/77646; (2004); A1;,
Thiazine – an overview | ScienceDirect Topics
Thiazine | C4H5NS – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 1,2-Thiazinane 1,1-dioxide,37441-50-2, This compound has unique chemical properties. The synthetic route is as follows.,37441-50-2

8-HYDROXY- [1, 6] naphthyridine-7-carboxylic acid methyl ester 1A. 4 (WO 0230930 A2, p. 171) is reacted with one molar equivalent of N-bromosuccinimide in dichloromethane, to yield 5-BROMO-8-HYDROXY- [1, 6] NAPHTLIYRIDINE-7-CARBOXYLIC acid methyl ester, 1A. 5. The phenol is then reacted with p-toluenesulfonyl chloride and triethylamine in CHLOROFONN, FOR example as described in WO 02 30931 A2 p. 72, to give 5-bromo-8- (toluene-4-sulfonyloxy)- [1, 6] naphthyridine-7-carboxylic acid methyl ester 1A. 6. The product is then reacted with [1, 2] thiazinane 1, 1-dioxide 1A. 7 and cuprous oxide in pyridine at reflux, for example as described in WO 0230931 A2, p. 73, to produce 5- (1, 1-DIOXO- 1,2] thiazinan-2-yl)-8- (toluene-4-sulfonyloxy)- [1, 6] naphthyridine-7-carboxylic acid methyl ester 1A. 8. Deprotection, for example by reaction with methanol sodium methoxide in DIMETHYLFORMAMIDE, as described in WO 0230931 A2 p. 74, then affords the phenol 1A. 9.

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 37441-50-2.

Reference£º
Patent; GILEAD SCIENCES, INC.; WO2005/28478; (2005); A1;,
Thiazine – an overview | ScienceDirect Topics
Thiazine | C4H5NS – PubChem

37441-50-2,A common heterocyclic compound, 37441-50-2,1,2-Thiazinane 1,1-dioxide, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

Intermediate 524-Fluoro- 2-(l,l-dioxo-llambda6-[l,2]thiazinan-2-yl)benzonitrile: To a solution of l,l-dioxo[l,2]thiazinane (8.84 g, 65.4 mmol) in DMF (20 mL) and THF (10 mL) was added portion-wise sodium hydride (1.65 g, 65.5 mmol, 95%). After stirring for 30 min, 2,4-difluorobenzonitrile (10.0 g, 72 mmol) was added and the mixture was stirred at 90 C for 2.5 h. The mixture was cooled and concentrated and the residue was purified by flash chromatography eluting with 0%-l 0% EtOAc/hexane to give the title compound as white needles (1.37 g, 8% yield). 1H-NMR (500 MHz, CDCl3) delta: 7.70 (IH, dd, J= 8.8, 5.8 Hz), 7.30 (IH, dd, J= 8.8, 2.4 Hz), 7.15-7.12 (IH, m), 3.72 (2H, t, J= 5.3 Hz), 3.33 (2H, t, J= 6.1 Hz), 2.40-2.35 (2H, m), 2.05-2.01 (2H, m). LCMS [M+H]+ calcd for C11H12N2FO2S: 255.06; found: 255.19.

The chemical industry reduces the impact on the environment during synthesis, 37441-50-2,1,2-Thiazinane 1,1-dioxide,I believe this compound will play a more active role in future production and life.

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2007/58646; (2007); A1;,
Thiazine – an overview | ScienceDirect Topics
Thiazine | C4H5NS – PubChem

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials.37441-50-2,A new synthetic method of this compound is introduced below.37441-50-2

4-Fluoro-2-(l ,1-dioxo-l lambda -[l,2]thiazinan~2-yl)bemonitrile. To a mixture of2,4-difluorobenzonitrile (10.0 g, 72 mmol) and l,l-dioxo-llambda6-[l,2]thiazin-2-ane (8.84 g, 65.4 mmol) in 1:1 tetrahydrofuran/dimethylformamide (40 mL) was added potassium carbonate (9.0 g, 65.4 mmol). The mixture was stirred at 90 0C for 18 h then filtered and concentrated. The residue was purified by flash chromatography (SiO2) eluting with 10%-50% ethyl acetate/hexanes followed by recrystallization from hot ethyl acetate/hexane to give the title compound as white needles (0.537 g, 3% yield). 1H NMR (500 MHz, CD3OD) 5 ppm: 7.70 (IH, dd, J= 8.8, 5.8 Hz), 7.30 (IH, dd, J= 8.8, 2.4 Hz), 7.15-7.12 (IH, m), 3.27 (2H, t, J= 5.3 Hz), 3.33 (2H, t, J= 6.1 Hz), 2.40-2.35 (2H, m), 2.05-2.01 (2H, m). LCMS (M+H) calcd for C11H16N2OF: 255.06; found: 255.19.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 1,2-Thiazinane 1,1-dioxide.

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2007/64316; (2007); A1;,
Thiazine – an overview | ScienceDirect Topics
Thiazine | C4H5NS – PubChem

37441-50-2,A common heterocyclic compound, 37441-50-2,1,2-Thiazinane 1,1-dioxide, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

(39) A mixture of 5-chloro-N-((1-(4-iodophenyl)-1H-imidazol-4-yl)methyl)thiophene-2-carboxamide 1-6 (56 mg, 0.10 mmol), 1,4-butanesultam (52 mg, 0.38 mmol), 8-hydroxyquinoline (6 mg, 0.040 mmol) and K2CO3 (50 mg, 0.36 mmol) in DMSO (1 mL) was degassed before being charged with CuI (10 mg, 0.052 mmol). The mixture in a sealed tube was heated at 130 C. overnight. The mixture was then purified by HPLC to give the titled compound (10 mg). MS 451.1 and 453.1 (M+H, Cl pattern)., 37441-50-2

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand 37441-50-2 reaction routes.

Reference£º
Patent; Millennium Pharmaceuticals, Inc.; US2007/259924; (2007); A1;,
Thiazine – an overview | ScienceDirect Topics
Thiazine | C4H5NS – PubChem