Category: Thiomorpholine

Thiomorpholine 1,1-dioxide, A common heterocyclic compound, 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., 39093-93-1

A 5 mL jiW tube equipped with a stir bar was charged with 250 mg of tert-butyl (R)-5-bromo-3-((methyl((S)-5 ,6,7,8-tetrahydroquinolin-8-yl)amino)methyl)-3 ,4-dihydroisoquinoline-2( 1H)-carboxylate(0.514 mmol, 1 equiv), 90.0 mg of thiomorpholine 1,1-dioxide (0.668 mmol, 1.3 equiv), 48.0mg of BNAP(0.077 mmol, 0.15 equiv), 0.25 1 g of Cs2CO3 (0.771 mmol, 1.5 equiv), and 24.0mg of Pd2(dba)3 (0.026mmol, 0.05 equiv) and the system was set under Ar atmosphere by flashing through Ar for 1 h. Then 2.57mL of dioxane (degassed by bubbling through Ar for 1 h) was added. After stirring at 140¡ãC for 3 h in thejiW reactor (normal power), EA was added and the suspension was filtered through celite plug. The cmde product was purified on silica gel column using 0-100percent EA in hexanes as eluent affording 252 mg (91percent) of the product 15. 1H NMR (400 MHz, CDCl3) 8.28 (s, 1H), 7.35 (d, J = 7.6 Hz, 1H), 7.11 (t, J = 7.8 Hz, 1H), 7.07-6.99 (m, 1H), 6.91 (d, J = 7.6 Hz, 1H), 6.80- 6.72 (m, 1H), 4.70 (br s, 0.5H), 4.58 (d, J = 17.1Hz, 1H), 4.50 (br s, 0.5H), 3.89-3.77 (m, 1H), 3.65 (s, 1H), 3.50-3.34 (m, 4H), 3.31 -3.15 (m, 5H), 2.872.61 (m, 4H), 2.47 – 2.20 (m, 1H), 2.23 (s, 3H), 2.02 – 1.80 (m, 3H), 1.66 – 1.56 (m, 1H), 1.50 (s, 9H); LC-MS (ESI-API, 254 nm) 75-95percent MeOH in H20 (0.1percent HCO2H), 3 mm, 1.00 mL/min, C18 (Agilent Zorbax XDB-18, 50mm x 4.6 mm, 3.5 .im), m/z = 541.2 (M + H), t = 0.514 mm., 39093-93-1

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. 39093-93-1. We look forward to the emergence of more reaction modes in the future.

Reference£º
Patent; EMORY UNIVERSITY; LIOTTA, Dennis C.; JECS, Edgars; WILSON, Robert James; NGUYEN, Huy Hoang; KIM, Michelle Bora; WILSON, Lawrence; MILLER, Eric James; TAHIROVIC, Yesim Altas; TRUAX, Valarie; KAISER, Thomas; (311 pag.)WO2018/156595; (2018); A1;,
Thiomorpholine – Wikipedia
Thiomorpholine | C4H9NS – PubChem

Thiomorpholine 1,1-dioxide, A common heterocyclic compound, 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., 39093-93-1

Example 24 {6-[3-(3-Chloro-phenyl)-5-methyl-isoxazol-4-ylmethoxy]-pyridin-3-yl}-(1,1-dioxo-1lambda6-thiomorpholin-4-yl)-methanone To a solution of 6-[3-(3-chloro-phenyl)-5-methyl-isoxazol-4-ylmethoxy]-nicotinic acid (69 mg, 0.2 mmol) in DMF (300 muL) were added 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (71 mg, 0.22 mmol), N,N-diisopropyl ethyl amine (171 muL, 1.0 mmol) and thiomorpholine-S,S-dioxide (0.22 mmol). The resulting reaction mixture was stirred for 1 h at room temperature. Concentration and purification by chromatography (SiO2, heptane:ethyl acetate=100:0 to 1:1) afforded the title compound (80 mg, 87percent) which was obtained as a white solid. MS: m/e=462.1 [M+H]+.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. 39093-93-1. We look forward to the emergence of more reaction modes in the future.

Reference£º
Patent; Hoffmann-La Roche Inc.; Dott, Pascal; Hanlon, Steven Paul; Hildbrand, Stefan; Iding, Hans; Thomas, Andrew; Waldmeier, Pius; US2013/102778; (2013); A1;,
Thiomorpholine – Wikipedia
Thiomorpholine | C4H9NS – 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. 128453-98-5, name is 4-(tert-Butoxycarbonyl)thiomorpholine-3-carboxylic acid. This compound has unique chemical properties. The synthetic route is as follows. 128453-98-5

(b) 3-(pyrrolidine-1-carbonyl)thiomorpholine Triethylamine (3.1 ml). followed by a solution of pyrrolidine (2.0 ml) in 10 ml of tetrahydrofuran, was added at 0 C. under a stream of nitrogen to a solution of 5.0 g of 4-(t-butoxycarbonyl)thiomorpholine-3-carboxylic acid in 100 ml of tetrahydrofuran. After the mixture had been stirred for I hour, a solution of 3.6 g of ethyl cyanophosphate in 10 ml of tetrahydrofuran was added to the mixture and the mixture was stirred for 5 hours. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and the solvent was concentrated under reduced pressure. The residue was recrystallized from ethyl acetate/hexane to yield 461 g (74%) of 4-(t-butoxycarbonyl)-3-(pyrrolidine-1-carbonyl)thiomorpholine.

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant. 128453-98-5, we look forward to future research findings about .

Reference£º
Patent; Sankyo Company Limited; US5021413; (1991); A;,
Thiomorpholine – Wikipedia
Thiomorpholine | C4H9NS – PubChem

Thiomorpholine-1-oxide hydrochloride, A common heterocyclic compound, 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., 76176-87-9

To the stirred solution of [cis-3-(4-amino-5-iodo-pyrrolo [2,3-d]pyrimidin-7-yl)-cyclobutyl] methanol (Step R.1 : 348 mg, 1 .0 mmol) and acetonitrile (70 ml) was added 2- iodoxybenzoic acid (IBX, Atlantic SciTech 86900: 561 mg, 2.0 mmol). The reaction mixture was stirred for 1 h at 80 C. The reaction mixture was filtered at 40 C and the filtrate was concentrated. To the residue was added subsequently DCM (50 ml), diisopropylethylamine (3.43 ml, 20 mmol), 1 -oxo-thiomorpholine hydrochloride (312 mg, 2.0 mmol) and sodium triacetoxyborohydride (637 mg, 3.0 mmol) with stirring at rt. The reaction mixture was stirred for 1 h at rt and then partitioned between 1 M NaHC03 and EtOAc. The combined organic layers were washed with water and brine, dried (Na2S0 ), filtered and concentrated. The residue was purified by silica gel column chromatography (DCM/MeOH/NH3aq, 200:20:1 ) to afford 238 mg of the title compound as pale yellow crystals: HPLC-MS: M+H = 446.2 (R, = 0.41 ) (Method X); TLC; R, = 0.26

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. 76176-87-9. We look forward to the emergence of more reaction modes in the future.

Reference£º
Patent; NOVARTIS AG; IRM LLC; CHEN, Bai; FAIRHURST, Robin Alec; JIANG, Songchun; LU, Wenshuo; MARSILJE III, Thomas H.; MCCARTHY, Clive; MICHELLYS, Pierre-Yves; STUTZ, Stefan; WO2012/120469; (2012); A1;,
Thiomorpholine – Wikipedia
Thiomorpholine | C4H9NS – PubChem

20196-21-8, A common heterocyclic compound, 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., 20196-21-8

Preparation 5 4-(4-Trifluoromethylphenyl)-thiomorpholin-3-one. A mixture of thiomorpholin-3-one (500 mg, 4.27 mmol), 4-trifluoromethyl-1-iodobenzene (1.25 mL, 8.5 mmol) and copper metal (814 mg, 12.8 mmol) was heated in a sealed glass tube at 185-200 C. for 18 hours. The residue was then purified by flash chromatography to give 260 mg of the title product as a white solid. M.p. 85-87 C. Mass spectrum 262 (M-1). 1H-NMR (CDCl3, 400 MHz) d 7.62 (2H, d), 7.37 (2H, d), 3.97 (2H, t), 3.43 (2H, s), 3.01 (2H, t).

The chemical industry reduces the impact on the environment during synthesis, 20196-21-8, I believe this compound will play a more active role in future production and life.

Reference£º
Patent; Gibbs, Megan Ann; Howard, Harry Ralph; Sprouse, Jeffrey Scott; Schachter, Joel Barry; Chappell, Phillip Branch; US2002/49214; (2002); A1;,
Thiomorpholine – Wikipedia
Thiomorpholine | C4H9NS – PubChem

As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 39093-93-1, name is Thiomorpholine 1,1-dioxide. This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below. 39093-93-1

4-Bromomethylbenzeneboronic acid pinacol ester (5.0 g,1.68 mmol), 1,1-dioxide thiomorpholine 2.74 g (2.02 mmol), and potassium carbonate (2.79 g, 2.02 mmol) were added to a flask and added with DMF (25mL). The mixture was stirred at 80oC for 4 hours. The reaction mixture was cooled to rt., and poured into ice water (125 mL), and stirred for 30 min. The mixture was filtered to give 4.72 g of the title compound as white solid (yield of 79.7%).

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant. 39093-93-1, we look forward to future research findings about .

Reference£º
Patent; The National Institutes Of Pharmaceutical Research; YIN, Huijun; YAN, Xu; ZONG, Libin; TIAN, Weixue; ZHENG, Li; DOU, Haoshuai; YANG, Yan; (68 pag.)EP3556761; (2019); A1;,
Thiomorpholine – Wikipedia
Thiomorpholine | C4H9NS – PubChem

(R)-4-(tert-Butoxycarbonyl)thiomorpholine-3-carboxylic acid, A common heterocyclic compound, 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., 114525-81-4

Step a. Referring to Scheme 5-2, a mixture of compound 17 (667 mg, 2.4 mmol), (i^-N-Boc-thiomorpholine-S-carboxylic acid (594 mg, 2.4 mmol) and Et3N (486 mg, 4.8 mmol) in EtOAc (20 mL) was stirred at rt for 2h. Subsequently, the reaction mixture was concentrated and the residue was dried in vacuo to give crude compound 19, which was used for the next step without further purification. LC-MS (ESI): m/z 466.0 (M+Na)+.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. 114525-81-4. We look forward to the emergence of more reaction modes in the future.

Reference£º
Patent; PRESIDIO PHARMACEUTICALS, INC.; LI, Leping; ZHONG, Min; WO2010/65668; (2010); A1;,
Thiomorpholine – Wikipedia
Thiomorpholine | C4H9NS – PubChem

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact.39093-93-1, Thiomorpholine 1,1-dioxide it is a common compound, a new synthetic route is introduced below., 39093-93-1

A mixture of 2-bromo-5-iodopyridine (1.0 g), thiomorpholine 1,1-dioxide (0.51 g), tris(dibenzylideneacetone)dipalladium(0) (0.11 g), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (0.20 g), sodium tert-butoxide (0.85 g) and toluene (30 mL) was stirred under argon atmosphere at room temperature for 4 days. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (420 mg). MS(ESI+): [M+H]+ 290.9.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 39093-93-1, and friends who are interested can also refer to it.

Reference£º
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; Saitoh, Morihisa; Yogo, Takatoshi; Kamei, Taku; Tokunaga, Norihito; Ohba, Yusuke; Yukawa, Takafumi; (191 pag.)US2016/159773; (2016); A1;,
Thiomorpholine – Wikipedia
Thiomorpholine | C4H9NS – PubChem

Thiomorpholine 1,1-dioxide, A common heterocyclic compound, 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., 39093-93-1

A mixture of 4-bromobenzyl bromide (1.0 g, 4.0 mmol), triethylamine (0.84 mL,6.0 mmol) and thiomorpholine 1,1-dioxide (1.09 g, 8.0 mmol) in THF (10 mL) was stirred at ambient temperature for 16 h. The solvent was evaporated and the resultant residue diluted with saturated aqueous sodium bicarbonate solution and extracted with ethyl acetate (2 x 50 mL). The combined organic layer was dried over sodium sulfate, filtered and evaporated to afford the title compound (0.90 g, 74percent). 1H NMR (CDCl3, 300MHz): 7.50-7.44 (m, 2H), 7.22-7.16 (m, 2H), 3.60 (s, 2H), 3.09-3.02 (m, 4H), 3.00-2.94 (m, 4H)., 39093-93-1

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. 39093-93-1. We look forward to the emergence of more reaction modes in the future.

Reference£º
Patent; GENENTECH, INC.; WO2009/151598; (2009); A1;,
Thiomorpholine – Wikipedia
Thiomorpholine | C4H9NS – PubChem

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact.39093-93-1, Thiomorpholine 1,1-dioxide it is a common compound, a new synthetic route is introduced below., 39093-93-1

A) 1,1-Dioxo-thiomorpholine-4-carbonyl Chloride To a solution of thiomorpholine 1,1-dioxide (0.181 g, 0.00105 mol) in dry THF (5 mL) was added DIPEA (0.3 mL, 0.00191 mol) at 0¡ã C. To the resulting mixture was added triphosgene (0.11 g, 0.00037 mol) and the mixture was stirred for 2 h at ambient temperature.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 39093-93-1, and friends who are interested can also refer to it.

Reference£º
Patent; Kilburn, John Paul; Andersen, Henrik Sune; Kampen, Gita Camilla Tejlgaard; Ebdrup, Soren; US2009/118259; (2009); A1;,
Thiomorpholine – Wikipedia
Thiomorpholine | C4H9NS – PubChem