Day: November 9, 2020

Thiomorpholine 1,1-dioxide 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., 59801-62-6

After 158 mg of cis-(+)-2-(4-Bromomethylbenzyl)-4-(3,4-dimethoxyphenyl)-4a,5,8,8a-tetrahydro-2H-phthalazin-1 -one obtained in the step 1 in Example 2-1 was dissolved in 20 mL of N,N-Dimethylformamide, 1.10 g of 1,1,-Dioxidothiomorpholine hydrochloride and 1.77 g of Potassium carbonate were added thereto and then the reaction liquid was stirred at room temperature for 9 hours. Water was added to the reaction liquid, and the reaction liquid was subjected to extraction procedure with ethyl acetate. The organic layer was washed with water and saturated saline and dried with anhydrous Magnesium sulfate, and the solvent was evaporated in vacuo. The crude product was purified through silica gel column chromatography to obtain 827 mg of the objective compound as a white amorphous substance. 1H-NMR(CDCl3) delta: 1.9-2.3(3H,m), 2.83(1H,t), 2.9-3.1(9H,m), 3.35(1H,ddd), 3.61(2H,s), 3.92(3H,s), 3.93(3H,s), 5.02(2H,dd), 5.73(2H,m), 6.86(1H,d), 7.2-7.3(3H,m), 7.36(2H,d), 7.46(1H,d) Specific rotation [alpha]D25 = 418.59 (c = 1.0, chloroform)

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. 59801-62-6. We look forward to the emergence of more reaction modes in the future.

Reference£º
Patent; Nippon Shinyaku Co., Ltd.; EP1873147; (2008); 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

[0162] 2-(4-Bromomethyl-phenyl)-4,4,5,5-tetramethyl-[l,3,2]dioxaborolane (1 eq) and DIPEA (2 eq) are dissolved in DCM/MeOH (5: 1 v:v) under N2 and thiomorpho line 1,1 -dioxide (2 eq) is added portionwise. The resulting solution is stirred at room temperature for 16 h. After this time, the reaction is complete. The solvent is evaporated. The compound is extracted with EtOAc and water, washed with brine and dried over anhydrous MgSO i. Organic layers are filtered and evaporated. The final compound is isolated without further purification.

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; GALAPAGOS NV; WIGERINCK, Piet, Tom, Bert, Paul; VAN ‘T KLOOSTER, Gerben, Albert, Eleutherius; (142 pag.)WO2016/165952; (2016); 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

Synthesis of the Compound of the Invention and Comparative ExamplesCompound 1 (the Compound of the Invention); Step 1: 2-(4-Bromomethyl-phenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (1 eq) and DIPEA (2 eq) were dissolved in DCM/MeOH (5:1 v:v) under N2 and thiomorpholine 1,1-dioxide (2 eq) was added portionwise. The resulting solution was stirred at room temperature for 16 h. After this time, the reaction was complete. The solvent was evaporated. The compound was extracted with EtOAc and water, washed with brine and dried over anhyd. MgSO4. Organic layers were filtered and evaporated. The final compound was isolated without further purification.

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; MENET, Christel Jeanne Marie; SMITS, Koen Kurt; US2010/331319; (2010); A1;,
Thiomorpholine – Wikipedia
Thiomorpholine | C4H9NS – 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. 76176-87-9, name is Thiomorpholine-1-oxide hydrochloride. A new synthetic method of this compound is introduced below. 76176-87-9

Intermediate 7 (17.86 g, 44.7 mmol), 1-oxide thiomorpholine hydrochloride (10.5 g, 67.1 mmol, 1.5 eq) and NaOAc (5.87 g, 71.5 mmol, 1.6 eq) weresuspended in anhydrous CH2CI2 (450 mL) under Ar(g). The reaction mixture was then refluxed for 6 h, then cooled down to rt and NaBH(OAc)3 (16.1 g, 76 mmol, 1 .7 eq) was slowly added over 15 mins. The mixture was left to stir at rt for 18 h. The mixture was then re-charged with 1-oxide thiomorpholine hydrochloride (10.5 g, 67.1 mmol, 1.5 eq), NaOAc (5.87 g, 71.5 mmol, 1.6 eq) andNaBH(OAc)3 (16.1 g, 76 mmol, 1.7 eq). After 6 h stirring, the mixture was quenched with H20 (300 mL) and extracted with CH2CI2 (2 x 300 mL). The combined organic extracts were washed with 50% brine (50 mL) then dried over MgSO4 and the solvent was removed in vacuo. Pd-scavenge was carried out in CH2CI2/MeOH (1:1, 100 mL) using MP-TMT resin (18 g, 0.68 mmol/g) over 18 h.The next day, the resin was filtered off, washed with CH2CI2/MeOH (1:1, 20 mL) and the solvent was removed in vacuo. Purification by silica gel column chromatography with EtOAc/MeOH (1:0-4:1) followed by CH2CI2/MeOH (1:0-9:1) yielded Example B as an off-white solid (13.0 g, 58%).1H NMR (300MHz, DMSO-d5) oH. 11.27 (brs, 1H), 8.62 (d, J=3.2 Hz, 2H), 8.18(d, J=7.5 Hz, 1H), 7.44-7.59 (m, 3H), 7.23 (t, J=7.7 Hz, 1H), 4.13 (d, J=4.7 Hz,4H), 3.84-3.93 (m, 4H), 3.83 (5, 2H), 2.84-3.03 (m, 4H), 2.64-2.83 (m, 4H). MS (ESj 503.0 (100%, [M+H]j.

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant. 76176-87-9, we look forward to future research findings about .

Reference£º
Patent; KARUS THERAPEUTICS LTD; SHUTTLEWORTH, Stephen Joseph; SILVA, Franck Alexandre; CECIL, Alexander Richard Liam; ALEXANDER, Rikki Peter; GATLAND, Alice Elizabeth; FINNEMORE, Daniel John; (123 pag.)WO2017/29521; (2017); 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

To the acetonitrile (7.4 mL) solution of thiomorpholine 1,1-dioxide (0.500 g, 3.70 mmol) in ice-cold condition, triphosgene (1.10 g, 3.70 mmol) was added under an argon gas atmosphere , and the mixture was stirred overnight at room temperature. Hexane was added to the reaction solution and a solid obtained by concentration is sonicated. The solid was collected by filtration, washed with hexane, and dried under reduced pressure,The title compound was obtained (white solid, 0.731 g, 3.70 mmol, quantitative).

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; CHIBA UNIVERSITY; YAKULTHONSHA COMPANY LIMITED; TAKAYAMA, HIROMITSU; YASOBU, NAOKO; KITAJIMA, MARIKO; YAEGASHI, TAKASHI; MATSUZAKI, TAKESHI; NAGAOKA, MASATO; HASHIMOTO, SHUSUKE; NISHIYAMA, HIROYUKI; SUGIMOTO, TAKUYA; ONO, MASAHIRO; (176 pag.)JP5829520; (2015); B2;,
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

Example 224-(1,1-Dioxo-thiomorpholine-4-carbonyl)-2-methyl-2H-pyrazole-3-carboxylic acid (2-phenyl-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-amideA mixture of 1-methyl-5-(2-phenyl-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamoyl)-1H-pyrazole-4-carboxylic acid (100 mg, 276 mumol), thiomorpholine-1,1-dioxide (44.8 mg, 331 mumol), diisopropylethylamine (145 mul, 828 mumol) and propylphosphonic anhydride (50percent in ethyl acetate, 407 mul, 690 mumol) in tetrahydrofurane (7.00 ml) is stirred for 4 hours at 70¡ã C. and then for 60 hours at 25¡ã C. under nitrogen atmosphere.The solvent is evaporated and to the residue is added sat. aqueous sodium hydrogencarbonate solution.The mixture is stirred for 20 minutes while a white solid precipitates.The solid is collected by filtration, washed with diethylether and dried affording 4-(1,1-dioxo-thiomorpholine-4-carbonyl)-2-methyl-2H-pyrazole-3-carboxylic acid (2-phenyl-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-amide (112 mg, 84.7percent) as a white solid. mp.: >250¡ã C. MS: m/z=480.2 (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; Flohr, Alexander; Gobbi, Luca; Groebke Zbinden, Katrin; Koerner, Matthias; Peters, Jens-Uwe; US2012/142665; (2012); A1;,
Thiomorpholine – Wikipedia
Thiomorpholine | C4H9NS – PubChem

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., 128453-98-5

To the reaction flask was added 1-tert-butoxycarbonylthiomorpholine-2-carboxylic acid (2.47 g, 10 mmol)And dichloromethane (20 mL),After stirring and dissolving,Ice bath cooling,Triethylamine (1.55 mL, 11 mmol) was added in turn,Isobutyl chloroformate (1.503 g, 11 mmol),After the reaction under ice bath for 1 hour,2,6-dimethylaniline 3a (1.51 g, 12.5 mmol) was added,The reaction was stirred at room temperature for 6 hours.(30 mL) and dichloromethane (20 mL) were added thereto, and the aqueous layer was extracted with dichloromethane (20 mL x 3). The organic phases were combined, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure. Chromatography Separation and Purification (petroleum ether / ethyl acetate (v / v) = 5: 1-1: 1)To give a pale yellow solidTert-butyl 3 – ((2,6-dimethylphenyl) carbamoyl) thiomorpholine-4-carboxylate (40a) (1.57 g, yield 44.7%).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. 128453-98-5. We look forward to the emergence of more reaction modes in the future.

Reference£º
Patent; Sichuan Hai Sike Pharmaceutical Co., Ltd.; Wang Wei; Chen Lei; Wang Wenjing; Wei Yonggang; Liu Zhenhong; Qin Linlin; (74 pag.)CN106928127; (2017); A;,
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 l-methyl-5-(2-phenyl-[l,2,4]triazolo[l,5-a]pyridin-7-ylcarbamoyl)-lH-pyrazole-4- carboxylic acid (100 mg, 276 muiotaetaomicron), thiomorpholine- 1,1 -dioxide (44.8 mg, 331 muiotaetaomicron) , diisopropylethylamine (145 mu, 828 mumol) and propylphosphonic anhydride (50percent in ethyl acetate, 407 mu, 690 muiotaetaomicron) in tetrahydrofurane (7.00 ml) is stirred for 4 hours at 70 ¡ãC and then for 60 hours at 25 ¡ãC under nitrogen atmosphere. The solvent is evaporated and to the residue is added sat. aqueous sodium hydrogencarbonate solution. The mixture is stirred for 20 minutes while a white solid precipitates. The solid is collected by filtration, washed with diethylether and dried affording 4-( 1 , 1 -dioxo-thiomorpholine-4-carbonyl)-2-methyl-2H-pyrazole-3-carboxylic acid (2-phenyl-[l,2,4]triazolo[l,5-a]pyridin-7-yl)-amide (112 mg, 84.7percent) as a white solid, mp.: > 250¡ãC. MS: m/z= 480.2 (M+H+)., 39093-93-1

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; F. HOFFMANN-LA ROCHE AG; FLOHR, Alexander; GOBBI, Luca; GROEBKE ZBINDEN, Katrin; KOERNER, Matthias; PETERS, Jens-Uwe; WO2012/76430; (2012); 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. 114525-81-4, name is (R)-4-(tert-Butoxycarbonyl)thiomorpholine-3-carboxylic acid. This compound has unique chemical properties. The synthetic route is as follows. 114525-81-4

(Scheme F, F-3: where RF-1 and RF-2 are the same and equal to proton, RF-3 is CH3, R5 is 4-[(2,6-dichlorobenzoyl)amino]phenyl and stereochemistry is (R,S)). [C00175] [00415] To a cooled (0 C.) solution of Boc-L-thiomorpholine-3-carboxylic acid ((a) Van Der Auwera, C.; Anteunis, M. J. O. Iit. J. Peptide Protein Res. 1987, 29, 574: (b) Kogami, Y.; Okawa, K. Bull. Chem. Soc. Jpn. 1987, 60, 2963: (c) Larsson U.; Carlson R. ACTA Chemica. Scand. 1994, 48, 517: (d) Carson J. F.; Wong F. F. J. Org. Chem. 1964, 29, 2203.) (Scheme F, F-1: where RF-1 and RF-2 are the same and equal to proton and stereochemistry is (R)) (6.7 g, 27 mmol) in CH2Cl2 (100 mL) was added HOBt (4.0 g, 29.7 mmol), DMAP (700 mg), EDC (5.7 g, 29.7 mmol) and triethylamine (13.5 mL, 97 mmol). The reaction mixture was stirred for 10 min, then the amino acid derivative F-2 (Scheme F, where R5 is 4-[(2,6-dichlorobenzoyl)amino]phenyl, RF-3 is CH3, and stereochemistry is (S)) (10.0 g, 24.7 mmol) was added. After 20 h, volatiles were removed in vacuo and the residue partitioned between 2.5% aqueous HCl (100 mL) and H2O (100 mL). The organic layer was separated and washed saturated aqueous NaHCO3 (100 mL), dried and concentrated in vacuo. Purification of the residue by chromatography on SiO2 (500 g) using CH2Cl2/ethyl acetate (10%) as eluent afforded the title compound (12.31 g) as a solid: 1H NMR (CDCl3) delta 1.44 (9H), 2.35 (1H), 2.70 (3H), 3.13 (2H), 3.33 (1H), 3.77 (3H), 4.22 (1H), 5.00 (1H), 6.48 (1H), 7.18 (2H), 7.31 (3H), 7.44 (1H), 7.56 (2H); 13C NMR (CDCl3) delta 171.6, 168.9, 162.5, 136.5, 135.9, 132.4, 131.0, 130.2, 128.2, 120.5, 81.7, 77.3, 53.3, 52.6, 37.0, 28.2, 26.5; IR (mull) 3296, 2924, 1744, 1685, 1668, 1605, 1536, 1515, 1432, 1412, 1321, 1294, 1260, 1244, 1213, 1195, 1161, 798 cm-1; MS (FAB) m/z (rel. intensity) 598 (M+H, 3), 596 (M+H, 5), Anal. Calcd for C27H31Cl2N3O6S: C, 54.36; H, 5.24; N, 7.04. Found: C, 54.23; H, 5.24; N, 6.86. Corrected for 0.60% H2O, found by Karl Fischer analysis.

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant. 114525-81-4, we look forward to future research findings about .

Reference£º
Patent; Pharmacia & Upjohn Company; Tanabe Seiyaku Co., Ltd.; US6685617; (2004); B1;,
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

1.1.1. 4-[4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzyl]-thiomorpholine-1,1-dioxide 2-(4-Bromomethyl-phenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (1 eq) and DIPEA (2 eq) are dissolved in DCM/MeOH (5:1 v:v) under N2 and thiomorpholine 1,1-dioxide (2 eq) is added portionwise. The resulting solution is stirred at room temperature for 16 h. After this time, the reaction is complete. The solvent is evaporated. The compound is extracted with EtOAc and water, washed with brine and dried over anhydrous MgSO4. Organic layers are filtered and evaporated. The final compound is isolated without further purification.

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; SABOURAULT, Nicolas Luc; DE FAVERI, Carla; SHEIKH, Ahmad; US2015/225398; (2015); A1;,
Thiomorpholine – Wikipedia
Thiomorpholine | C4H9NS – PubChem