Heterocyclic Building Blocks-Thiomorpholine

134676-67-8, 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. N-Boc-2-thiomorpholinecarboxylic Acid, cas is 134676-67-8,the Thiomorpholine compound, it is a common compound, a new synthetic route is introduced below.

Step 1 (+/-)-4-tert-butoxycarbonyl-N-(9-chloro-3,4-dihydro-2H-l,5-benzodioxepin- 7-ylmethyl)-N-isobutyl thiomorpholine-2-carboxamide: The mixture of N-(9-chloro-3,4- dihydro-2H- 1 ,5-benzodioxepin-7-ylmethyl)-2-methylpropan- 1 -amine (150 mg), thiomorpholine-2,4-dicarboxylic acid 4-tert-butyl ester (137 mg), l-ethyl-3-(3- dimethylaminopropyl)carbodiimide hydrochloride (138 mg), and dimethyl aminopyridine (92 mg) in dichloromethane (15 ml) was stirred at room temperature overnight. After the addition of water (10 ml), the mixture was extracted with 10 ml ethyl acetate three times. The organic layer was washed with saturated sodium bicarbonate, water and brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude was purified by column chromatography on silica (20-33% ethyl acetate in hexane) to give the desired product as a resin: MS (m+l) = 499.4.

The chemical industry reduces the impact on the environment during synthesis,134676-67-8,N-Boc-2-thiomorpholinecarboxylic Acid,I believe this compound will play a more active role in future production and life.

Reference£º
Patent; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; ZHOU, Qun-Yong; LI, Ji-da; HUANG, Qi; WO2010/77976; (2010); A2;,
Thiomorpholine – Wikipedia
Thiomorpholine | C4H9NS – PubChem

As a common heterocyclic compound, it belongs to Thiomorpholine compound, name is Thiomorpholine 1,1-dioxide, and cas is 39093-93-1, its synthesis route is as follows.,39093-93-1

Example 4 Preparation of Form A 700.0 g of 6-[3-(4-fluoro-phenyl)-5-methyl-isoxazol-4-ylmethoxy]-nicotinic acid (Ex. 1 step f), 10 L of THF and 469.0 g of 1,1-carbodiimidazol were stirred at ambient temperature for one hour. 407.0 g of thiomorpholine-S,S-dioxide, 12.0 g of 4-dimethylaminopyridine and 340 mL of triethylamine p.a. were added successively and refluxed under stirring over two nights. Additional 82.0 g of thiomorpholine-S,S-dioxide and 68.0 mL of triethylamine p.a. were added and further refluxed under stirring overnight (o.n.). The experiment was cooled down to approx. 30 C. 10 L of desalinated water and 16 L of ethanol were added successively. The emerging solution was cooled down to 20 C., seeded with 12 g of Form A and stirred at ambient temperature for 30 min. The suspension was reduced to 16 L at max. 35 C. In order to replace THF, 20 L of ethanol were added. The suspension was stirred at ambient temperature o.n. and then filtrated. The filter cake was rinsed with 7.4 L of a 1:1 desalinated water/ethanol mixture and dried at 50 C. o.n. yielding 820 g of Form A (86%).

With the complex challenges of chemical substances, we look forward to future research findings about 39093-93-1,belong Thiomorpholine compound

Reference£º
Patent; Hoffmann-La Roche Inc.; Dott, Pascal; Grassmann, Olaf; Kammerer, Michael; Manns, Joachim; Schwitter, Urs; Thomas, Andrew; Wyttenbach, Nicole; US2013/172329; (2013); A1;,
Thiomorpholine – Wikipedia
Thiomorpholine | C4H9NS – PubChem

Name is Thiomorpholine 1,1-dioxide, as a common heterocyclic compound, it belongs to Thiomorpholine compound, and cas is 39093-93-1, its synthesis route is as follows.,39093-93-1

General procedure: A mixture ofmethyl 3-iodobenzoate (1 mmol), corresponding amine (3 mmol), K2CO3(4 mmol), CuI (0.2 mmol) and L-proline (0.4 mmol) in 15 mL of DMSO was heatedat 60 ¡ãC for 8 h. The cooled mixture was pour into 150 ml water, and extractedwith ethyl acetate (3 ¡Á 15 mL), the organic fractions were combined, washedwith saturated brine (2 ¡Á 15 ml) prior to drying over anhydrous sodium sulfate.After filtration and concentrate using a rotary evaporator, the residue was purified by silica gel column chromatographyusing a mixture of petroleum ether/ethyl acetate (20 : 1, v/v) as eluent toafford the desired product.

With the complex challenges of chemical substances, we look forward to future research findings about Thiomorpholine 1,1-dioxide

Reference£º
Article; Li, Zheng; Pan, Miaobo; Su, Xin; Dai, Yuxuan; Fu, Mian; Cai, Xingguang; Shi, Wei; Huang, Wenlong; Qian, Hai; Bioorganic and Medicinal Chemistry; vol. 24; 9; (2016); p. 1981 – 1987;,
Thiomorpholine – Wikipedia
Thiomorpholine | C4H9NS – PubChem

As a common heterocyclic compound, it belongs to quinuclidine compound,Quinuclidine-4-carboxylic acid hydrochloride,40117-63-3,Molecular formula: C8H14ClNO313,mainly used in chemical industry, its synthesis route is as follows.,39093-93-1

To a solution of 2-(4-(bromomethyl)phenyl)-4,4,5 ,5 -tetramethyl- 1,3,2-dioxaborolane (0.50 g, 1.68 mmol) in DMF (8 mL) were added K2C03 (0.58 g, 4.21mmol) and thiomorpholine 1,1-dioxide (0.27 g, 2.02 mmol). The reaction mixture was stirred at rt for 2 h. The reaction mixture was diluted with water and ethyl acetate. The organic layer was separated and washed with brine, dried over MgSO4. The filtrate was concentrated in vacuo to give the title compound as a white solid (0.53 g, 89%). ?H NMR(DMSO-d6) oe 7.65 (d, J= 8.1 Hz, 2 H), 7.35 (d, J= 7.9 Hz, 2 H), 3.68 (s, 2 H), 3.16 -3.01 (m, 4 H), 2.85 (dd, J 6.2, 4.0 Hz, 4 H), 1.29 (s, 12 H); MS(ESIj mlz 352.1 (M + H).

With the synthetic route has been constantly updated, we look forward to future research findings about Thiomorpholine 1,1-dioxide,belong Thiomorpholine compound

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; KIM, Kyoung S.; ZHANG, Liping; PURANDARE, Ashok Vinayak; SEITZ, Steven P.; WO2015/77193; (2015); A1;,
Thiomorpholine – Wikipedia
Thiomorpholine | C4H9NS – PubChem

As a common heterocyclic compound, it belongs to Thiomorpholine compound, name is Thiomorpholine 1,1-dioxide, and cas is 39093-93-1, its synthesis route is as follows.,39093-93-1

Example 5; l-(5-tert-Butyl-3-(thiomorpholine-l,l-dioxide-4-carbonyl)thiophen-2-yl)-3-(4-(2- (methylcarbamoyl)pyridin-4-yloxy)phenyl)urea [0228] To a solution of 6-tert-butyl-l/f-thieno[2,3-cTj[l,3]oxazine-2,4-dione (3.7 g, 15 mmol) in dioxane (30 mL) was added 4-(4-aminophenoxy)-N-methylpicolinamide (3.4 g, 14 mmol), and the reaction mixture was heated at 90 0C for 4 h. The volatiles were evaporated under reduced pressure to give the crude product which was used in the next step without further purification. EPO [0229] To a solution of 5-tert-butyl-2-(3-(4-(rhoyridin-4-yloxy)rhohenyl)ureido)thiorhohene-3- carboxylic acid (ca 14 mmol) in THF (70 mL) were added thiomorpholine 1,1 -dioxide (2.27 g, 16.8 mmol, 1.2 eq), HOBt (2.08 g, 15,4 mmol, 1.1 eq), EDCI (3.22 g, 16.8 mmol, 1.2 eq), and the mixture was stirred at room temperature for 16 h. The volatiles were evaporated under reduced pressure to give the crude product which was extracted with saturated sodium bicarbonate (3 x 40 mL) and ethyl acetate (150 mL). The organic layer was dried and diluted with ethanol (40 mL). Upon concentration of the solution using rotary evaporator, precipitation of solid occurred. The solid was digested with ethanol (70 mL), filtered, washed with ethanol to give the product which was dried under vacuum at 70 0C for 24 h. (yield = 7.2 g, 82percent). 1H NMR (400 MHz, DMSOd6) delta 9.89 (s, IH), 9.63 (s, IH), 8.73 (m, IH), 8.47 (d, J = 6.8 Hz, IH), 7.54 (d, J = 8.8 Hz, 2H), 7.35 (d, J = 2.8 Hz, IH), 7.13 (d, J = 8.8 Hz, 2H), 7.11 (m, IHO, 6.65 (s, IH), 3.93 (m, 4H), 3.27 (m, 4H), 2.75 (d, J = 5.2 Hz3 3H), 1.30 (s, 9H).

With the complex challenges of chemical substances, we look forward to future research findings about 39093-93-1,belong Thiomorpholine compound

Reference£º
Patent; LOCUS PHARMACEUTICALS, INC.; MOORE, JR., William, R.; SPRINGMAN, Eric; MICHELOTTI, Enrique; WO2006/62984; (2006); A2;,
Thiomorpholine – Wikipedia
Thiomorpholine | C4H9NS – PubChem

As a common heterocyclic compound, it belongs to quinuclidine compound,Quinuclidine-4-carboxylic acid hydrochloride,40117-63-3,Molecular formula: C8H14ClNO230,mainly used in chemical industry, its synthesis route is as follows.,39093-93-1

Step g: crystalline (U-dioxo-1 6-thiomorpholin-4-yl)-{6-r3-(4-fluoro-phenyl)-5-methyl-isoxazol-4-ylmethoxyl-pyridin-3-yl|-methanone in anhydrous polymorphic form A (Form A ({drug4a})) To a solution of 6-[3-(4-fluoro-phenyl)-5-methyl-isoxazol-4-ylmethoxy]-nicotinic acid (99 mg, 0.33 mmol (69 mg, 0.2 mmol)) in DMF (300 mu) 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 (17.3 mul, 0.22 mmol). The resulting reaction mixture was stirred for 1 h at room temperature. Concentration and purification by chromatography (Si02, heptane:ethyl acetate = 100:0 to 1: 1) afforded the title compound (73 mg, 55%) as a white solid. MS: m/e = 446.1 [M+H]+.

With the complex challenges of chemical substances, we look forward to future research findings about Thiomorpholine 1,1-dioxide,belong Thiomorpholine compound

Reference£º
Patent; IP Gesellschaft fuer Management mbH; Trinius, Frank; EP2792360; (2014); A1;,
Thiomorpholine – Wikipedia
Thiomorpholine | C4H9NS – PubChem

Name is Thiomorpholine 1,1-dioxide, as a common heterocyclic compound, it belongs to Thiomorpholine compound, and cas is 39093-93-1, its synthesis route is as follows.,39093-93-1

A mixture of thiomorpholine 1,1-dioxide (270 mg, 2.0 mmol) in DMF (10 ml) was prepared at room temperature and sodium hydride (60 wtpercent in oil, 96 mg, 2.40 mmol) added in one portion and the mixture stirred at room temperature for 1h. 1-Bromo-4-(bromomethyl)benzene was then added in one portion and the mixture stirred overnight for 17.5 h under argon. The mixture was then quenched with saturated aqueous ammonium chloride solution (10 ml) and diluted with ethyl acetate (30 ml). The mixture was partitioned and the aqueous layer removed. The organic layers were then washed with 5percent aqueous lithium chloride solution (2x 10 ml), brine (10 ml), dried over magnesium sulphate and the solvent removed under reduced pressure. The crude product was then purified by column (0-5percent methanol/dichloromethane) to afford 4-(4- bromobenzyl)thiomorpholine 1,1-dioxide as a colourless solid (283 mg, 0.93 mmol,47percent). 1H NMR (500 MHz; CDCl3) delta 2.98 (brs, 4H), 3.06 (brs, 4H), 3.60 (5, 2H), 7.20 (d, 2H, J 8.1 Hz), 7.47 (d, 2H, J= 8.3 Hz) ppm.Purity by LCMS (UV Chromatogram, 190-450nm) 95percent, rt = 5.0 min m/z 306 (M+H)+

With the complex challenges of chemical substances, we look forward to future research findings about Thiomorpholine 1,1-dioxide

Reference£º
Patent; UNIVERSITY OF DUNDEE; GILBERT, Ian Hugh; NORCROSS, Neil; BARAGANA RUIBAL, Beatriz; PORZELLE, Achim; WO2013/153357; (2013); A1;,
Thiomorpholine – Wikipedia
Thiomorpholine | C4H9NS – PubChem

As a common heterocyclic compound, it belongs to Thiomorpholine compound, name is Thiomorpholine 1,1-dioxide, and cas is 39093-93-1, its synthesis route is as follows.,39093-93-1

Preparation 14 4-(4-bromobenzyl)thiomorpholine 1,1-dioxide A mixture of thiomorpholine 1,1-dioxide (270 mg, 2.0 mmol) in DMF (10 ml) was prepared at room temperature and sodium hydride (60 wt percent in oil, 96 mg, 2.40 mmol) added in one portion and the mixture stirred at room temperature for 1 h. 1-Bromo-4-(bromomethyl)benzene was then added in one portion and the mixture stirred overnight for 17.5 h under argon. The mixture was then quenched with saturated aqueous ammonium chloride solution (10 ml) and diluted with ethyl acetate (30 ml). The mixture was partitioned and the aqueous layer removed. The organic layers were then washed with 5percent aqueous lithium chloride solution (2*10 ml), brine (10 ml), dried over magnesium sulphate and the solvent removed under reduced pressure. The crude product was then purified by column (0-5percent methanol/dichloromethane) to afford 4-(4-bromobenzyl)thiomorpholine 1,1-dioxide as a colourless solid (283 mg, 0.93 mmol, 47percent). 1H NMR (500 MHz; CDCl3) delta 2.98 (brs, 4H), 3.06 (brs, 4H), 3.60 (s, 2H), 7.20 (d, 2H, J=8.1 Hz), 7.47 (d, 2H, J=8.3 Hz) ppm. Purity by LCMS (UV Chromatogram, 190-450 nm) 95percent, rt=5.0 min, m/z 306 (M+H)+

With the complex challenges of chemical substances, we look forward to future research findings about 39093-93-1,belong Thiomorpholine compound

Reference£º
Patent; Gilbert, Ian Hugh; Norcross, Neil; Baragana Ruibal, Beatriz; Porzelle, Achim; US2015/45354; (2015); A1;,
Thiomorpholine – Wikipedia
Thiomorpholine | C4H9NS – PubChem

Name is Thiomorpholine 1,1-dioxide, as a common heterocyclic compound, it belongs to Thiomorpholine compound, and cas is 39093-93-1, its synthesis route is as follows.,39093-93-1

B. Synthesis of 5?-O-DMT-3?-O-[methyl-(N,N-diisopropyl)]-phosphoramidite-2?-O-thiomorpholino-1, 1-dioxidethionocarbamateuridine. 3?-5?-tetraisopropyldisiloxane Uridine (ChemeGenes), 10 mmol, 4.8 grams was dissolved in 100mls of anhydrous acetonitril in a 500 ml roundbottom flask fitted with a serum stopper. To the reaction 1.9 grams of1, 1?-thiocarbonyldiimidazole (Aldrich) was added with 0.2 grams of 4-(dimethyl)aminopyridine. The reaction washeated using a heat gun and stirred until the reagents had dissolved and the solution was clear. The reaction wasallowed to stir overnight (12 hours). After 12 hours, the reaction mixture was a slurry of crystals. The crystals wereisolated by filtration through a medium sintered glass funnel. The product was washed with cold acetonitrile anddried under vacuum. TLC analysis confirmed that the product was a single species giving 5.97 grams of product(100percent) ESI-Q-TOF mass spectroscopy analysis confirmed the product as the 5?,3?-O-(tetraisopropyldisiloxane-1,3-diyl)-2?-thionoimidazole with a mass of M+1, 598.12 m/e. The product was redissolved in 100 ml of anhydrousacetonitrile by heating using a heat gun. To the reaction was added 11 mmol of thiomorpholine-1, 1-dioxide (TCIAmerica) and 1.1 mmol of 4-(dimethyl)aminopyridine. The reaction was stoppered and stirred for 12 hours. After 12hours, the reaction mixture was a slurry of crystals. The crystals were isolated by filtration through a medium sinteredglass funnel. The product was washed with cold acetonitrile and dried under vacuum. TLC analysis confirmed thatthe product was a single species giving 6.61 grams of product (99percent). ESI-Q-TOF mass spectroscopy analysisconfirmed the product as the 5?,3?-O-(tetraisopropyldisiloxane-1, 3-diyl)-2?-O-thiomorpholino-1, 1-dioxidethionocarbamatewith a mass of M+1, 664.21 m/e. Hydrogen fluoride-pyridine complex (HF:Py 7:3, 7 mL) was carefully toice-cold solution of pyridine (8 mL) in acetonitrile (46.5 mL). The pyridine-HF reagent so formed (32 mL) was thentransferred to the flask with 5?, 3?-O-(tetraisopropyldisiloxane-1,3-diyl)- 2?-O-thiomorpholino-1, 1-dioxidethionocarbamateprotected uridine (10 mmole), and the mixture was stirred at room temperature for 2 hours. The reactionwas quenched with 5percent solution of calcium chloride in water (300 mL). Crude product was extracted with EtOAc(3-5 times), and dried with anhydrous Na2SO4. After filtration organic layer was concentrated to a viscous oil giving3.4 grams (80percent yield) of product shown as a single spot by TLC with a confirmed identity of the 2?-O-thiomorpholino-1, 1-dioxidethionocarbamate protected uridine by ESI-Q-TOF mass spectroscopy with a mass of M+ 1, 422.10 m/e.2?-O-thiomorpholino-1, 1-dioxidethionocarbamate protected uridine (8.0 mmole) was redissolved in anhydrous THF(80 mL), 2,4,6-collidine (60 mmole) and dimethoxytrityl chloride (10.0 mmole) were added, and the mixture wasstirred at room temperature until TLC (CHCl3/MeOH 9:1) showed full disappearance of nucleoside substrate (16-24hours). 2,4,6-Collidine (8.0 mmole) and 1-methylimidazole (4.0 mmole) were added in one portion and N,N-diisopropylmethylphosphonamidicchloride (20 mmol) was added slowly to the reaction mixture over 10-15 minutes. Thereaction mixture was then stirred for another 2 hours. The solvent was removed in vacuo, and the crude productwas purified by column chromatography using hexanes with a gradient of EtOAc (0-50percent).

With the complex challenges of chemical substances, we look forward to future research findings about Thiomorpholine 1,1-dioxide

Reference£º
Patent; Agilent Technologies, Inc.; Dellinger, Douglas J.; Sierzchala, Agnieska; Turner, John; Myerson, Joel; Kupihar, Zoltan; Ferreira, Fernando; Caruthers, Marvin H.; EP2476689; (2015); B1;,
Thiomorpholine – Wikipedia
Thiomorpholine | C4H9NS – PubChem

As a common heterocyclic compound, it belongs to quinuclidine compound,Quinuclidine-4-carboxylic acid hydrochloride,40117-63-3,Molecular formula: C8H14ClNO374,mainly used in chemical industry, its synthesis route is as follows.,39093-93-1

To a well stirred suspension of thiomorpholine 1,1 -dioxide (0.36 g, 2.7 mmol) and potassium carbonate (0.37 g, 2.7 mmol) in acetone (5 mL) was added l-bromo-4- chloromethyl-benzene (0.50 g, 2.4 mmol). The mixture was stirred for 48 hours at room temperature. The mixture was filtered and the volatiles were evaporated. The residue was suspended in ether (100 mL), filtered and evaporated to a solid. The material was purified via chromatography utilizing an ISCO automated purification apparatus (24 g silica gel column 10percent – >;100percent ethyl acetate in hexane). 4-(4-Bromo-benzyl)-thiomorpholine 1,1- dioxide was isolated as a white solid (0.72 g, 97percent). 1H NMR (400 MHz, CDCl3, delta, ppm): 7.47 (d, J=7.6 Hz, 2H), 7.19 (d, J=7.7 Hz, 2H), 3.60 (s, 2H), 3.08-2.94 (m, 8H). MS = 304, 306 (MH)+.

With the synthetic route has been constantly updated, we look forward to future research findings about Thiomorpholine 1,1-dioxide,belong Thiomorpholine compound

Reference£º
Patent; CEPHALON, INC.; CURRY, Matthew A.; DORSEY, Bruce D.; DUGAN, Benjamin J.; GINGRICH, Diane E.; MESAROS, Eugen F.; MILKIEWICZ, Karen L.; WO2010/141796; (2010); A2;,
Thiomorpholine – Wikipedia
Thiomorpholine | C4H9NS – PubChem