Heterocyclic Building Blocks-Thiomorpholine

123-90-0, 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., 123-90-0

9.98 g of thiomorpholine and 14.8 g of triflic anhydride were stirred together in DCM at room temperature for 2 hours. The reaction was then partitioned between 1 M K2C03 (aq) and DCM. The organic layer was separated and dried by passing through a hydrophobic frit, then concentrated in vacuo. 13.82 g of the resultant oil was stirred with 85.2 g of oxone in 50 mL of methanol and 50 mL of water for 18 h at room temperature. The reaction was then filtered and washed with methanol and the filtrate concentrated. This was then partitioned between water and EtOAc and the aqueous layer washed 3 times with EtOAc. The combined organic extracts were then dried (MgS04) and concentrated to produce a white solid. This was then stirred at room temperature with 40 g of K2C03 in 80 mL of methanol for 18 h. The methanol was then removed in vacuo and the remains partitioned between DCM and sat. K2CO3 (aq). The combined organic extracts were passed through a hydrophobic frit and concentrated in vacuo to produce the title compound, 3.51 g.

The chemical industry reduces the impact on the environment during synthesis, 123-90-0, I believe this compound will play a more active role in future production and life.

Reference£º
Patent; ARROW THERAPEUTICS LIMITED; WO2005/89771; (2005); A1;,
Thiomorpholine – Wikipedia
Thiomorpholine | C4H9NS – PubChem

39093-93-1, 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

Step 1: preparation of compound 15-2: To a solution of compound 15-1 (541 mg, 4.0 mmol) and Et3N (1.21 g, 12.0 mmol) in THF (20.0 mL), a solution of triphosgene (1.42 g, 4.8 mmol) in THF (5.0 mL) was added dropwise. After the mixture was stirred at rt o.n., water was added and it was extracted with EtOAc. The organic layer was combined and washed with brine, dried over Na2S04, filtered. Solvent was removed and the residue was purified by column chromatography to give a white solid (760 mg, yield: 96percent). HNMR (400 MHz, DMSO- 6) ^ 4.23 (m, 2H), 4.08-4.14 (m, 2H), 3.39-3.48 (m, 1H), 3.13-3.15 (m, 4H), 1.18-1.27 (m, 2H).

According to the analysis of related databases, 39093-93-1, the application of this compound in the production field has become more and more popular.

Reference£º
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC; CHEN, Huifen; CRAWFORD, Terry; MAGNUSON, Steven, R.; NDUBAKU, Chudi; WANG, Lan; WO2013/113669; (2013); 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

Production Example 4 Compound J7-4 9-(4-Isopropyl-piperazin-1-yl)-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile [0519] trifluoro-methane sulfonic acid 3-cyano-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazol-8-yl ester (Compound B1, 30 mg, 0.069 mmol) was dissolved in 1,4-dioxane (1 mL), added with thiomorpholine 1,1-dioxide (19 mg, 2 eq.), Pd2dba3 (6.3 mg, 0.1 eq.), BINAP (8.6 mg, 0.2 eq.) and K3PO4 (29 mg, 2 eq.), and stirred at 100¡ã C. all night and all day. The reaction solution was poured into water, and then extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over sodium sulfate. The drying agent was removed by filtration and the residues obtained after concentration under reduced pressure were purified by silica gel column chromatography (ethyl acetate/hexane) to obtain the Compound B2-10 (8-(1,1-dioxothiomorpholino)-6,6-dimethyl-11-oxo-6,11 dih dro-5H-benzo b carbazole-3-carbonitrile) (white powder, 2.1 mg, 7percent)), the title compound was synthesized from the Compound J6 and 1-isopropyl-piperazine. [0521] 1H-NMR (270 MHz, DMSO-d6) delta: 12.80 (1H, s), 8.33 (1H, d, J=7.6 Hz), 8.02 (1H, s), 7.66 (3H, m), 7.33 (1H, d, J=8.2 Hz), 3.21 (4H, br), 2.66 (5H, m), 1.72 (6H, s), 1.02 (6H, d, J=6.3 Hz). [0522] LCMS: m/z 413 [M+H]+ [0523] HPLC retention time: 1.38 minutes (analysis condition S), 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; Furumoto, Kentaro; Shiraki, Koji; Hirayama, Tomoaki; US2013/143877; (2013); 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. 39093-93-1, name is Thiomorpholine 1,1-dioxide. A new synthetic method of this compound is introduced below. 39093-93-1

tert-Butyl thiomorpholine-4-carboxylate (1.91 g, 9.42 mmol) was dissolved in dichloromethane (50 ml); m-chloroperbenzoic acid (5.0 g, 19 mmol) was gradually added while cooled with ice bath, stirred, and under nitrogen atmosphere; and the reaction mixture was stirred at room temperature for 12 hours. After addition of a saturated aqueous solution of sodium thiosulfate, the reaction mixture was kept stirred for a while; and this was subjected to extraction with ethyl acetate, washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. Triethylamine (8.1 ml, 58 mmol) were added to the obtained crystals; and the reaction mixture was stirred at room temperature. tert-Butoxycarbonyl dicarbonate (13.3 ml, 58 mmol) was added thereto; and the reaction mixture was stirred at room temperature for 10 hours. The reaction mixture was concentrated under reduced pressure; and the obtained crystals were suspended with a solvent mixture of diethyl ether: ethanol = 10: 1, filtered off, washed with diethyl ether and dried under aeration to yield the title compound as colorless crystals (2.03 g, 8.63 mmol, 91.6percent). 1H-NMR Spectrum (DMSO-d6) delta (ppm): 1.40 (9H, s), 3.09 (4H, t, J=5.2 Hz), 3.72 (4H, t, J=5.2 Hz).

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; Eisai Co., Ltd.; EP1522540; (2005); 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. 134676-67-8, name is N-Boc-2-thiomorpholinecarboxylic Acid. This compound has unique chemical properties. The synthetic route is as follows. 134676-67-8

Synthesis of Example 32 Thiomo holine-2,4-dicarboxylic acid 4-tert-butyl ester (10 g, 40.43 mmol) is dissolved in a mixture of dichloromethane (50 mL) and methanol (40 inL) and cooled to 0 C under N2. A solution of trimethylsilyldiazomethane (2M in diethyl ether, 44.5 mL, 89 mmol) is added dropwise with stirring, the mixture allowed to warm to room temperature and stirred overnight. The solvent is removed under vacuum, the residue dissolved in ethyl acetate and washed with water, dried over magnesium sulphate and the solvent removed under vacuum to give compound 32-1.Yield: 10.5 gES mass spectrum: [M+H-tBu]+ = 206Retention time HPLC : 1.76 min (UPLC Method 1 ), 134676-67-8

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant. 134676-67-8, we look forward to future research findings about .

Reference£º
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; GIOVANNINI, Riccardo; HAMPRECHT, Dieter; KISTLER, Barbara; LINGARD, Iain; WO2012/80456; (2012); A1;,
Thiomorpholine – Wikipedia
Thiomorpholine | C4H9NS – PubChem

39093-93-1, 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

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.

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; MENET, Christel Jeanne Marie; SMITS, Koen Kurt; US2010/331319; (2010); 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

Step 1. Preparation of (S)-benzyl 4-((lR,3aS,5aR,5bR,7aR,l laS,l lbR,13aR,13bR)-3a- ((2-( 1 , 1 -dioxidothiomorpholino)-2-oxoethyl)amino)-5 a,5b,8, 8, 11 a-pentamethyl- 1 -(prop- l-en-2-yl)-2,3,3a,4,5,5a,5b,6,7,7a,8,l l,l la,l lb,12,13,13a,13b-octadecahydro-lH- cyclopenta[a]chrysen-9-yl)-l-(fluoromethyl)cyclohex-3-enecarboxylate. In a 1 dram vial with PTFE lined screw cap were combined 2- (((lR,3aS,5aR,5bR,7aR,l laS,l lbR,13aR,13bR)-9-((S)-4-((benzyloxy)carbonyl)-4- (fluoromethyl)cyclohex- 1 -en- 1 -yl)-5a,5b, 8, 8, 11 a-pentamethyl- 1 -(prop- 1 -en-2-yl)- 2,3,3a,4,5,5a,5b,6,7,7a,8,l l,l la,l lb,12,13,13a,13b-octadecahydro-lH- cyclopenta[a]chrysen-3a-yl)amino)acetic acid, TFA (0.025 g, 0.030 mmol) with thiomorpholine 1,1-dioxide (10.20 mg, 0.075 mmol) and HATU (0.029 g, 0.075 mmol) in THF (1 mL). To the mixture was added DIPEA (0.026 mL, 0.151 mmol), and the resulting solution was agitated overnight at rt. The crude mixture was purified by reverse phase preparative HPLC (Prep HPLC Method 16) to give the product (0.0269 g, 94percent yield) as a white powder TFA salt. LCMS: m/z 831.5 (M+H)+, 2.50 min (method 1).

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; BRISTOL-MYERS SQUIBB COMPANY; SIT, Sing-Yuen; CHEN, Yan; CHEN, Jie; SWIDORSKI, Jacob; VENABLES, Brian Lee; SIN, Ny; MEANWELL, Nicholas A.; REGUEIRO-REN, Alicia; HARTZ, Richard A.; XU, Li; LIU, Zheng; WO2015/157483; (2015); 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

To a solution of N-Boc thiomorpholine carboxylic acid (1.36 g, 5.51 mmol) in dichloromethane (13.6 ml) were added under N2, at r.t., TBTU (1.95 g, 6.06 mmol) and DIPEA (1.92 ml, 11.02 mmol) and the solution was stirred for 30 mins. To a suspension of L-serine methyl ester hydrochloride (1.71 g, 11.02 mmol) in dichloromethane (13.6 ml) was added DIPEA (1.92 ml, 11.02 mmol) and the resulting solution was stirred for 30 mins. Then the solution containing the serine free base was added to the reaction mixture and it was left stirring for 16 hrs. Water was added to the reaction mixture and the aqueous layer was extracted with dichloromethane (x3) and the combined organic phases were dried (Na2SO4) and evaporated to dryness. The crude title compound (3.87 g) was used in the next step without further purification. UPLC/MS: m/z= 371 (M+Na); 349 (M+1 ); 293 (M-fBu); 249 (M-BOC+1 ) (at) t=0.59 min

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; SMITHKLINE BEECHAM CORPORATION; WO2007/28654; (2007); 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

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).

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

20196-21-8, 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. Thiomorpholin-3-one, cas is 20196-21-8,the Thiomorpholine compound, it is a common compound, a new synthetic route is introduced below.

Preparation 6 4-Benzylthiomorpholin-3-one Under a nitrogen atmosphere in a flame-dried flask, sodium hydride (4.65 g, 0.1 05 mol, 54% oil dispersion) was added to 150 mL of anhydrous dimethylformamide (DMF), and the suspension was cooled to 0 C. Thiomorpholin-3-one (11.7 g, 0.1 mol) was added in portions over 30 minutes with stirring. After gas evolution had stopped (ca. 30 minutes), benzyl chloride (12.1 g, 0.105 mol) in DMF (50 mL) was added and stirring was continued at room temperature overnight. The reaction was then warmed to 80 C. for 15 minutes and cooled. Water (250 mL) was added and the mixture was extracted with chloroform which was dried (MgSO4) and concentrated in vacuo to an oil. The oil was triturated with ethyl ether (Et2O) and cooled by dry ice to give the product, 12.75 g as a solid, m.p. 60-62 C. Recrystallization of 5 g from 100 mL of Et2O gave 3.5 g of pure product, m.p. 62-63 C. along with a second crop of 0.75 g with m.p. 62-63 C.

If you are interested in these compounds, 20196-21-8, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

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