Heterocyclic Building Blocks-Thiomorpholine

128453-98-5, 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. 4-(tert-Butoxycarbonyl)thiomorpholine-3-carboxylic acid, cas is 128453-98-5,the Thiomorpholine compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 4-N-Boc-3-thiomorpholinecarboxylic acid (2.09 g, 8.44 mmol) in methanol (84 ml_) was added HCI (4.0 M in dioxane; 1.07 ml_, 4.28 mmol). The resulting reaction mixture was heated at reflux for 20 hours, cooled, and concentrated in vacuo. The solid residue was dissolved in THF/CH2CI2 (50/30 ml_) and LiBH4 (2.0 M in THF) (10 ml_, 20.0 mmol) was added dropwise over 10 minutes. The reaction mixture was stirred for 5 days before being quenched with slow addition of methanol (-80 ml_). After concentration in vacuo, the residue was dissolved in CH2CI2 and washed with 1 N HCI and brine. The organic layer was dried over Na2SO4, filtered, and concentrated to afford 1.27 g of crude product: 1 H NMR (400 MHz, CDCI3-C/) delta ppm 4.31 (s, 1 H) 4.06 – 4.18 (m, 1 H) 3.69 – 3.75 (m, 1 H) 3.60 – 3.67 (m, 1 H) 3.40 (d, J=13.89 Hz, 1 H) 3.33 (d, J=19.20 Hz, 1 H) 2.72 – 2.84 (m, 2 H) 2.27 (d, J= 12.63 Hz, 1 H) 1.44 – 1.54 (m, 10 H).

If you are interested in these compounds, 128453-98-5, 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; SMITHKLINE BEECHAM CORPORATION; WO2007/98393; (2007); A2;,
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

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).

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; KIM, Kyoung S.; ZHANG, Liping; PURANDARE, Ashok Vinayak; SEITZ, Steven P.; WO2015/77193; (2015); 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

Preparation 75: 4-(3-Methoxy-4-nitrobenzyl)thiomorpholine-1 ,1 -dioxide; [00245] Thiomorpholine 1 ,1 -dioxide (0.242g, 1 .788mmol) and triethylamine (0.19ml_, 1 .341 mmol) were added to a solution of 4-(bromomethyl)-2-methoxy-1 -nitrobenzene (Preparation 74, 0.22g, 0.894mmol) in THF (2.2ml_). The reaction mixture was stirred overnight at room temperature before being concentrated under reduced pressure and purified via Biotage silica gel column chromatography eluting with (DCM/EtOAc 99/1 to 90/10) to afford the title product as a white solid (242mg, 90percent). 1 H NMR (500 MHz, CDCI3): delta 3.00-3.04 (m, 4H), 3.09-3.12 (m, 4H), 3.71 (s, 2H), 3.98 (s, 3H), 7.01 (m, 1 H), 7.09 (m, 1 H), 7.84 (d, J = 8.2Hz, 1 H). LC (Method C)-MS (ESI, m/z) fR 2.03 min, 301 [(M+H+), 100percent].

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; CANCER RESEARCH TECHNOLOGY LIMITED; BAVETSIAS, Vassilios; ATRASH, Butrus; NAUD, Sebastien Gaston Andre; SHELDRAKE, Peter William; BLAGG, Julian; WO2012/123745; (2012); 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

Dissolved a mixture of 1 ,4-dibromobenzene (10.014 g, 42.4 mmol) and thiomorpholine 1,1- dioxide (5.16 g, 38.2 mmol) in dioxane (150 mL), then added Pd(OAc)2 (959 mg, 4.24 mmol), BINAP (racemic) (2.64 g, 4.24 mmol), and Cs2C03 (41.48 g, 127 mmol). The reaction mixture was degassed several times then connected to a reflux condensor under nitrogen and heated to 100 ¡ãC for overnight. The reaction was cooled to RT then filtered through celite, and washed with EtOAc. The resulting solution was concentrated under reduced pressure and the residue was purified by flash chromatography on silica gel (0-50percent EtOAc in hexanes) to yield 6.45 g (50percent) of the desired 4-(4-Bromophenyl)thiomorpholine 1 , 1 -dioxideas a light yellow solid. MS(ES,m/z):292.1 (M + 1)., 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; MERCK SHARP & DOHME CORP.; STACHEL, Shawn; FU, Jianmin; XU, Shimin; PAONE, Daniel; LI, Jing; GINNETTI, Anthony; Lim, John; WO2015/51479; (2015); A1;,
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 a suspension of Intermediate 41 (68.4 mg, 0.146 mmol, 1.0 eq) in anhydrous CH2CI2 (3 mL) was added 1-oxide thiomorpholine hydrochloride (45.6 mg, 0.293 mmol, 2.0 eq) and sodium acetate (24.0 mg, 0.293 mmol, 2.0 eq) and the resulting suspension was stirred at 42 C for 6 h. After cooling to rt, NaBH(OAc)3(62.1 mg, 0.293 mmol, 2.0 eq) was added and the reaction mixture was stirred at rt for 16 h. Additional portions of sodium acetate (12.0 mg, 0.147 mmol, 1.0 eq), 1-oxide thiomorpholine hydrochloride (22.8 mg, 0.147 mmol, 1.0 eq) and NaBH(OAc)3 (31.1 mg, 0.147 mmol, 1.0 eq) were added and the reaction was stirred at 40C for 18 h. Upon cooling to rt, the reaction was quenched with 1 Maqueous NaOH (5 mL) then poured into H20 (15 mL) and extracted with CH2CI2(3 x 15 mL). The combined organic extracts were concentrated in vacuo andpurified by silica gel chromatography using EtOAc/MeOH (1 :0-13:1). The productwas re-dissolved in CH2CI2/MeOH (4:1, 10 mL) and swirled with MP-TMT resin(157 mg, 0.173 mmol) at rt overnight. The solution was filtered and the resinwashed with CH2CI2/MeOH (4:1, 100 mL). The filtrate was concentrated in vacuoand purified a second time by silica gel column chromatography with CH2CI2/MeOH (1:0-12:1) to yield Example S as a white solid (37.6 mg, 45%).1H NMR (300MHz, DMSO-d5) oH. 12.47 (5, 1H), 8.54-8.67 (m, 2H), 8.28 (dd, J=7.4, 0.8 Hz, 1H), 7.98 (5, 1H), 7.64 (d, J=8.1 Hz, 1H), 7.40-7.52 (m, 1H), 4.08-4.19 (m, 4H), 3.81-3.92 (m, 6H), 2.86-3.02 (m, 4H), 2.68-2.80 (m, 4H).19F NMR (282MHz, DMSO-d5) 0F. -58.8 (5, 3F).MS (ESj 571.0 (100%, [M+H]j.

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; 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

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

Example 10 2-[2-(4-Methylpiperazin-1-yl)-benzylidene]-thiomorpholin-3-one Sodium hydride (930 mg, 23.3 mmol of 60% oil dispersion) was washed with hexanes under a nitrogen atmosphere and suspended in 100 mL of anhydrous THF. Thiomorpholin-3-one (1.0 g, 8.55 mmol) was added, followed immediately by 2-(4-methylpiperazin-1-yl)-benzaldehyde (1.58 g, 7.75 mmol). The reaction was then heated to reflux overnight, cooled to room temperature and concentrated in vacuo. The residue was dissolved in methylene chloride and washed with aqueous ammonium chloride (NH4Cl) and saturated brine and then dried with MgSO4. Purification using flash chromatography gave 2-{hydroxy-[2-(4-methylpiperazin-1-yl)phenyl]-methyl}-thiomorpholin-3-one as a white solid, m.p. 137-139 C. Mass spectrum 322 (M+1).

According to the analysis of related databases, 20196-21-8, the application of this compound in the production field has become more and more popular.

Reference£º
Patent; Pfizer INC; US6423708; (2002); B1;,
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 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.

According to the analysis of related databases, 20196-21-8, the application of this compound in the production field has become more and more popular.

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

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

7-Bromo-isochroman-4-one (0.45 g, 2 mmol) and 1,1-dioxothiomorpholine (0.3 g, 2 mmol) were dissolved in 1,2-dichloroethane (30 mL) and added Sodium triacetoxyborohydride (1 g, 20 mmol) was stirred at room temperature for 8 hours. The reaction solution was concentrated to dryness.Purified by silica gel column chromatography,A white solid (0.5 g, 85percent) was obtained.

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; Shanghai Xiangjin Biological Technology Co., Ltd.; Sun Fang; Zhan Youni; (53 pag.)CN108341814; (2018); 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.128453-98-5, 4-(tert-Butoxycarbonyl)thiomorpholine-3-carboxylic acid it is a common compound, a new synthetic route is introduced below., 128453-98-5

o a solution of N-Boc thiomorpholine carboxylic acid (0.803 g, 2.96 mmol) in 16 mL of anhydrous dichloromethane was added O-benzotriazol-1-yl-Lambda/,Lambda/,Lambda/’,Lambda/’-tetramethyluronium tetrafluoroborate (TBTU) (1.03 g, 3.22 mmol) and the solution was stirred for 45 min. A solution of D-serine methyl ester hydrochloride (0.911 g, 5.85 mmol) and Huenig’s base (1.02 mL, 5.85 mmol) in dichloromethane was prepared and added to the reaction mixture. The reaction was left stirring at room temperature overnight. UPLC-MS analysis showed conversion to the product. The reaction was diluted with dichloromethane and extracted with water, dried (Na2SO4), and the solvent was removed. The crude (1.73 g) was taken to the next step without further purification; To a solution of N-Boc thiomorpholine carboxylic acid (0.488 g, 1.97 mmol) and O- benzotriazol-1-yl-Lambda/,Lambda/,Lambda/’,Lambda/’-tetramethyluronium tetrafluoroborate (TBTU) (0.697 g, 2.17 mmol) in 5 mL of anhydrous dichloromethane was added DIPEA (0.7 mL, 3.95 mmol) and the solution was stirred for 30 mins. To a suspension of D-serine methyl ester hydrochloride (0.47 g, 3.95 mmol) in 5 mL of anhydrous dichloromethane was added DIPEA (0.7 mL, 3.95 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 at room temperature overnight.Water was added to the reaction mixture and the two phases were separated. The aqueous layer was extracted with dichloromethane (3X) and the combined organic phases were dried (Na2SO4) and evaporated to dryness. This crude material (1.66 g) was used in the next step without further purification. UPLC-MS: m/z= 349 (M+1 ) (at) t=0.59 min

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 128453-98-5, and friends who are interested can also refer to it.

Reference£º
Patent; SMITHKLINE BEECHAM CORPORATION; WO2007/28654; (2007); 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

T3P (3.61 mL, 6.07 mmol) was added to a solution of 4-amino-2-chlorobenzonitrile (370 mg, 2.43 mmol), 4-(tert-butoxycarbonyl)thiomorpholine-2-carboxylic acid (500 mg, 2.02 mmol), DIEA (1.76 mL, 10.11 mmol) and DMAP (272 mg, 2.22 mmol) in ethyl acetate (10 mL) at room temperature, and the mixture was heated at 60C overnight. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (solvent gradient; 5?60% ethyl acetate/hexane) to give tert-butyl 2-((3-chloro-4-cyanophenyl)carbamoyl)thiomorpholine-4-carboxylate (765 mg, 2.003 mmol, 99%) as an orange oil. 1H NMR (300 MHz, CDCl3):delta 1.38-1.55(9H,m), 2.46-2.64(1H,m), 2.74-2.87(1H,m), 3.34-3.52(2H,m), 3.65(1H,dd,J=14.2,2.8 Hz), 4.03-4.17(1H,m), 4.60(1H,dd,J=14.2,4.0 Hz), 7.60(2H,d,J=3.8 Hz), 7.94(1H,s), 9.14(1H,brs).

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; Takeda Pharmaceutical Company Limited; YAMAMOTO, Satoshi; SHIRAI, Junya; ODA, Tsuneo; IMADA, Takashi; KONO, Mitsunori; SATO, Ayumu; TOMATA, Yoshihide; OCHIDA, Atsuko; ISHII, Naoki; SASAKI, Yusuke; FUKASE, Yoshiyuki; YUKAWA, Tomoya; FUKUMOTO, Shoji; (200 pag.)EP3192791; (2017); A1;,
Thiomorpholine – Wikipedia
Thiomorpholine | C4H9NS – PubChem