Heterocyclic Building Blocks-Thiomorpholine

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

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

N-(5-bromopentyl)phthalimide (1.2g, 4mmol) and thiomorpholine 1,1-dioxide (1.08g, 80mmol) and DIPEA (2ml, 11mmol) was added 10mL i-PrOH, the temperature was raised to 105 deg. C stirred for 16 hours. LCMS traced the reaction. After completion of the reaction it was concentrated, 50ml of water was added, sonicated, and filtered to give a white solid N-(5-(1,1-dioxothiomorpholin-4-yl)pentyl)phthalimide (1.0g, 97percent yield)., 39093-93-1

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; Shenzen Chipscreen Biosciences Ltd.; Lu, Xianping; Liu, Jindi; Yang, Qianjiao; Li, Zhiping; Pan, Desi; Shan, Song; Zhu, Jiangfei; Wang, Xianghui; Liu, Xiangheng; Ning, Zhiqiang; (30 pag.)CN105481778; (2016); A;,
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

76176-87-9, To a solution of thiomorpholine 1-oxide hydrochloride (140 mg) and triethylamine (0.125 mL) in N,N-dimethylformamide (15 mL) were added [2-(7-methyl-5-{[6-(methylsulfonyl)pyridin-3-yl]oxy}-1H-indol-2-yl)-4,5-dihydro-1,3-thiazol-5-yl]acetic acid (200 mg), 1-hydroxybenzotriazole (121 mg) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (172 mg) under ice-cooling, and the mixture was stirred under ice-cooling and then at room temperature for 15 hr. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with aqueous sodium hydrogen carbonate solution and saturated brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography (ethyl acetate:methanol = 100:0 to 75:25, volume ratio), and the obtained pale-yellow crystals were recrystallized from ethyl acetate-hexane to give the title compound (104 mg, yield 42%) as colorless crystals. melting point 157-160C. MS 547 (MH+).

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; Takeda Pharmaceutical Company Limited; EP2371826; (2011); 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

[00227] To a solution of 4-(tert-butoxycarbonyl)thiomorpholine-2-carboxylic acid (300 mg, 1.2 mmol) in THF (6 ml) was dded 4-chloroaniline (170 mg, 1.3 mmol), N-(3- dimethylaminopropyl)-N ?-ethylcarbodiimide hydrochloride (350 mg, 1.8 mmol), N,Ndiisopropylethylamine (0.64 ml, 3.6 mmol), and 4 N,N-diisopropylethylamine (29 mg, 0.24 mmol). The reaction stuffed overnight at room temperature. The reaction was poured into ethyl acetate, and washed with iN HC1, saturated sodium bicarbonate solution and brine. The organic layer was dried over magnesium sulfate, filtered, and concentrated. The crude residue was purified by column chromatography eluting with 10-30% ethyl acetate in hexanes to give the title compound as a colorless gum (296 mg, yield 68%).

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 .

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Patent; THE REGENTS OF THE UNIVERSITY OF MICHIGAN; BOARD OF TRUSTEES OF MICHIGAN STATE UNIVERSITY; LARSEN, Scott, D.; NEUBIG, Richard; HAAK, Andrew; HUTCHINGS, Kim; RAJESWARAN, Walajapet; (156 pag.)WO2016/73847; (2016); 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. 76176-87-9, name is Thiomorpholine-1-oxide hydrochloride. 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. 76176-87-9

To a solution of compound 1 (21.0 mg, 0.0467 mmol, 1.0 eq) in DMF (1 ml_) was added A/,A/-diisopropylethylamine (32.6 pL, 0.187 mmol, 4.0 eq), HATU (26.7 mg, 0.0701 mmol, 1.5 eq) and thiomorpholine-1 -oxide hydrochloride (2) (14.6 mg, 0.0935 mmol, 2.0 eq). The reaction was stirred at room temperature for 17.5 h then diluted with EtOAc (10 ml_), washed with 1 M HCI (2 x 10 ml_) and brine (10 ml_), dried over MgS04, filtered and concentrated in vacuo. Purification by silica gel chromatography using hexane/EtOAc/MeOH (1 :0:0 – 0:1 :0 – 0:9: 1 ) yielded compound FD as a white solid (17.6 mg, 68%). (1239) LCMS (ES): Found 550.9 [M+Hf. (1240) 1H NMR (300MHz, DMSO-cf6), d: 8.88 (d, J=1.3 Hz, 1 H), 8.45 (dd, J=2.6, 1.5 Hz, 1 H), 8.36 (d, J=2.6 Hz, 1 H), 7.85 (d, J=9.4 Hz, 1 H), 7.81 (d, J=9.4 Hz, 1 H), 7.75 (d, J=3.8 Hz, 1 H), 7.32 (d, J=3.8 Hz, 1 H), 5.72-5.80 (m, 2H), 4.34-4.48 (m, 1 H), 3.89-4.06 (m, 2H), 3.66-3.84 (m, 1 H), 2.75-3.1 1 (m, 4H). (1241) 19F NMR (282MHz, DMSO-cf6), d: -64.79 (s, 3F).

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 LIMITED; SHUTTLEWORTH, Stephen Joseph; GATLAND, Alice Elizabeth; FINNEMORE, Daniel John; ALEXANDER, Rikki Peter; SILVA, Franck; CECIL, Alexander; (233 pag.)WO2019/166824; (2019); 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.76176-87-9, Thiomorpholine-1-oxide hydrochloride it is a common compound, a new synthetic route is introduced below., 76176-87-9

Example 1.048-[l-(3,5-difluorophenyl)pyrrolidin-2-yl]-2-morpholino-6-[(l-oxidothiomorpholin-4- yl)carbonyl] -4H-chromen-4-oTBTU (176 mg, 0.55 mmol) was added in one portion to a stirred solution of 8-(l-(3,5- difluorophenyl)pyrrolidin-2-yl)-2-morpholino-4-oxo-4H-chromene-6-carboxylic acid (125 mg, 0.27 mmol) and DIPEA (0.286 mL, 1.64 mmol) at room temperature and stirred for 2.5 h. Thiomorpholine 1 -oxide hydrochloride (85 mg, 0.55 mmol) was added to the reaction mixture and stirring was continued for 3 h. The reaction mixture was diluted with DCM, washed with water, brine, dried over MgSC^ and concentrated. The residue was purified by preparative HPLC. The fractions were evaporated to dryness, the residue was dissolved in DCM, dried over MgSC^ and concentrated. The remaining solid was triturated with diethyl ether, filtered, washed with diethyl ether and dried under vacuum at 50C to afford 8-[l-(3,5-difluorophenyl)pyrrolidin-2-yl]-2-morpholino-6-(l-oxo-l,4- thiazinane-4-carbonyl)chromen-4-one (87 mg, 57%) as a pale beige solid.Mass Spectrum: m/z [M+H]+ = 558.Proton NMR Spectrum : (DMSO-d6) 1.75-1.86 (m, 1H), 1.98-2.08 (m, 2H), 2.14 (bs, 0.5H), 2.51-2.58 (m partially hidden by DMSO-d5, 1H), 2.64 (bs, 1H), 2.81 (bs, 1.5H), 2.98 (bs, 1H), 3.27 (bs, 1H), 3.40 (bs, 1H), 3.49-3.65 (m, 5H), 3.64-3.83 (m, 6H), 4.21 (bs, 0.5H), 4.34 (bs, 0.5H), 5.25 (d, 1H), 5.62 (s, 1H), 6.13 (d, 2H), 6.34 (t, 1H), 7.18 (s, 1H), 7.87 (d, 1H)

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; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; BARLAAM, Bernard, Christophe; DEGORCE, Sebastien Louis; LAMBERT-VAN DER BREMPT, Christine Marie Paul; LOHMANN, Jean-Jacques Marcel; PLE, Patrick; WO2012/140419; (2012); 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. 76176-87-9, name is Thiomorpholine-1-oxide hydrochloride. 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. 76176-87-9

To the stirred solution of [cis-3-(4-amino-5-iodo-pyrrolo [2,3-d]pyrimidin-7-yl)-cyclobutyl] methanol (Intermediate M: 348 mg, 1.0 mmol) and acetonitrile (70 mL) was added IBX (Atlantic SciTech 86900: 561 mg, 2.0 mmol, 2 eq). The reaction mixture was stirred for 1 h at 80 C. Th e reaction mixture was filtered at 40 C and the filtrate was concentrated. To the residue was added subsequently DCM (50 ml_), ethyl-diisopropyl-amine (3.43 ml_, 20 mmol, 20 eq), 1-oxide thiomorpholin hydrochloride (312 mg, 2.0 mmol, 2 eq) and sodium triacetoxyborohy- dride (637 mg, 3.0 mmol, 3 eq) with stirring at rt. The reaction mixture was stirred for 1 h at rt and then partitioned between NaHC03 1M and EtOAc. The combined organic layers were washed with water and brine, dried (Na2S04), 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 (Rt = 0.41) (Method X); TLC; Rf = 0.26 (DCM/MeOH/NH3aq, 200:20: 1).

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; NOVARTIS AG; IRM LLC; CHEN, Bei; FAIRHURST, Robin, Alec; FLOERSHEIMER, Andreas; FURET, Pascal; GUAGNANO, Vito; JIANG, Songchun; LU, Wenshuo; MARSILJE, Thomas, H.; MCCARTHY, Clive; MICHELLYS, Pierre-Yves; STAUFFER, Frederic; STUTZ, Stefan; VAUPEL, Andrea; WO2011/29915; (2011); 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

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 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+).

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; 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. 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 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).

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; WO2007/98393; (2007); A2;,
Thiomorpholine – Wikipedia
Thiomorpholine | C4H9NS – PubChem