Category: 76176-87-9

76176-87-9, 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 36 (100 mg, 0.24 mmol, 1 .0 eq) in CH2CI2 (10mL) was added thiomorpholine-1-oxide hydrochloride (112 mg, 0.72 mmol, 3.0eq) and sodium acetate (59 mg, 0.72 mmol, 3.0 eq). The reaction mixture washeated to reflux for 2 h, cooled to rt and sodium triacetoxyborohydride (102 mg,0.72 mmol, 2.0 eq) added in one portion. After 16 h at rt, the reaction mixture was partitioned between water (10 mL) and CH2CI2 (15 mL). The aqueous phase was re-extracted with CH2CI2 (2 x 15 mL) and the combined organics were dried over magnesium sulfate, filtered, and concentrated in vacuo. The residue (157mg) was purified by flash chromatography with EtOAc/MeOH (1:0-4:1) to affordExample AK as pale yellow solids (91 mg, 73 %) 1H NMR (DMSO-d5) oH. 11.32 (brs, 1H), 8.83 (d, J=1.9 Hz, 1H), 8.71 (d, J=1.9Hz, 1H), 8.28 (d, J=7.5 Hz, 1H), 7.43-7.66 (m, 3H), 7.26 (t, J=7.7 Hz, 1H), 3.97-4.13 (m, 4H), 3.79-3.93 (m, 6H), 2.94 (quin, J=10.3 Hz, 4H), 2.66-2.83 (m, 4H).MS (ESj 519.0 [M+H].

According to the analysis of related databases, 76176-87-9, the application of this compound in the production field has become more and more popular.

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

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 3-(4-amino-5-iodo-pyrrolo[2,3-d]pyrimidin-7-yl)-cyclobutanone (Intermediate BG; 680 mg, 2.05 mmol), 1.2-dichloroethane (55 ml) and diisopropylethylamine (1.79 ml, 10.25 mmol) was subsequently added 1-oxo-thiomorpholine hydrochloride (638 mg, 4.10 mmol) and sodium triacetoxyborohydride (652 mg, 3.08 mmol) at 0 C. The reaction mixture was stirred for 1 h at room temperature and then poured into the stirred mixture of water (150 ml) and EtOAc (150 ml). The precipitate was filtered and washed with water and EtOAc. The solid collected was dried in vacuo to afford the title compound as beige crystals. HPLC-MS: M+H = 432.1 (R, = 0.43); TLC; Rf = 0 36 (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

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

To a solution of acid 1 (50 mg, 0.1 1 mmol) in DMF (1 mL) was added N- methylmorpholine (49 pL, 0.45 mmol) followed by PyBOP (87 mg, 0.17 mmol). The reaction mixture was stirred for 30 min at rt before addition of thiomorpholine-1 -oxide hydrochloride (35 mg, 0.22 mmol). After 3 h 30 min the reaction mixture was diluted with EtOAc (30 mL), washed with HCI solution (5%, 3 x 10 mL) and brine (10 mL), before being dried over MgS04, filtered and concentrated in vacuo. Purification by flash column chromatography with EtOAc/MeOH (1 :0 to 4:1 ) and subsequent trituration with Et20 afforded FU as pale beige solids (16 mg, 27%). (1390) LCMS (ES): Found 550.9 [M+Hf. (1391) 1H NMR (300 MHz, DMSO-cf6) d: 8.97 (d, J=1.5 Hz, 1 H), 8.86 (d, J=1.3 Hz, 1 H), (1392) 8.42 (dd, J=2.5, 1.4 Hz, 1 H), 8.33 (d, J=2.4 Hz, 1 H), 7.84 (d, J=1.5 Hz, 1 H), 7.75 (d, J=3.6 Hz, 1 H), 7.31 (d, J=3.8 Hz, 1 H), 5.76 (br s, 2H), 4.26-4.38 (m, 1 H), 3.79-3.93 (m, 1 H), 3.61 -3.76 (m, 1 H), 3.47-3.60 (m, 1 H), 2.82-3.05 (m, 3H), 2.71 -2.82 (m, 1 H). 19F NMR (282 MHz, DMSO-cf6) d: -64.80 (s, 3F).

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 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

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

To a solution of thiomorpholine 1-oxide hydrochloride (340 mg) and triethylamine (0.31 mL) in N,N-dimethylformamide (25 mL) were added [2-(7-ethyl-5-{[6-(methylsulfonyl)pyridin-3-yl]oxy}-1H-indol-2-yl)-4,5-dihydro-1,3-thiazol-5-yl]acetic acid (500 mg), 1-hydroxybenzotriazole (300 mg) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (420 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 80:20, volume ratio), and the obtained pale-yellow crystals were recrystallized from tetrahydrofuran-ethyl acetate to give the title compound (354 mg, yield 58%) as colorless crystals. melting point 194-196C. MS 561 (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

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

To a suspension of Intermediate 36 (100 mg, 0.24 mmol, 1 .0 eq) in CH2CI2 (10mL) was added thiomorpholine-1-oxide hydrochloride (112 mg, 0.72 mmol, 3.0eq) and sodium acetate (59 mg, 0.72 mmol, 3.0 eq). The reaction mixture washeated to reflux for 2 h, cooled to rt and sodium triacetoxyborohydride (102 mg,0.72 mmol, 2.0 eq) added in one portion. After 16 h at rt, the reaction mixture was partitioned between water (10 mL) and CH2CI2 (15 mL). The aqueous phase was re-extracted with CH2CI2 (2 x 15 mL) and the combined organics were dried over magnesium sulfate, filtered, and concentrated in vacuo. The residue (157mg) was purified by flash chromatography with EtOAc/MeOH (1:0-4:1) to affordExample AK as pale yellow solids (91 mg, 73 %) 1H NMR (DMSO-d5) oH. 11.32 (brs, 1H), 8.83 (d, J=1.9 Hz, 1H), 8.71 (d, J=1.9Hz, 1H), 8.28 (d, J=7.5 Hz, 1H), 7.43-7.66 (m, 3H), 7.26 (t, J=7.7 Hz, 1H), 3.97-4.13 (m, 4H), 3.79-3.93 (m, 6H), 2.94 (quin, J=10.3 Hz, 4H), 2.66-2.83 (m, 4H).MS (ESj 519.0 [M+H].

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 76176-87-9, and friends who are interested can also refer to it.

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

76176-87-9, 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 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).

According to the analysis of related databases, 76176-87-9, the application of this compound in the production field has become more and more popular.

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

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 acid 1 (50 mg, 0.1 1 mmol) in DMF (1 mL) was added N- methylmorpholine (49 pL, 0.45 mmol) followed by PyBOP (87 mg, 0.17 mmol). The reaction mixture was stirred for 30 min at rt before addition of thiomorpholine-1 -oxide hydrochloride (35 mg, 0.22 mmol). After 3 h 30 min the reaction mixture was diluted with EtOAc (30 mL), washed with HCI solution (5%, 3 x 10 mL) and brine (10 mL), before being dried over MgS04, filtered and concentrated in vacuo. Purification by flash column chromatography with EtOAc/MeOH (1 :0 to 4:1 ) and subsequent trituration with Et20 afforded FU as pale beige solids (16 mg, 27%). (1390) LCMS (ES): Found 550.9 [M+Hf. (1391) 1H NMR (300 MHz, DMSO-cf6) d: 8.97 (d, J=1.5 Hz, 1 H), 8.86 (d, J=1.3 Hz, 1 H), (1392) 8.42 (dd, J=2.5, 1.4 Hz, 1 H), 8.33 (d, J=2.4 Hz, 1 H), 7.84 (d, J=1.5 Hz, 1 H), 7.75 (d, J=3.6 Hz, 1 H), 7.31 (d, J=3.8 Hz, 1 H), 5.76 (br s, 2H), 4.26-4.38 (m, 1 H), 3.79-3.93 (m, 1 H), 3.61 -3.76 (m, 1 H), 3.47-3.60 (m, 1 H), 2.82-3.05 (m, 3H), 2.71 -2.82 (m, 1 H). 19F NMR (282 MHz, DMSO-cf6) d: -64.80 (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

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, TBTU (176 mg, 0.55 mmol) was added in one portion to a stirred solution of 8-(1-(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 MgSO4 and concentrated. The residue was purified by preparative HPLC. The fractions were evaporated to dryness, the residue was dissolved in DCM, dried over MgSO4 and concentrated. The remaining solid was triturated with diethyl ether, filtered, washed with diethyl ether and dried under vacuum at 50 C. to afford 8-[1-(3,5-difluorophenyl)pyrrolidin-2-yl]-2-morpholino-6-(1-oxo-1,4-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)

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; ASTRAZENECA AB; US2012/264731; (2012); 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

To Intermediate 6 (2.77 g, 8.7 mmol, 1 eq), 1AI-thiomorpholin-1-one hydrochloride (1.62 g, 10.4 mmol, 1.2 eq) and NaOAc (853 mg, 10.4 mmol, 1.2eq) in anhydrous CH2CI2 (200 mL) was added NaBH(OAc)3 (2.94 g, 13.9 mmol,1 .6 eq). The reaction mixture was stirred at rt overnight. Then, it was partitioned with 1 N NaOH (50 mL) and H20 (50 mL), and extracted with CH2CI2 (3 x 20 mL). The combined organic extracts were dried over MgSO4, filtered and the solvent was removed in vacuo. Purification by silica gel column chromatography withEtOAc/MeOH (1:0-9:1), then CH2CI2/MeOH (1:0-4:1) yielded Intermediate 8 asa white solid (2.48 g, 68%).1H NMR (300MHz, DMSO-d5) oH. 8.62 (d, J=2.lHz, 1H), 8.51 (d, J=2.3Hz, 1H),4.00 (m, 4H), 3.74-3.84 (m, 6H), 2.83-3.00 (m, 4H), 2.61-2.81 (m, 4H).MS (ESj 422.1 (100%, [M+H]j.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 76176-87-9, and friends who are interested can also refer to it.

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

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

A solution of lambda/-(7-chloro-2-methylpyrazolo[l,5-alpha]pyrimidin-5-yl)-4-(2- hydroxypropan-2-yl)benzamide (2F, 52 mg, 0.151 mmol), thiomorpholine-iS’-oxide hydrochloride (91 mg, 0.557 mmol), and JV,jV-diisopropylethylamine (79 mg, 0.467 mmol) in DMF (1.11 mL) was stirred at 100 0C for 3.5h. After cooling to room temperature, the mixture was diluted with methanol, and was then purified by preparatory HPLC (25-30% MeCNZH2O gradient + 0.01% TFA). Lyophilization of the combined fractions gave the titled compound as a white solid (29.3 mg, 24%). 1H NMR (400 MHz, DMSO-J6) delta ppm 1.45 (s, 6 H), 2.39 (s, 3 H), 2.93 (dd, J=12.13, 1.77 Hz, 2 H), 3.09 – 3.22 (m, 2 H), 3.99 – 4.09 (m, 2 H), 4.40 (d, J=14.40 Hz, 2 H), 6.19 (s, 1 H), 7.43 (s, 1 H), 7.60 (d, J=8.59 Hz, 2 H), 8.00 (d, J=8.59 Hz, 2 H), 10.89 (s, 1 H); ESI-MS: m/z 428.3 (M+H)+.

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; WO2009/123986; (2009); A1;,
Thiomorpholine – Wikipedia
Thiomorpholine | C4H9NS – PubChem