Heterocyclic Building Blocks-Thiomorpholine

39093-93-1, Thiomorpholine 1,1-dioxide is a Thiomorpholine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

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+)., 39093-93-1

39093-93-1 Thiomorpholine 1,1-dioxide 6484228, aThiomorpholine compound, is more and more widely used in various fields.

Reference£º
Patent; F. HOFFMANN-LA ROCHE AG; FLOHR, Alexander; GOBBI, Luca; GROEBKE ZBINDEN, Katrin; KOERNER, Matthias; PETERS, Jens-Uwe; WO2012/76430; (2012); A1;,
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39093-93-1, Thiomorpholine 1,1-dioxide is a Thiomorpholine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,39093-93-1

Example 39Synthesis of 3-{3-[4-(1-Aminocyclobutyl)phenyl]-5-[3-(1,1-dioxidothiomorpholin-4-yl)phenyl]-3H-imidazo[4,5-b]pyridin-2-yl}pyridin-2-amine trihydrochloride Step 14-(3-Bromophenyl)thiomorpholine 1,1-dioxideA mixture of 1,3-dibromobenzene (242 muL, 2.00 mmol), thiomorpholine 1,1-dioxide (270 mg, 2.00 mmol), Pd2(dba)3 (45.8 mg, 0.0500 mmol), rac-BINAP (96.3 mg, 0.150 mmol) and NaOtBu (231 mg, 2.40 mmol) in toluene was heated at 80¡ã C. for 11 hours under nitrogen. After cooling to room temperature, the mixture was diluted with DCM and filtered through a Celite pad. The combined filtrate and washings were concentrated. The residue was purified by silica gel column chromatography (EtOAc/hexane=90:10–>80:20–>75:25) to afford desired product (281 mg, 48.4percent) as pale yellow solid.400 MHz 1H-NMR (CDCl3) delta: 7.16 (t, J=8.4 Hz, 1H), 7.07-7.02 (m, 2H), 6.85-6.80 (m, 1H), 3.95-3.76 (m, 4H), 3.20-3.02 (m, 4H).

As the paragraph descriping shows that 39093-93-1 is playing an increasingly important role.

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Patent; ArQuele, Inc.; US2012/329791; (2012); A1;,
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76176-87-9, Thiomorpholine-1-oxide hydrochloride is a Thiomorpholine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,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.

The synthetic route of 76176-87-9 has been constantly updated, and we look forward to future research findings.

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;,
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Thiomorpholine 1,1-dioxide, cas is 39093-93-1, it is a common heterocyclic compound, the Thiomorpholine compound, its synthesis route is as follows.

Example 1 Step 3: (1,1-Dioxo-thiomorpholin-4-yl)-[5-(1-isopropyl-piperidin-4-yloxy)-1-(2,2,2-trifluoro-ethyl)-1H-indol-2-yl]-methanone A mixture of 5-(1-isopropyl-piperidin-4-yloxy)-1-(2,2,2-trifluoro-ethyl)-1H-indole-2-carboxylic acid, hydrochloric salt with one equivalent of lithium chloride (650 mg, 1.0 eq.), 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethylurunium tetrafluoroborate (563 mg, 1.2 eq.), thiomorpholine-1,1-dioxide (purchased at Syntec, ref. M1201) and diisopropylethylamine (1.22 mL, 5 eq.) in dimethylformamide was stirred at room temperature for 24 h and then partitioned between an aqueous solution of sodium hydrogenocarbonate and ethyl acetate. The aqueous layer was extracted with ethyl acetate and the combined organic layers were washed with water and brine, dried over sodium sulfate, filtered, evaporated in vacuo and purified on silica eluting with dichloromethane/methanol/ammoniac. One fraction was isolated and dried in vacuo, to yield 468 mg (66percent) of the desired product as off-white solid. MS (m/e): 502.5 (MH+, 100percent). ; Example20 Step 4: (1,1-Dioxo-1lambda6-thiomorpholin-4-yl)-(5-hydroxy-1-isopropyl-1H-indol-2-yl)-methanone In analogy to the procedure described for the synthesis of example 1, step 3, the title compound was synthesised from 5-Hydroxy-1-isopropyl-1H-indole-2-carboxylic acid (Example 20, step 3) and thiomorpholine-1,1-dioxide (purchased at Syntec, ref. M1201). The desired product was obtained in a yield of 75percent as white solid. MS (m/e): 335.5 (M-H, 100percent)., 39093-93-1

As the rapid development of chemical substances, we look forward to future research findings about 39093-93-1

Reference£º
Patent; Nettekoven, Matthias; Plancher, Jean-Marc; Richter, Hans; Roche, Olivier; Rodriguez Sarmiento, Rosa Maria; Taylor, Sven; US2007/123526; (2007); A1;,
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Thiomorpholine-1-oxide hydrochloride, cas is 76176-87-9, it is a common heterocyclic compound, the Thiomorpholine compound, its synthesis route is as follows.,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)

As the rapid development of chemical substances, we look forward to future research findings about 76176-87-9

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;,
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76176-87-9, Thiomorpholine-1-oxide hydrochloride is a Thiomorpholine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,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).

As the paragraph descriping shows that 76176-87-9 is playing an increasingly important role.

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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;,
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Thiomorpholin-3-one, cas is 20196-21-8, it is a common heterocyclic compound, the Thiomorpholine compound, its synthesis route is as follows.

Preparation 6 4-Benzylthiomorpholin-3-one Under a nitrogen atmosphere in a flame-dried flask, sodium hydride (4.65 g, 0.105 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. 60-42 C. Recrystallization of 5 g from 100 mL of Et2O gave 3.5 g of pure product, m.p. 62-43 C. along with a second crop of 0.75 g with m.p. 62-43 C., 20196-21-8

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Patent; Pfizer INC; US6423708; (2002); B1;,
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Thiomorpholine 1,1-dioxide, cas is 39093-93-1, it is a common heterocyclic compound, the Thiomorpholine compound, its synthesis route is as follows.

Example 24 {6-[3-(3-?1iota1thetaGammatheta-rho1?6etagamma1)-5^6?1iotagamma1-?8thetaChi3zetaomicron1-4-gamma^6?1iotaomicronchigamma]-rhogammapi??eta-3-gamma1}-(1,1-??omicronchiomicron-1lambda6- thiomorpholin-4-yl)-methanone To a solution of 6-[3-(3-chloro-phenyl)-5-methyl-isoxazol-4-ylmethoxy]-nicotinic acid (69 mg, 0.2 mmol) in DMF (300 L) were added 2-(lH-benzotriazole-l-yl)-l, 1,3,3- tetramethyluronium tetrafluoroborate (71 mg, 0.22 mmol), Nu,Nu-diisopropyl ethyl amine (171 muL, 1.0 mmol) and thiomorpholine-S,S-dioxide (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 (80 mg, 87percent) which was obtained as a white solid. MS: m/e = 462.1 [M+H]+., 39093-93-1

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Patent; F. HOFFMANN-LA ROCHE AG; DOTT, Pascal; HANLON, Steven Paul; HILDBRAND, Stefan; IDING, Hans; THOMAS, Andrew; WALDMEIER, Pius; WO2013/57123; (2013); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.39093-93-1,Thiomorpholine 1,1-dioxide,as a common compound, the synthetic route is as follows.,39093-93-1

General procedure: To a vial containing a solution of urea acid, 8a, (369.7 mg, 1 mmol), EDCI (230.8 mg, 1.2 mmol) and HOBt (147.6 mg, 1.1 mmol) in 1:1 DCM:N,N-dimethylformamide (DMF; 10 mL) was added 1,1-dioxothiomorpholine (133.1 mg, 1 mmol). The vial was capped, and the solution was stirred at room temperature for 27 h. The reaction mixture was diluted with EtOAc and washed with water (x3) and brine (x1). The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under vacuum. Purification by silica flash column using 97:3 DCM:MeOH gave 401.0 mg (82percent) of 13a as a white solid. 1H NMR (400 MHz, acetone-d6): delta 10.03 (s, 1H), 9.23 (s, 1H), 8.11 (d, J = 8.4 Hz, 1H), 8.00 (d, J = 7.2 Hz, 1H), 7.86 (d, J = 8.0 Hz, 1H), 7.67 (d, J = 8.2 Hz, 1H), 7.49-7.41 (m, 2H), 7.40-7.34 (m, 1H), 6.70 (s, 1H), 4.14-4.05 (m, 4H), 3.20 (t, J = 4.8 Hz, 4H), 1.30 (s, 9H). MS m/z (APCI+) Found (M+H): 486.2

As the paragraph descriping shows that 39093-93-1 is playing an increasingly important role.

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Article; Moffett, Kristofer; Konteatis, Zenon; Nguyen, Duyan; Shetty, Rupa; Ludington, Jennifer; Fujimoto, Ted; Lee, Kyoung-Jin; Chai, Xiaomei; Namboodiri, Haridasan; Karpusas, Michael; Dorsey, Bruce; Guarnieri, Frank; Bukhtiyarova, Marina; Springman, Eric; Michelotti, Enrique; Bioorganic and Medicinal Chemistry Letters; vol. 21; 23; (2011); p. 7155 – 7165;,
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39093-93-1, Thiomorpholine 1,1-dioxide is a Thiomorpholine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,39093-93-1

(S)-3-Bromo-7-chloro-5-(phenyl(tetrahydro-2H-pyran-4-yl)methyl)-5H- pyrrolo[2,3-b:4,5-b’]dipyridine (150 mg, 0.328 mmol), thiomorpholine 1,1-dioxide (311 mg, 2.30 mmol) and the triethylamine (0.365 mL, 2.63 mmol) were dissolved in 1.2 mL of DMSO and microwaved at 175 ¡ãC for 2 h. It was diluted with 1percent MeOH/EtOAc and washed twice with brine. The organic layer was dried over MgS04 and concentrated to obtain 181 mg of crude. The crude material was purified via preparative LC/MS with the following conditions: Column: XBridge CI 8, 19 x 200 mm, 5-muiotatauiota particles; Mobile Phase A: 5:95 ACN: water with 10-mM NH4OAc; Mobile Phase B: 95:5 ACN: water with 10- mM NH4OAc; Gradient: 40-80percent B over 15 min, then a 5-min hold at 100percent B; Flow: 20 mL/min. Fractions containing the title compound were combined and dried via centrifugal evaporation. The yield of the product was 76percent. NMR (500MHz, DMSO- d6) delta 8.62 (br. s., 1H), 8.43 (s, 1H), 8.30 (d, J=8.4 Hz, 1H), 7.73 (d, J=7.3 Hz, 2H), 7.32 (t, J=7.5 Hz, 2H), 7.24 (t, J=7.3 Hz, 1H), 7.03 (d, J=8.8 Hz, 1H), 5.61 (br. s., 1H), 4.28 (br. s., 4H), 3.90 – 3.82 (m, 1H), 3.76 (d, J=10.3 Hz, 1H), 3.53 (br. s., 1H), 3.30 – 3.16 (m, 6H), 1.50 – 1.38 (m, 2H), 1.24 (d, J=7.3 Hz, 1H), 1.13 (d, J=l 1.0 Hz, 1H); LC/MS (M+H) = 555.0 [Column: Waters Aquity BEH C18 2.1 X 50 mm 1.7u; Mobile Phase A: water with 0.05percent TFA; Mobile Phase B: ACN with 0.05percent TFA; Temperature: 40 ¡ãC; Gradient: 2-98percent B over 1.5 min; Flow: 0.8 mL/min].

The synthetic route of 39093-93-1 has been constantly updated, and we look forward to future research findings.

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Patent; BRISTOL-MYERS SQUIBB COMPANY; NORRIS, Derek J.; VACCARO, Wayne; DEBENEDETTO, Mikkel V.; DEGNAN, Andrew P.; DELUCCA, George V.; DESKUS, Jeffrey A.; HAN, Wen-Ching; KUMI, Godwin Kwame; SCHMITZ, William D.; STARRETT, John E., JR.; HILL, Matthew D.; HUANG, Hong; (563 pag.)WO2016/183118; (2016); A1;,
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