Tag: M.W=200-300

In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 16091-26-2 as follows. Product Details of 16091-26-2

(c) N-(3-((7-Chloro-5-hydroxy-1 ,1 -dioxido-2H-benzo[e][1 ,2,4]thiadiazin-3- yl)amino)phenyl)benzamide To a solution of 3-bromo-7-chloro-5-hydroxy-4H-benzo[e][1 ,2,4]thiadiazine 1 ,1 -dioxide (lnt-3, 200 mg) in t-BuOH (10 mL) was added KH2P04 (105 mg) at RT followed by N-(3- aminophenyl)benzamide (164 mg). The reaction mixture was stirred at 1 10 C for 16 hr. The reaction mixture was allowed to cool to RT and then quenched with water. The resulting precipitate was collected by filtration, washed with water, and dried under vacuum to afford the titled compound (158 mg). LCMS m/z 443.02 (M+H). 1H NMR after D20 exchange (400 MHz, DMSO-c/e) delta ppm 7.10 (d, J=2.19 Hz, 1 H) 7.20 (d, J=2.19 Hz, 1 H) 7.34 – 7.46 (m, 2 H) 7.48 – 7.64 (m, 4 H) 7.85 – 8.10 (m, 3 H).

According to the analysis of related databases, 16091-26-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; ADAMS, Jerry Leroy; ATOR, Laura E.; DUFFY, Kevin J.; GRAYBILL, Todd L.; KIESOW, Terence John; LIAN, Yiqian; MOORE, Michael Lee; RALPH, Jeffrey M.; RIDGERS, Lance Howard; (370 pag.)WO2017/98421; (2017); A1;,
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1103234-56-5, The chemical industry reduces the impact on the environment during synthesis 1103234-56-5, name is 2,6-Difluoro-3-(propylsulfonamido)benzoic acid, I believe this compound will play a more active role in future production and life.

2,6-Difluoro-3-(propylsulfonamido)benzoic acid (20.O g, 71.6 mmol) was dissolved in acetone (400 mL), and potassium carbonate (29.7 g, 215 mmol) was added. After stirring for 5 minutes, methyl iodide (13.4 mL, 215 mmol) was added. The reaction mixture was stirred overnight. The reaction mixture was filtered and the filtrate concentrated. The crude product was partitioned between ethyl acetate and water and the organic layer washed by brine, dried over MgSO4 and concentrated to dryness. Further removal of solvent under high vacuum afforded methyl 2,6-difluoro-3-(N-methylpropylsulfonamido)benzoate as light yellow solid (17.0 g, 77% yield). 1H NMR (500 MHz, CDCl3) delta 7.57 (td, IH), 7.10 – 6.89 (m, IH), 3.96 (s, 3H), 3.31 (s, 3H), 3.13 – 2.96 (m, 2H), 2.01 – 1.81 (m, 2H), 1.07 (t, 3H).

The chemical industry reduces the impact on the environment during synthesis 2,6-Difluoro-3-(propylsulfonamido)benzoic acid. I believe this compound will play a more active role in future production and life.

Reference:
Patent; ARRAY BIOPHARMA INC.; GENENTECH, INC.; ALIAGAS, Ignacio; GRADL, Stefan; GUNZNER, Janet; MATHIEU, Simon; RUDOLPH, Joachim; WEN, Zhaoyang; WENGLOWSKY, Steven Mark; WO2011/25947; (2011); A1;,
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Electric Literature of 202207-79-2,Some common heterocyclic compound, 202207-79-2, name is 1-(Boc-amino)-2-(methylamino)ethane Hydrochloride, molecular formula is C8H19ClN2O2, 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.

Step 1: tert-Butyl 2-(1-benzyl-3-(4-chlorophenyl)-N,4-dimethyl-5-(trifluoromethyl)-1H-pyrrole-carboxamido)ethylcarbamate ACI-03 (500 mg, 1.27 mmol) and tert-butyl 2-(methylamino)ethylcarbamate HCl (401 mg, 1.905 mmol) were dissolved in DME (2 mL) and BOP-CI (679 mg, 2.67 mmol) and DIPEA (0.929 mL, 5.33 mmol) were added. The reaction mixture was stirred at 60 C. for 1.5 h and then cooled to room temperature. Saturated aqueous NaHCO3 and EtOAc were added. The aqueous layer was extracted with EtOAc, the organic layers were combined, dried (Na2SO4) and evaporated. The product was purified by flash column chromatography (silica, gradient heptane/EtOAc, 1:0?3:1) to afford 587 mg (84%) of the desired product.

The synthetic route of 202207-79-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SCHUNK, Stefan; REICH, Melanie; STEINHAGEN, Henning; DAMANN, Nils; HAURAND, Michael; KLESS, Achim; SKONE, Philip; HAMLYN, Richard; KIRBY, Robert; ROGERS, Marc; SUTTON, Kathy; US2014/66426; (2014); A1;,
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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. 16313-66-9, name is 2-Amino-5-bromobenzamide, This compound has unique chemical properties. The synthetic route is as follows., category: amides-buliding-blocks

12468] To a solution of compound 69-2 (22.0 g, crude product) in dry THF (250 mE), compound 69-5 (7.6 g, 35.5 mmol) and 1M NaOH (aq. 85 mE, 85 mmol) were added in turn. At the end of addition, the mixture was stirred at rt for 1 hr. After the reaction was completed, the mixture was extracted with EtOAc (100 mEx3). The combined organic layers were washed with 1M NaOH aqueous solution (15.0 mE) and brine, dried over Na2504 and concentrated in vacuo to give the title compound 6 9-6. The compound was characterized by the following spectroscopic data:12469] MS (ESI, pos.ion) mlz: 446.5 [M+H]12470] ?H NMR (400 MHz, CDC13) oe (ppm): 9.06 (br, 1H),7.75 (d, 1H), 7.35, 7.33 (d, d, 1H), 7.28-7.22 (m, 5H), 6.69,6.67 (d, d, 1H), 5.68 (brs, 2H), 5.14-5.13 (m, 2H), 4.29-4.25 (m, 1H), 3.66-3.60 (m, 1H), 3.45-3.37 (m, 1H), 2.39-2.32 (m, 1H), 2.09-2.00 (m, 1H), 1.96-1.77 (m, 2H).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 16313-66-9.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD; Zhang, Yingjun; Zhang, Jaincun; Xie, Hongming; Ren, Qingyun; Tan, Yumei; Luo, Huichao; US2015/79028; (2015); A1;,
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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. 456-64-4, name is 1,1,1-Trifluoro-N-phenylmethanesulfonamide, This compound has unique chemical properties. The synthetic route is as follows., category: amides-buliding-blocks

6-Oxo-6,7-dihydro-thieno[2,3-b]pyridine-5-carboxylic acid methyl ester described in Preparation Example T-8 (9mg, 43mumol), N-phenyltrifluoromethanesulfonimide (23mg, 65mumol) and dimethyl-pyridin-4-yl-amine (catalytic amount) were dissolved in dichloromethane (0.5mL), and the solution was stirred for 18.5 hours at room temperature. Water was added to the reaction solution, which was then extracted with ethyl acetate, the organic layer was washed with brine and dried over anhydrous magnesium sulfate. The solvent was evaporated in vacuo, the residue was purified by NH silica gel column chromatography (hexane : ethyl acetate = 3 : 1), and the title compound (10mg, 29mumol, 68%) was obtained as a white solid. 1H-NMR Spectrum (CDCl3) delta(ppm) : 4.03 (3H, s), 7.43 (1H, d, J=5.9Hz), 7.73 (1H, d, J=5.9Hz), 8.87 (1H, s).

According to the analysis of related databases, 456-64-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Eisai Co., Ltd.; EP1669348; (2006); A1;,
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Application of 143557-91-9, A common heterocyclic compound, 143557-91-9, name is tert-Butyl 3-endo-3-hydroxy-8-azabicyclo[3.2.1]octane-8-carboxylate, molecular formula is C12H21NO3, 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.

To a solution of tert-butyl (3-endo)-3-hyd roxy-8-azabicyclo[3.2.1 ]octane-8-carboxylate (3g, 13.20 mmol, combi-blocks) in THF (30 mL) was added portion wise potassium tertbutoxide (1.6 g, 14.5 mmol). The reaction was then refluxed for lh. The reaction was removed from the oil bath and 1-bromo-2,4-difluoro-benzene (1.6 mL, 14.52 mmol, Matrix) was added. The reaction was again refluxed for 1 .5h and cooled to RT. Ethyl acetate was added. The layers were separated and the organic layer was washed withwater, brine, dried over sodium sulphate, filtered and concentrated in vacuo. The crude was purified by flash chromatography using 5% ethyl acetate in cyclohexane to give a colourless oil that crystallised upon standing (4.1 g, 79%). 1H NMR (400 MHz, DMSOd 6): 67.63-7.59 (m, 1H), 6.98 (dd, J1= 11.40, J2= 2.76 Hz, 1H), 6.76-6.71 (m, 1H), 4.81 (t, J= 4.40 Hz, 1H), 4.06 (s, 2H), 2.15-2.05 (m, 4H), 1.87-1.84 (m, 4H), 1.41 (s, 9H).LCMS: (Method A) 344.0 (M-?Bu-f-H), Rt. 6.2 mm, 84.9% (Max).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; ASCENEURON SA; QUATTROPANI, Anna; KULKARNI, Santosh S.; MURUGESAN, Kathiravan; BANERJEE, Joydeep; WO2014/198808; (2014); A1;,
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Some common heterocyclic compound, 123986-64-1, name is tert-Butyl 4-(hydroxymethyl)benzylcarbamate, molecular formula is C13H19NO3, 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. Recommanded Product: tert-Butyl 4-(hydroxymethyl)benzylcarbamate

Stage 3 – Preparation of te/t-butyl (4-formylbenzyl)carbamate; Stage 2 product (5.87g, 24.73mmol) was stirred in DCM (20OmL) with MnO2 (16.71g, 192.2mmol) for 16h at RT. The reaction was then filtered through celite and the solvent removed in vacuo to give the product as a yellow oil (4.63g, 80%). m/z = 258 [M+Na]

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 123986-64-1, its application will become more common.

Reference:
Patent; CHROMA THERAPEUTICS LTD.; WO2008/40934; (2008); A1;,
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Electric Literature of 42137-88-2,Some common heterocyclic compound, 42137-88-2, name is N,N-Bis(2-chloroethyl)-4-methylbenzenesulfonamide, molecular formula is C11H15Cl2NO2S, 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.

To a stirred solution of (R)-1-(benzo[d][1,3]dioxol-5-yl)ethan-1-amine (2 g, 12.1 mmol) in DIPEA (4.22 mL, 24.2 mmol), N,N-bis(2-chloroethyl)-p-toluene sulfonamide (3.9 g, 13.3 mmol) was added at rt and the resulting mixture was heated to 105 C for 18 h. Completion of the reaction was confirmed by TLC. Reaction mixture was diluted with water (30 mL) and extracted with EtOAc (2 x 50 mL). The combined organic layer was dried over Na2SO4 and evaporated under vacuum. To the resulting crude solid hexane (50 mL) was added, and the resulting mixture was stirred for 10 min at rt. It was filtered and the solid was washed with Et2O (2 x 50 mL) and dried under vacuum to give the title compound. Yield: 63.8% (3 g, off white solid). 1H NMR (400 MHz, DMSO-d6): delta 7.59 (d, J = 8.4 Hz, 2H), 7.45 (d, J = 8.0 Hz, 2H), 6.81-6.77 (m, 2H), 6.69-6.6 (m, 1H), 5.97-5.95 (m, 2H), 3.35-3.31 (m, 1H), 2.81-2.80 (m, 4H), 2.42 (s, 3H), 2.36-2.32 (m, 4H), 1.18 (d, J= 6.8 Hz, 3H). LCMS: (Method A) 389.0 (M+H), Rt. 3.39 min, 98.9% (Max). HPLC: (Method A) Rt. 3.30 min, 99.53% (Max), Chiral HPLC: (Method A) Rt. 15.54 min, 97.58%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route N,N-Bis(2-chloroethyl)-4-methylbenzenesulfonamide, its application will become more common.

Reference:
Patent; ASCENEURON SA; QUATTROPANI, Anna; KULKARNI, Santosh S.; GIRI, Awadut Gajendra; (243 pag.)WO2016/30443; (2016); A1;,
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In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 114790-39-5 as follows. Computed Properties of C12H17NO4

A solution of benzyl N-(2,2-dimethoxyethyl)carbamate (50 g, 208.9 mmol) in toluene (180 mL) is treated with solid potassium hydroxide (51.6 g, 919.69 mmol) under nitrogen. After 10 minutes, benzyltriethylammonium chloride (0.8 g, 3.1 mmol) is added. After another 10 minutes a solution of allyl bromide (33 g, 272.8 mmol) in toluene (50 mL) is added dropwise over 10 minutes. The resultant mixture is stirred at 50 C for 48hours. The mixture is cooled to room temperature and quenched with water. The organic layer is separated, washed with brine, dried over magnesium sulfate, and concentrated to dryness to give the title compound (44 g, 75%). ES/MS (mlz): 280 (M+H).

According to the analysis of related databases, 114790-39-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ELI LILLY AND COMPANY; COATES, David Andrew; WOLFANGEL, Craig Daniel; (55 pag.)WO2016/122968; (2016); A1;,
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Adding a certain compound to certain chemical reactions, such as: 127828-22-2, name is tert-Butyl (2-(2-aminoethoxy)ethyl)carbamate, belongs to amides-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 127828-22-2, COA of Formula: C9H20N2O3

A solution of 6-chloro-4-hydroxy-5-methyl-3-nitropyridin-2(iH)-one (10.9 g, 53.4 mmol) in dichloromethane (380 mL) was cooled to 0 C. Triethylamine (22.3 mL, 160 mmol) was added, and the solution was stirred for ten minutes. Trifluoromethanesulfonic anhydride (18.0 mL, 107 mmol) was then added dropwise over a period of five minutes, and the solution was stirred for 1.5 hours at 0 C. A solution of tert-butyl 2-(2-aminoethoxy)ethylcarbamate (12.0 g, 58.8 mmol), prepared as described in Parts A through D of Example 102, in a small amount of dichloromethane was then added over a period of five minutes, and the reaction was allowed to warm to room temperature slowly and stirred overnight. The solution was then washed with water (2×150 mL) and brine (150 mL), dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluting sequentially with 80:20 hexanes:ethyl acetate and 50:50 hexanes:ethyl acetate) to provide a yellow oil, which was dissolved in diethyl ether and concentrated under reduced pressure to provide 16.5 g of trifluoromethanesulfonic acid 4-[(2-{2-[(tert-butoxycarbonyl)amino]ethoxy}ethyl)amino]-6-chloro-5-methyl-3-nitropyridin-2-yl ester as a solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, tert-Butyl (2-(2-aminoethoxy)ethyl)carbamate, and friends who are interested can also refer to it.

Reference:
Patent; Dellaria, Joseph F.; Lindstrom, Kyle J.; Dressel, Luke T.; Duffy, Daniel E.; Heppner, Philip D.; Jacobsen, John R.; Moseman, Joan T.; Moser, William H.; Radmer, Matthew R.; Stoermer, Doris; Zimmermann, Bernhard M.; US2004/10007; (2004); A1;,
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