Tag: M.W=100-200

Application of 16066-84-5,Some common heterocyclic compound, 16066-84-5, name is tert-Butyl methylcarbamate, molecular formula is C6H13NO2, 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.

General procedure: JohnPhos (22 mg, 0.075 mmol), NaO’Bu (54 mg, 0.564 mmol), Pd2(dba)3(69 mg, 0.075 mmol), and then pyrrolidin-3-ol (49 mg, 0.564 mmol) were added to a solution of Compound 4 (200 mg, 0.376 mmol) and dioxane (5 mL). The mixture was degassed with vacuum/N2 cycles (3chi), stirred at 100 C overnight, filtered, and then concentrated. The residue was purified by RP-HPLC (H20 (100 mM H4HC03)/ACN) to give Compound 6 (58 mg, 29%) as a white solid. 1H NMR (400 MHz, DMSO-i): delta 8.13 (d, 1H), 7.39-7.75 (m, 6H), 7.31 (d, 2H), 7.07 (d, 1H), 6.95-6.99 (m, 1H), 6.72 (s, 1H), 5.08 (d, 1H), 5.02 (d, 1H), 4.79 (d, 1H), 4.43 (d, 1H), 3.80 (s, 3H), 3.47-3.55 (m, 1H), 3.43 (d, 2H), 3.21-3.25 (m, 1H), 2.18 (s, 3H), 1.95-2.10 (m, 1H), 1.90-2.10 (m, 1H), 1.73-1.85 (m, 2H), 0.80 (s, 9H); MS: 538.4 [M+H]+.

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

Reference:
Patent; METACRINE, INC.; SMITH, Nicholas D.; GOVEK, Steven P.; NAGASAWA, Johnny Y.; (167 pag.)WO2018/170167; (2018); A1;,
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Reference of 326-67-0, 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 326-67-0 as follows.

Chlorosulfonic acid (20.56 g, 176.46 mmol, 5 equiv.) was slowly added to N-(2-fluoro-4-methylphenyl) acetamide (5.90 g,35.29 mmol, 1 equiv.) keeping the temperature of the reactionmixture below 50 C. The resulting mixture was then heated to70 C for 4 hours. After cooling to room temperature, thereaction mixture was then poured carefully into ice, the precipitate was filtered, washed well with distilled water and dried to get 7.3 g of crude product as light brown solid. The crude product thus obtained was further used as such without any purification.?H NMR (CDC13) : 6 9.09 (d, J = 7.6 Hz, 1H), 7.48 (bs, 1H), 7.14 (d, J = 10.8 Hz, 1H) , 2.72 (s, 3H) , 2.25 (s, 3H)

According to the analysis of related databases, 326-67-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; INSECTICIDES (INDIA) LIMITED; OAT AGRIO CO., LTD; IMAI, Tetsuya; KUMAWAT, Surendra Kumar; SINGH, Manish Kumar; CHAUHAN, Pramod Kumar; SHELKE, Amol Vasant; SINGH, Rajesh Kumar; KISHORE, Ram; BHATT, Ashish; (97 pag.)WO2018/15852; (2018); A1;,
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Reference of 19962-04-0, 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 19962-04-0 as follows.

General procedure: To a suspension of carboxylic acid (100mg) and DMAP (6 eq) in DCM (0.2 M) under nitrogen at -15C was added T3P (3 eq)dropwise over a period of 20 min. The resulting mixture was stirred at -15Cuntil a solution was obtained (2h) and the aniline (3 eq) was added dropwise.The reaction mixture was stirred at -15 C for 1h, slowly warmed to roomtemperature and stirred overnight. Saturated aq. NaHCO3 was thenadded and the aqueous layer extracted with EtOAc. The organic phase was washedwith saturated aq. NH4Cl (x 2), NaHCO3 and brine, driedover Na2SO4, filtered and concentrated under vacuum. Theresidue was dissolved in DCM and purified by flash chromatography (DCM/MeOH97/3 to 92/8).

According to the analysis of related databases, 19962-04-0, the application of this compound in the production field has become more and more popular.

Reference:
Article; Boland, Sandro; Bourin, Arnaud; Alen, Jo; Geraets, Jacques; Schroeders, Pieter; Castermans, Karolien; Kindt, Nele; Boumans, Nicki; Panitti, Laura; Vanormelingen, Jessica; Fransen, Silke; Van De Velde, Sarah; Defert, Olivier; Bioorganic and Medicinal Chemistry Letters; vol. 25; 18; (2015); p. 4005 – 4010;,
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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. 67442-07-3, name is 2-Chloro-N-methoxy-N-methylacetamide, A new synthetic method of this compound is introduced below., Recommanded Product: 2-Chloro-N-methoxy-N-methylacetamide

A mixture of (2-chloro-N-methoxy-N-methylacetamide (13.7 g, 0.1 mol) and triphenylphosphane (26.2 g, 0.1 mol) in acetonitrile (200 mL) was heated to 80 °C and held for 20 h. The mixture was cooled and concentrated to remove the solvent below 40 °C. The residue was dissolved in dichloromethane (200 mL), followed by 2 N KOH (100 mL). The resulting mixture was stirred at 20 °C for lh. Phase separation, the organic layer was washed with brine (200 mL*3), dried over Na2SO4 and filtered. The filtrate was concentrated in vacuum to afford N-methoxy-N-methyl-2-(triphenyl-15-phosphanylidene) acetamide (36 g, 0.1 mol, 98percent) as a yellow solid. ESI-MS (EI, m/z): 364.4 [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. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; NAVITOR PHARMACEUTICALS, INC.; SAIAH, Eddine; VLASUK, George; (239 pag.)WO2018/200625; (2018); A1;,
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Reference of 122848-57-1, 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. 122848-57-1, name is tert-Butyl 3,6-diazabicyclo[3.2.0]heptane-6-carboxylate, This compound has unique chemical properties. The synthetic route is as follows.

In a sealed tube, 7-fluoro-2-(2-methyl-[l,2,4]triazolo[l,5-a]pyrimidin-6-yl)-4H-pyrido[l,2- a]pyrimidin-4-one (Intermediate (VI-1), 25.4 mg, 0.169 mmol, 1 eq.), and tert-butyl 3,6- diazabicyclo[3.2.0]heptane-6-carboxylate (100 mg, 0.506 mmol, 3 eq.) were stirred in DMSO (2 ml) at 120C for 48 hours. The crude was purifed by preparative HPLC. (0364) The isolated solid was then treated following the General Procedure 1 for Boc deprotection to afford the product 7-(3,6-diazabicyclo[3.2.0]heptan-3-yl)-2-(2-methyl-[l,2,4]triazolo[l,5- a]pyrimidin-6-yl)-4H-pyrido[l,2-a]pyrimidin-4-one 2,2,2-trifluoroacetate (12.4 mg, 0.025 mmol, 73.9 % yield) as a yellow solid.

The chemical industry reduces the impact on the environment during synthesis tert-Butyl 3,6-diazabicyclo[3.2.0]heptane-6-carboxylate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; GILLESPIE, Robert Jack; HASANE, Ratni; SARIE, Jerome Charles; (89 pag.)WO2016/184832; (2016); A1;,
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Synthetic Route of 14433-76-2, The chemical industry reduces the impact on the environment during synthesis 14433-76-2, name is N,N-Dimethylcapramide, I believe this compound will play a more active role in future production and life.

Comparative example AIn the same reactor set up, example 1 is repeated except for the DMA addition. The selectivity towards N,N-dimethyldecylamine is reduced to 92.5 %, mainly at expense of N-methyldidecylamine and decanol.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, N,N-Dimethylcapramide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; TAMINCO; WO2006/136204; (2006); A1;,
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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. 17641-08-6, name is 2-Chloro-N-(3-methoxyphenyl)acetamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. name: 2-Chloro-N-(3-methoxyphenyl)acetamide

General procedure: To a stirred solution of substituted aniline (1 mmol) and chloroacetyl chloride (1 mmol) which was stirred in 5 mL DMF for 20 min, were added benzyl amine derivatives (1.3 mmol) and CS2 (5 mmol). The reaction mixture was allowed to stir for required additional time (Table 2). Then, 5 mL of water was added and the solution was extracted with ethyl acetate and dried over sodium sulfate and purified by passing over a silica gel column chromatography using petroleum ether/ethyl acetate (8:2).

The synthetic route of 17641-08-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Sadat-Ebrahimi, Seyed Esmail; Karim, Leila; Moghimi, Setareh; Yahya-Meymandi, Azadeh; Mahdavi, Mohammad; Vosooghi, Mohsen; Foroumadi, Alireza; Shafiee, Abbas; Journal of Sulfur Chemistry; vol. 38; 1; (2017); p. 43 – 51;,
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Some common heterocyclic compound, 1524-40-9, name is 3-Fluorobenzenesulfonamide, molecular formula is C6H6FNO2S, 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. COA of Formula: C6H6FNO2S

(1) 0.0040g iridium catalyst [Cp * IrCl2] 2,0.0076 g silver salt bis(trifluoromethanesulfonyl)imide silver,0.825g oxidant silver acetate,31.4muLacetophenone-O-methyl oxime and0.07 g of m-fluorobenzenesulfonamide was placed in a reaction tube.Add 2mL of dichloromethane as a solvent,Heating and stirring reaction,The temperature of heating and stirring is 60C.Reaction time 24h.(2) After the reaction is over,Separation by column chromatography (300-400 column chromatography silica gel column packing,Eluent: ethyl acetate: petroleum ether = 12:100 v/v),Can get the product N-[2-(1-Methoxyimino)ethyl]phenyl-3-fluorobenzenesulfonamide.The yield is 83%.The structural characterization of the products are shown in Figures 21 and 22, respectively.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1524-40-9, its application will become more common.

Reference:
Patent; University of Jinan; Zhao Huaiqing; Zhang Wei; Xu Xiangwen; Wu Wei; (40 pag.)CN107739322; (2018); A;,
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Related Products of 2439-77-2, These common heterocyclic compound, 2439-77-2, name is 2-Methoxybenzamide, 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.

Under argon, tert-butyl 4-(10-bromo-2-oxo-l,2-dihydropyrimido[l,2-b]indazol-4-yl)piperidine-l- carboxylate (200 mg, 447 muiotaetaomicron), 2-methoxybenzamide (169 mg, 1.12 mmol), Tripotassium phosphate (133 mg, 626 muiotaetaomicron), tBuBrettPhos (13.0 mg, 26.8 muiotaetaomicron), and tBuBrettPhos Pd G3 (22.9 mg, 26.8 muiotaetaomicron) were dissolved in l-Methoxy-2-propanol (5.0 ml, 52 mmol). The mixture was stirred at 110 C for 16 h and then purified via reverse phase chromatography (Method: Reprosil CI 8; 10 muiotaeta; 125×30 mm / flow: 50 ml/min / solvents: A = water (0,01% formic acid), B = Acetonitrile / gradient : 0.00-4.25 min = 20%B, 4.50min = 30%B, 19.00-22.50min = 100%B, 22.75-25.00min = 20%B) which afforded the product after drying in vacuo. The obtained amout was 130 mg (56 % of theory). LC-MS (Method 1): Rt = 1.15 min; MS (ESIpos): m/z = 518 [M+H]+

Statistics shows that 2-Methoxybenzamide is playing an increasingly important role. we look forward to future research findings about 2439-77-2.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; ELLERMANN, Manuel; VALOT, Gaelle; CANCHO GRANDE, Yolanda; HASSFELD, Jorma; KINZEL, Tom; KOeBBERLING, Johannes; BEYER, Kristin; ROeHRIG, Susanne; SPERZEL, Michael; STAMPFUSS, Jan; MEYER, Imke; KOeLLNBERGER, Maria; BURKHARDT, Nils; SCHLEMMER, Karl-Heinz; STEGMANN, Christian; SCHUHMACHER, Joachim; WERNER, Matthias; (308 pag.)WO2016/173948; (2016); A1;,
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Synthetic Route of 2360-20-5,Some common heterocyclic compound, 2360-20-5, name is 3,4-Diaminobenzenesulfonamide, molecular formula is C6H9N3O2S, 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.

General procedure: Benzaldehyde (73 muL, 0.72 mmol, 1 eq) was dissolved in EtOH (2-5 mL), and sodium metabisulfite (205 mg, 1.08 mmol, 1.5 eq) in H2O (1-2 mL) was added in dropwise. The reaction mixture was stirred at rt overnight. Reaction mixture was diluted with EtOH, cooled and formed precipitate was filtered and dried (128 mg). The mixture of this salt (124.6 mg, 0.596 mmol, 1.5 equiv) and 3-amino-4-(methylamino) benzenesulfonamide (3) (80 mg, 0.397 mmol, 1 equiv) in 5 mL DMF was heated at 60? for 6 h. Reaction mixture was diluted with water and formed precipitate was filtered. The crude product was purified by flash chromatography on silica gel (12 g), eluting with a gradient of 0-11% MeOH in DCM to give 4a (74.5 mg, 64.8% yield) as a white powder. Mp 266-268.6 C. 1H NMR (400 MHz, DMSO-d6): delta 3.92 (3H, s), 7.32 (2H, s), 7.58-7.60 (3H, m), 7.76-7.81 (2H, m), 7.85-7.88 (2H, m), 8.14 (1H, s); 13C NMR (100 MHz DMSO-d6): delta 32.05, 111.05, 116.93, 119.93, 128.75, 129.41, 129.48, 130.12, 138.25, 138.45, 141.53, 155.41; HRMS m/z calculated for C14H13N3O2S [M+H]+ 288.0807, found: 288.0794.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3,4-Diaminobenzenesulfonamide, its application will become more common.

Reference:
Article; Cal??kan, Burcu; Banoglu, Erden; Guer Maz, Tu?ce; Nocentini, Alessio; Supuran, Claudiu T.; Uslu, Azize Gizem; Bioorganic Chemistry; vol. 95; (2020);,
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