Amides-buliding-blocks

Adding a certain compound to certain chemical reactions, such as: 35303-76-5, name is 4-(2-Aminoethyl)benzenesulfonamide, 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 35303-76-5, HPLC of Formula: C8H12N2O2S

General procedure: Starting dichlorotriazinyl benzenesulfonamide (1 mmol; 0.320 g of4- [(4,6-dichloro-1,3,5-triazin-2-yl)amino]benzene-1-sulfonamide, 0.334 g of4-{[(4,6-dichloro-1,3,5-triazin-2-yl)amino]methyl}benzene-1-sulfonamide or 0.348 g of4-{2-[(4,6-dichloro-1,3,5-triazin-2-yl)amino]-ethyl}benzene-1-sulfonamide)) was dissolved in20 mL of DMF. Then 1 mmol (0.138 g) of solid anhydrous potassium carbonate was added in smallportions and the mixture was stirred for 10 min. Then 1 mmol of the appropriate nucleophile wasadded portion wise. Finally, 2.5% mol. of supported Cu(I) ions (312 mg of catalyst) was addedinto the reaction mixture. Reaction was stirred at 35 C until the maximum conversion of startingmaterial is achieved (monitored by TLC). After completion of the first reaction step, 1 mmol of thesecond nucleophile and 1 mmol (0.138 g) of anhydrous potassium carbonate were added into thereaction mixture. The reaction mixture was then stirred at 100 C until the maximum conversion of anucleophile was determined (monitored by TLC). After completion of a reaction, the catalyst andsalt were filtered o. Crushed ice was then added into the solution and the formed precipitate wascollected by filtration. The crude product was dissolved in acetone and precipitated by the addition ofisopropyl alcohol.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-(2-Aminoethyl)benzenesulfonamide, and friends who are interested can also refer to it.

Reference:
Article; Havrankova, Eva; Csoellei, Jozef; Pazdera, Pavel; Molecules; vol. 24; 19; (2019);,
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Synthetic Route of 33545-97-0, A common heterocyclic compound, 33545-97-0, name is N,N’-Di-Boc-1,4-butanediamine, molecular formula is C14H28N2O4, 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.

Commercially available putrescine 1 is (bis)-N-Boc protected to produce compound 2 (85.2% yield). Compound 2 is used to alkylate qty. 2 equivalents of propargyl bromide in the presence of sodium hydride producing compound 3 (59.5% yield). Yields in that transformation are further enhanced by using a mixture of dimethylformamide (“DMF”) and tetrahydrofuran (“THF”) in a ratio of 1:5. The propargyl groups in compound 3 are converted to the corresponding allenes in the presence of CuBr, formaldehyde, and diisopropylamine to yield intermediate compound 4 (38.7% yield). Compound 4 is de-protected in the presence of HCl to yield the desired target molecule MDL 72,527 (white solid, 65.8% yield). [00097] HPLC method of quantitation of MDL, natural polyamines and their acetyl derivatives in cell extracts as well as in human and animal serum is standardized. Therefore, the pharmacokinetics and pharmocodynamics of MDL 72,527 may be determined.

The synthetic route of 33545-97-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; WISCONSIN ALUMNI RESEARCH FOUNDATION; WO2007/130589; (2007); A2;,
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Electric Literature of 122334-37-6,Some common heterocyclic compound, 122334-37-6, name is 4-Chloro-N-methoxy-N-methylbenzamide, molecular formula is C9H10ClNO2, 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.

Ethyl magnesium bromide (3.0 M in diethyl ether, 21.5 mL, 64.4 mmol) was added via syringe over a few minutes to a clear colorless solution of 5-bromo-1-methyl-1H-imidazole (10.4 g, 64.4 mmol) in THF (100 mL) under a nitrogen atmosphere in an ice bath. A white precipitate formed during the addition. The mixture was removed from the ice bath and was stirred for 20 minutes, then was again cooled in an ice bath before addition of 4-chloro-N-methoxy-N-methylbenzamide (10.7 g, 53.6 mmol, Intermediate 43: step a). The resulting white suspension was stirred overnight at room temperature. The reaction was quenched by addition of saturated aqueous NH4Cl and diluted with water. The mixture was partially concentrated to remove THF and was diluted with DCM. The mixture was acidified to pH 1 with 1 N aqueous HCl, then neutralized with saturated aqueous NaHCO3. The phases were separated and the aqueous phase was further extracted with DCM. The organic extracts were washed with water, then were dried (Na2SO4), filtered, and concentrated, affording a white solid. The crude product was triturated with a mixture of EtOAc:heptanes (1:1, 150 mL). The precipitated solid was collected by vacuum filtration, washing with heptanes, to afford the title compound.

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

Reference:
Patent; Janssen Pharmaceutica NV; Leonard, Kristi A.; Barbay, Kent; Edwards, James P.; Kreutter, Kevin D.; Kummer, David A.; Maharoof, Umar; Nishimura, Rachel; Urbanski, Maud; Venkatesan, Hariharan; Wang, Aihua; Wolin, Ronald L.; Woods, Craig R.; Fourie, Anne; Xue, Xiaohua; Cummings, Maxwell D.; Jones, William Moore; Goldberg, Steven; US2015/105366; (2015); A1;,
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These common heterocyclic compound, 366-49-4, name is 2-Acetamido-4-fluorotoluene, 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. Application In Synthesis of 2-Acetamido-4-fluorotoluene

To a stirred solution of DMF (3 mL) at 00C was added phosphorus oxychloride (12 mL, 126 mmol) over 30 minutes, keeping the internal temperature below 7C. N-(5- Fluoro-2-methylphenyl)acetamide (2 g, 12 mmol) was added to the solution and heated to 85C overnight. The reaction was cooled to room temperature and added dropwise to water (50 mL). The precipitate was collected by filtration, washed with water and dried in the vacuum oven to give the title compound (274 mg, 10%) as a yellow solid. 5H (CDCl3) 10.58 (s, IH), 9.01 (s, IH), 7.60-7.70 (m, IH), 7.15-7.25 (m, IH), 2.75 (s, 3H).

The synthetic route of 2-Acetamido-4-fluorotoluene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UCB PHARMA S.A.; WO2009/81105; (2009); A2;,
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Some common heterocyclic compound, 120157-97-3, name is N-Boc-2-(4-Bromophenyl)ethylamine, molecular formula is C13H18BrNO2, 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. category: amides-buliding-blocks

(0937) [00331] Into a 100-mL round-bottom flask, purged and maintained under an inert atmosphere of nitrogen, was added fe/t~buty (4~bromophenethyl)carbarnate (4.00 g, 13.3 mmol) dissolved in anhydrous toluene (50-mL). To the resulting solution was added benzyl piperazine-1- carboxylate (3.53 g, 16.0 mmol), Pd(OAc)2 (0.300 g, 1.34 mmol), XPhos (1.28 g, 2.69 mmol), and CS2CO3 (13.1 g, 40.0 mmol). The reaction mixture was stirred overnight at 105 C in an oil bath and then cooled to RT and quenched with H2O (200 mL). The resulting mixture was extracted with ethyl acetate (2 x 50 mL). The combined organic layers were washed with brine (1 x 200 mL), dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The resulting crude product was purified by FCC eluting with ethyl acetate/petroleum ether (PE/EA=3: 1) to afford benzyl 4-(4-(2-((feri-butoxycarbonyl)amino)ethyl)phenyl) piperazine-1- carboxylate as a yellow solid (5 g, 85%), LCMS (ESI, m/z): 440 [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 120157-97-3, its application will become more common.

Reference:
Patent; FORMA THERAPEUTICS, INC.; GUERIN, David Joseph; BAIR, Kenneth W.; CARAVELLA, Justin A.; IOANNIDIS, Stephanos; LANCIA JR., David R.; LI, Hongbin; MISCHKE, Steven; NG, Pui Yee; RICHARD, David; SCHILLER, Shawn E. R.; SHELEKHIN, Tatiana; WANG, Zhongguo; (365 pag.)WO2017/139778; (2017); A1;,
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Reference of 35303-76-5, 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 35303-76-5 as follows.

4-(2-aminoethyl)benzenesulfonamide (0.86 mmol) was added to a THF solution (20 ml) of 1- (3-isocyanatopropyl) -4-methoxybenzene Gt; min. & Lt; / RTI & gt; The reaction mixture was stirred at 40-45¡ã C for 24 hours. The next day, TLC was used to confirm the termination of the reaction. The solvent was distilled off and ammonium chloride (100 ml), 1N HCl solution (50 ml) and ethyl acetate (100 ml) were added to the remaining residue. The organic layer was washed with brine and dried over sodium sulfate. The solvent was distilled off and the residue was adsorbed onto silica gel using methylene chloride. The title compound was then separated and purified by column chromatography using ethyl acetate and hexane

According to the analysis of related databases, 35303-76-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CHUNGNAM NATIONAL UNIVERSITY INDUSTRY & ACADEMIC COOPERATION (IAC); JUNG, SANG HUN; WOO, SUN HEE; KIM, SANG KYUM; JEON, EUN SEOK; LEE, YOU JUNG; MANICKAM, MANOJ; JALANI HITESHKUMAR, HITESHKUMAR; SHARMA, NITI; (234 pag.)KR2015/111825; (2015); A;,
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Adding a certain compound to certain chemical reactions, such as: 119023-25-5, name is 2-Amino-4-fluorobenzamide, 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 119023-25-5, Product Details of 119023-25-5

[00304] Step A: To a solution of 2-bromo-2-(4-fluorophenyl)acetic acid (425 mg, 1.82 mmol) in DCM (5 mL) and DMF (0.05 mL) was added oxalyl chloride (0.17 mL, 1.91 mmol) and the solution was stirred for 0.75 h. The solution was then cooled to 0 oC and a solution of 2-amino-4-fluorobenzamide (267 mg, 1.73 mmol) in pyridine (1 mL) was added. The solution was stirred at rt for 1 h and then evaporated. The crude residue was partitioned between EtOAc and 2 N HCl. The EtOAc layer was evaporated to give 2-(2-bromo-2-(4-fluorophenyl)acetamido)-4-fluorobenzamide as a crude oil which was used without further purification. (420 mg, 62%). LC-MS (ESI) m/z 369 (M – H)-.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; AMBIT BIOSCIENCES CORPORATION; LIU, Gang; CHAO, Qi; HADD, Michael, J.; HOLLADAY, Mark, W.; ABRAHAM, Sunny; SETTI, Eduardo; WO2010/99379; (2010); A1;,
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Electric Literature of 478837-18-2, 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. 478837-18-2 name is tert-Butyl 3-hydroxy-8-azabicyclo[3.2.1]octane-8-carboxylate, 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.

To a solution of tert-butyl 3-hydroxy-8-azabicyclo [3.2.1] octane-8-carboxylate (2 g, 8.80 mmol) and triethylamine (1.84 mL, 13.20 mmol) in dichloromethane (10 mL) Was added and stirred at 0 C, methanesulfonyl chloride (0.817 mL, 10.56 mmol) was added and reacted for 2 hours. The solvent was removed from the resulting mixture under reduced pressure, and the reaction mixture was extracted with dichloromethane (40 mL), dried using anhydrous magnesium sulfate, filtered and the solvent was removed under reduced pressure. The obtained organic layer was purified by silica gel flash column chromatography (ethyl acetate: hexane = 1: 4) to obtain tert-butyl 3- (methylsulfonyloxy) -8-azabicyclo [3.2.1] octane-8-carboxylate 92.4%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, tert-Butyl 3-hydroxy-8-azabicyclo[3.2.1]octane-8-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; KOREA INSTITUTE OF SCIENCE AND TECHNOLOGY; NOH, Eun Joo; SIM, Tae Bo; AHN, Dae Ro; CHOI, Seung Ho; (25 pag.)KR101683061; (2016); B1;,
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Application of 56987-35-0, These common heterocyclic compound, 56987-35-0, name is 3,3-Dibromo-azepan-2-one, 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.

A solution of 3,3-dibromoazepan-2-one (15.7 g, 57.9 mmol) in piperidine (140 mL) was heated at reflux for 4.5 h under N2. The solution was then allowed to reach room temperature and washed with 0.50 M aq. NaHS03 (200 mL). The aqueous phase was extracted with CHC13 (3 x 100 mL) and the combined organic layers were washed with brine (1 x 300 mL), dried (MgS04) and concentrated to afford a brown, oily solid, that crystallized upon standing. The resulting solid was suspended in water, filtered, and washed with water and Et20 to give 1 (10.3 g, 91%) as a white solid: IR (ATR, neat) 3193, 2950, 2935, 2923, 2855, 1655, 1605 cm”1; 1H NMR (CDC13, 600 MHz) delta 6.51 (bs, 1 H), 5.06 (t, 1 H, J= 7.6 Hz), 3.22 (q, 2 H, J= 6.5 Hz), 2.78 (app t, 4 H, J= 5.3 Hz), 2.15 (q, 2 H, J= 7.2 Hz), 1.76 (app quint, 2 H, J= 6.8 Hz), 1.69-1.62 (m, 4 H), 1.54-1.48 (m, 2 H); 13C NMR (CDC13, 150 MHz) delta 171.5, 147.6, 105.4, 50.1, 39.5, 30.2, 25.5, 24.5, 21.5; HRMS (EI) m/z calcd for CiiH18N20 194.1419, found 194.1422.

Statistics shows that 3,3-Dibromo-azepan-2-one is playing an increasingly important role. we look forward to future research findings about 56987-35-0.

Reference:
Patent; UNIVERSITY OF PITTSBURGH – OF THE COMMONWEALTH SYSTEM OF HIGHER EDUCATION; WIPF, Peter; WANG, Qiming, Jan; WO2012/78859; (2012); A2;,
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Reference of 627-12-3, 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. 627-12-3, name is Propyl carbamate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: CuI (10mol%) and EDA (10mol%) were added to a mixtureof O-alkyl carbamate (1mmol), NaOtBu (1.5mmol) and aryl halide (1mmol) in 2mL toluene and the mixture wasstirred for the appropriate time, which was determined byTLC monitoring, at 100C. After completion of the reaction,the catalyst was removed by filtration and 20mL H2Owas added to the filtrate. The resultant mixture was extractedwith CHCl3.Then the organic phase was washed with water(2 ¡Á 10mL) and dried over anhydrous Na2SO4.After evaporationof CHCl3under reduced pressure, the correspondingcrude product was purified by flash chromatography to givethe desired pure cross-coupling product in good to excellentyield. In the case of using arylboronic acids as couplingpartners, Cu(OAc)2 was employed instead of CuI.

The synthetic route of Propyl carbamate has been constantly updated, and we look forward to future research findings.

Reference:
Article; Sardarian, Ali Reza; DindarlooInaloo, Iman; Zangiabadi, Milad; Catalysis Letters; vol. 148; 2; (2018); p. 642 – 652;,
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