Category: amides-buliding-blocks

Reference of 480452-05-9,Some common heterocyclic compound, 480452-05-9, name is N-Boc-2-methyl-1,3-propanediamine, molecular formula is C9H20N2O2, 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) A solution of tert-butyl (3-amino-2-methylpropyl)carbamate (200 mg, 1.06 mmol), 4-cyanobenzoic acid (156 mg, 1.06 mmol), HATU (525 mg,1.38 mmol) and TEA (0.444 mL, 3.19 mmol) in DMF (5 mL) was stirred at room temperature for 16 hr. Water was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was dried, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (solvent gradient; 10 to 50% ethyl acetate/hexane) to give tert-butyl (3-(4-cyanobenzamido)-2-methylpropyl)carbamate (311 mg, 0.980 mmol, 92%) as a white powder. 1H-NMR(300MHz,CDCl3) :delta0.83(3H,d,J=6.8Hz), 1.37(9H,s), 1.74-1.93(1H,m), 2.76-3.00(2H,m), 3.05-3.25(2H,m), 6.82(1H,t,J=5.7Hz), 7.93-8.02(4H,m), 8.65(1H,t,J=5.5Hz)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route N-Boc-2-methyl-1,3-propanediamine, its application will become more common.

Reference:
Patent; Takeda Pharmaceutical Company Limited; YAMAMOTO, Satoshi; SHIRAI, Junya; FUKASE, Yoshiyuki; TOMATA, Yoshihide; SATO, Ayumu; OCHIDA, Atsuko; YONEMORI, Kazuko; NAKAGAWA, Hideyuki; EP2759533; (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. 96-72-0, name is 2-Chloro-5-nitrobenzenesulfonamide, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 96-72-0

An aqueous solution of NaOH (3.66 g; 92 mmol; 10% w/v) was added to a solution of 3-iodophenol (18.30 g; 83 mmol) in acetone (130 mL). Evaporation under reduced pressure afforded the crystals of the sodium salt 5, which were added to a solution of sulfonamide 4 (3.94 g; 17 mmol) in acetonitrile (24 mL). The mixture was refluxed and potassium carbonate (1.62 g; 12 mmol) was added. After completion of the reaction (48 h, monitored by TLC), the solution was acidified using 12M HCl, diluted with water and extracted with ethyl acetate (¡Á3). The combined organics were dried (MgSO4), and concentrated in vacuo. The crude product was purified using column chromatography (SiO2; pentane/ethyl acetate, 3:1), yielding the title compound 6 as a colorless solid (5.84 g; 84%). M.p. 153-155 C. (lit. 153-154 C.).

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 96-72-0.

Reference:
Patent; University College Dublin, National University of Ireland, Dublin; Kinsella, B. Therese; Reid, Helen; (104 pag.)US2016/102051; (2016); A1;,
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Synthetic Route of 1122-56-1, 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. 1122-56-1, name is Cyclohexanecarboxamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A mixture of cyclohexane carboxamide (1.1 g, 8.56 mmol) and Lawesson’s reagent (2.08 g, 5.14 mmol) in THF (35 mL) was stirred at 50 C. for 5 h. The reaction mixture was cooled, concentrated in vacuo, and purified by silica gel column chromatography (0-50% EtOAc in hexanes) to yield cyclohexane thioamide (938 mg, 77%).

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

Reference:
Patent; VICURON PHARMACEUTICALS INC.; US2006/211603; (2006); A1;,
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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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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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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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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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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. 79722-21-7, name is tert-Butyl benzyloxycarbamate, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 79722-21-7

General procedure: Nucleophile (1-3 mol equiv), tris-(dibenzylideneacetone)dipalladium (2.5 mol %), tris-(2-furyl)phosphine (10 mol %) and potassium carbonate (2 mol equiv) were added to a solution of the aryl halide (1 mmol) in dry dimethylformamide (10 mL) in a Schlenk tube. The reaction mixture was then degassed using the freeze, pump, thaw (F.P.T.) technique (one cycle). Allene gas was then introduced at the required pressure (1 atm) and the Schlenk tube contents stirred and heated at 80 C for 16 h. After cooling and venting, DCM (20 mL) was added and the mixture filtered to remove inorganic salts. The filtrate was concentrated in vacuo and the residue was purified by column chromatography.

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 79722-21-7.

Reference:
Article; Elboray, Elghareeb E.; Gao, Chuanjun; Grigg, Ronald; Tetrahedron; vol. 68; 14; (2012); p. 3103 – 3111;,
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Adding a certain compound to certain chemical reactions, such as: 38267-76-4, name is tert-Butyl ethylcarbamate, 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 38267-76-4, HPLC of Formula: C7H15NO2

[00753] Step F: 5-chloro-3-(4-(2-fluorophenoxy)cyclohex-1-en-1-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazolo[3,4-c]pyridine (0.75 g, 1.58 mmol) and tert-butyl ethylcarbamate (0.92 g, 6.33 mmol) were dissolved in dioxane (16 mL) and dicyclohexyl(2′,6′-diisopropoxy-[1,1′-biphenyl]-2-yl)phosphane (0.29 g, 0.63 mmol), sodium t-butoxide (0.30 g, 3.2 mmol) and Pd2dba3 (0.29 g, 0.32 mmol) were added and purged with nitrogen. The tube was sealed and heated to 100 C overnight, partitioned between EtOAc and water, extracted with EtOAc, dried over sodium sulfate, filtered and concentrated. The residue was purified over silica gel (10-30% EtOAc in hexanes) to afford tert-butyl ethyl(3-(4-(2-fluorophenoxy)cyclohex-1-en-1-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazolo[3,4-c]pyridin-5-yl)carbamate (615 mg, 66.7% yield).

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, tert-Butyl ethylcarbamate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ARRAY BIOPHARMA INC.; ALLEN, Shelley; BOYS, Mark Laurence; COOK, Adam; GAUDINO, John; HINKLIN, Ronald Jay; LAIRD, Ellen; MCNULTY, Oren T.; METCALF, Andrew T.; NEWHOUSE, Brad; ROBINSON, John E.; (545 pag.)WO2019/113190; (2019); A1;,
Amide – Wikipedia,
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98-64-6, name is 4-Chlorobenzenesulfonamide, belongs to amides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. category: amides-buliding-blocks

General procedure: To a mixture of PS-tet-Cu(II) 2 (0.05 g) and arylboronicacid (0.7 mmol) in water (5 mL), K2CO3(1 mmol), sulfonamide(0.7 mmol) and water (5 mL) was added and the mixture was vig-orously stirred for the appropriate times under reflux conditions.After completion (as monitored by TLC), the catalyst was filteredand the reaction mixture was cooled to room temperature. Theresulting product was filtered and purified by recrystallizationusing ethyl acetate and n-hexane to afford N-arylated product. Allcompounds were compared with the corresponding compoundsprepared by the reported procedure [4,23?40]. All compounds wereknown and were characterized by spectral analysis or meltingpoints.1H NMR data of some compounds are given below.

The synthetic route of 98-64-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Nasrollahzadeh, Mahmoud; Rostami-Vartooni, Akbar; Ehsani, Ali; Moghadam, Majid; Journal of Molecular Catalysis A: Chemical; vol. 387; (2014); p. 123 – 129;,
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