Tag: M.W=200-300

Electric Literature of 111300-06-2, 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. 111300-06-2 name is tert-Butyl (trans-4-hydroxycyclohexyl)carbamate, 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.

A solution of tert-butyl N-(4- hydroxycyclohexyl)carbamate (412 mg, 1.91 mmol, 1.10 equiv) in freshly distilled tetrahydrofuran (10 mL) was treated with sodium hydride (60% dispersion in mineral oil, 280 mg, 4.00 equiv) for 1 h at room temperature under nitrogen. To this mixture was then added a solution of 16.3 (510 mg, 1.72 mmol, 1.00 equiv) in dry tetrahydrofuran (5 mL) via syringe. After stirring overnight at room temperature, the reaction was then quenched with water and extracted with ethyl acetate (3 x 50 mL). The combined organic layers were washed with brine and dried over sodium sulfate. After filtration and concentration under reduced pressure, the residue was loaded onto a silica gel column with ethyl acetate/petroleum ether (1:2) and purified to afford ethyl 2-[(35)-12-[(4-[[(tert-butoxy)carbonyl]amino]cyclohexyl)oxy]-7-thia-9,l l- diazatricyclo[6.4.0.0A[2,6]]dodeca-l(12),2(6),8,10-tetraen-3-yl]acetate (16.4, 400 mg, 49%) as a yellow oil.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, tert-Butyl (trans-4-hydroxycyclohexyl)carbamate, and friends who are interested can also refer to it.

Reference:
Patent; NIMBUS IRIS, INC.; HARRIMAN, Geraldine, C.; WESTER, Ronald T.; ROMERO, Donna L.; ROBINSON, Shaughnessy; SHELLEY, Mee; WESSEL, Matthew David; GREENWOOD, Jeremy Robert; MASSE, Craig E.; KAPELLER-LIBERMANN, Rosana; WO2013/106535; (2013); A1;,
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Adding a certain compound to certain chemical reactions, such as: 42137-88-2, name is N,N-Bis(2-chloroethyl)-4-methylbenzenesulfonamide, 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 42137-88-2, Recommanded Product: N,N-Bis(2-chloroethyl)-4-methylbenzenesulfonamide

Alternatively, Intermediate 1 can be prepared from commercially available starting materials 5-iodo-methoxyaniline and N,N-bis(2-chloroethyl)-4-methylbenzenesulfonamide. Treatment of 5-iodo-methoxyaniline and N,N-bis(2-chloroethyl)-4-methylbenzenesulfonamide with sodium carbonate and potassium iodide in cyclohexanol at 160 C. will provide 1-(5-iodo-2-methoxyphenyl)-4-tosylpiperazine. Coupling of 1-(5-iodo-2-methoxyphenyl)-4-tosylpiperazine with sodium 3-(difluoromethoxy)benzenesulfinate can be accomplished by treatment with Xantphos, cesium carbonate, and tetrabutyl ammonium chloride. The resulting 1-(5-(3-(difluoromethoxy)phenylsulfonyl)-2-methoxyphenyl)-4-tosylpiperazine can be converted to Intermediate 1 by treatment with concentrated sulfuric acid at 50 C. for 5 hours.

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-Bis(2-chloroethyl)-4-methylbenzenesulfonamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Black, Lawrence A.; US2014/120036; (2014); A1;,
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Amide – an overview | ScienceDirect Topics

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. 138-41-0, name is Carzenide, A new synthetic method of this compound is introduced below., Safety of Carzenide

General procedure: To a stirred solution of the carboxylic acid (1.0 mmol) in anhydrous CH2Cl2 (5 mL), the appropriate amine or its hydrochloric acid(1 mmol), Et3N (1 eq, 0.14 mL, 1 mmol or 2 eq, 0.28 mL, 2 mmol in caseof hydrochloric acid), HOBt (1 eq, 140 mg, 1 mmol) and EDCI (1.1 eq,211 mg, 1.1 mmol) were added at 0 C. The reaction mixture was stirred overnight at room temperature and then the solvent was removedunder reduced pressure. The residue was dissolved in AcOEt and washedwith H2O, 5% H2SO4, H2O, 5% NaHCO3, brine and H2O. In thecase of proline washing with 5% H2SO4, was omitted. The product was obtained after drying the organic phase over anhydrous Na2SO4, evaporation of the solvent under reduced pressure, and purification by column chromatography.

The synthetic route of 138-41-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Afantitis, Antreas; Aidinis, Vassilis; Gerokonstantis, Dimitrios Triantafyllos; Kokotos, George; Magkrioti, Christiana; Moutevelis-Minakakis, Panagiota; Nikolaou, Aikaterini; Bioorganic and medicinal chemistry; vol. 28; 2; (2020);,
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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. 177906-48-8, name is trans-N-Boc-1,4-cyclohexanediamine belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of trans-N-Boc-1,4-cyclohexanediamine

tert-Butyl (lr,4r)-4-(dimethylamino)cyclohex lcarbamate (SB1-E-21-2) To a solution of SB1-E-21-1 (850 mg, 3.97 mmol) and HCHO (600 mg, 20.0 mmol) in MeOH (30 mL) was added NaBH3CN (1.1 g, 17.5 mmol), the mixture was stirred at r.t overnight, after completion, concentrated to remove the solvent, the residue was extracted with ethyl acetate (100 mL chi 4), the organic phase was washed with brine (50 mL chi 2), dried with Na2S04. Filtered, concentrated to remove the solvent, the residue was purified by silica gel (DCM/MeOH = 10/1, 5/1) to obtain SB1-E-21-2 (light brown solid, 800 mg, yield 83%). LCMS (m/z): 243 [M + H]+.

The synthetic route of 177906-48-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DANA-FARBER CANCER INSTITUTE, INC.; GRAY, Nathanael, S.; ZHANG, Tinghu; KWIATKOWSKI, Nicholas, Paul; (299 pag.)WO2016/160617; (2016); A2;,
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Related Products of 782-45-6, 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. 782-45-6, name is 4-Amino-N-phenylbenzamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

The pale yellow solid was dissolved in 20 ml of dry methylene chloride solution, c was added, and a solution of triethylamine (0.07 ml) in dry dichloromethane was added dropwise. The mixture was stirred overnight at room temperature, checked by TLC, filtered, dried and treated with 10 ml of acetic acid Ethyl acetate was heated to reflux, filtered and dried to give 0.138g of a yellow solid in 58% 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, 4-Amino-N-phenylbenzamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Chinese Academy Of Medical Sciences Pharmaceutical Institute; Xiao Zhiyan; Ye Fei; Tang Yanbo; Tian Jinying; Guo Zongru; Chen Zheng; Zhang Xiaolin; He Yibo; Ma Yiming; Chen Ling; Han Jing; (27 pag.)CN102382076; (2016); B;,
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Synthetic Route of 144072-29-7,Some common heterocyclic compound, 144072-29-7, name is tert-Butyl (4-(hydroxymethyl)phenyl)carbamate, molecular formula is C12H17NO3, 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.

b) 4-Aminobenzyl N-(4-(4-amino-7-tetrahydro-2H-4-pyranyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-methoxyphenyl)carbamate. Phenyl N-[4-(4-amino-7-tetrahydro-2H-4-pyranyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-methoxyphenyl]carbamate (51 mg, 0.111 mmol) was mixed with tert-butyl N-(4-(hydroxymethyl)phenyl)carbamate (119 mg, 0.533) in pyridine (0.8 mL). The reaction mixture was heated at 100 C. overnight. The solvent was removed and the residue was purified by preparative reverse phase LC/MS to give 4-aminobenzyl N-(4-(4-amino-7-tetrahydro-2H-4-pyranyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-methoxyphenyl)carbamate (9 mg, 0.015 mmol). 1H NMR (CDCl-d) delta1.52(s, 1H), 2.08(m, 4H), 3.65 (m, 2H), 3.90 (s, 3H), 4.14(m, 2H), 4.97 (m, 1H), 5.17 (s, 2H), 5.37(bs, 1H), 6.55 (s, 1H), 6.95 (s, 1H), 7.03 (s, 1H), 7.06 (m, 1H), 7.31(s, 1H), 7.38 (m, 3H), 8.16 (bs, 1H), 8.30 (s, 1H). LC/MS: MH+589.

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 (4-(hydroxymethyl)phenyl)carbamate, its application will become more common.

Reference:
Patent; Hirst, Gavin C.; Calderwood, David; Munschauer, Rainer; Arnold, Lee D.; Johnston, David N.; Rafferty, Paul; US2003/153752; (2003); A1;,
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25216-74-4, name is tert-Butyl (3-bromophenyl)carbamate, 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. Safety of tert-Butyl (3-bromophenyl)carbamate

A mixture of 4-cyanobenzeneboronic acid (14.7 g, 0.10 mol), 3-bromo-phenyl-carbamic acid tert-butyl ester (27.2 g, 0.10 mol), Pd(Ph3P)4 (11.6 g, 0.01 mol) and K2CO3 (21 g, 0.15 mol) in DMF/H2O (1:1, 350 mL) was stirred under argon at 80 C. overnight. The DMF was evaporated under reduced pressure, and the residue was dissolved in EtOAc (200 mL). The mixture was washed with water and brine, dried over Na2SO4, and concentrated to dryness. The residue was purified by column chromatography (petroleum ether/EtOAc 50:1) on silica gel to give (4′-cyano-biphenyl-3-yl)-carbamic acid tert-butyl ester (17 g, 59%). 1H NMR (300 MHz, DMSO-d6) delta 9.48 (s, 1H), 7.91 (d, J=8.4 Hz, 2H), 7.85 (s, 1H), 7.76 (d, J=8.4 Hz, 2H), 7.32-7.48 (m, 3H), 1.47 (s, 9H).

The synthetic route of 25216-74-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Vertex Pharmaceuticals Incorporated; Van Goor, Fredrick F.; Burton, William Lawrence; US2015/231142; (2015); A1;,
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Related Products of 3073-59-4, A common heterocyclic compound, 3073-59-4, name is N,N’-(Hexane-1,6-diyl)diacetamide, molecular formula is C10H20N2O2, 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.

Example 11 (Synthesis of methyl 1,6-hexamethylenedicarbamate) A glass test tube (outer diameter: 10 mm; length: 100 mm) having a cap was filled with 0.112 g (2.78 mmol) of magnesium oxide, 0.010 g (0.0275 mmol) of zinc(II) trifluoromethanesulfonate, 0.502 g (2.50 mmol) of hexamethylenebis(acetamide), and 0.905 g (10.0 mmol) of dimethyl carbonate, and a reaction was conducted at 180C for 2 hours. After cooling to room temperature, the resultant reaction solution was analyzed by gas chromatography. As a result, it was found that the conversion of 1,6-hexamethylenediacetamide was 99.8%, the yield of methyl 1,6-hexamethylenedicarbamate was 83.9 mol%, and the yield of methyl 1,6-hexamethylenemonocarbamate mono acetamide was 8.1%.

The synthetic route of 3073-59-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Ube Industries, Ltd.; EP2325167; (2011); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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 703-12-8 as follows. Safety of 4-Bromo-N-methylbenzenesulfonamide

To a solution of 4-bromo-N-methylbenzenesulfonamide (2, 1.05 g, 4.20 mmol) and triisopropyl borate (1.45 mL, 6.30 mmol) in tetrahydrofuran (8.40 mL) was added n-Butyl Lithium (4.20 mL, 10.5 mmol) at -70 C. The mixture was slowly warmed to 0 C, then 10% HCl solution was added until pH 3-4. The resulting mixture was extracted with EtOAc. The organic layer was extracted with NaOH (2M) and the aqueous phase washed with diethyl ether. The aqueous phase was acidified to pH 3, extracted with EtOAc (impurities and unconsumed reactant were still present) was dried over Na2SO4, and evaporated under reduced pressure. The residue was triturated with diethyl ether to give [4- (methylsulfamoyl)phenyl]boronic acid (187 mg, 0,8700 mmol, 21% yield). (0781) Analytical data: (0782) 1H NMR (200 MHz, DMSO) delta 7.96 (d, J = 8.1 Hz, 2H), 7.72 (d, J = 8.0 Hz, 2H), 7.42 (q, J = 4.9 Hz, 1H), 2.39 (d, J = 5.0 Hz, 3H); (0783) 13C NMR (50 MHz, DMSO) delta 140.6, 134.8, 125.7, 28.8.

According to the analysis of related databases, 703-12-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; HEPAREGENIX GMBH; PRAEFKE, Bent; KLOeVEKORN, Philip; SELIG, Roland; ALBRECHT, Wolfgang; LAUFER, Stefan; (157 pag.)WO2019/149738; (2019); 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. 147291-66-5, name is tert-Butyl 3-aminobenzylcarbamate, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of tert-Butyl 3-aminobenzylcarbamate

EXAMPLE 5A; A mixture of EXAMPLE 1B (1 0 g), tert-butyl 3-aminobenzylcarbamate (1 373 g), HATU (2.348 g) and TEA (2.347 mL) in DMF (30 mL) was stirred at room temperature for 24 hours, then diluted with water and extracted with ethyl acetate The ethyl acetate phase was washed (brine), dried (MgSO4) and filtered The filtrate was evaporated to dryness to leave an oil which was triturated with water The resulting precipitate was filtered and dried

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 147291-66-5.

Reference:
Patent; ABBOTT LABORATORIES; WO2009/12312; (2009); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics