Amides-buliding-blocks

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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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. 17641-08-6, name is 2-Chloro-N-(3-methoxyphenyl)acetamide, A new synthetic method of this compound is introduced below., HPLC of Formula: C9H10ClNO2

2) 2-chloro-N-(3-methoxyphenyl)acetamide (3.1g, 16 mmol) and anhydrous AlCl3 powder (4.4g,32 mmol) is heated and stirred at 120C for 10 minutes and exhibit a melting state. The temperature is elevated gradually to 240C in 40 minutes and then stirred 5 minutes. The reaction is allowed to cool to obtain a brown powder. The solid powder is poured into a mixture of 100g of crushed ice and 50ml of concentrated hydrochloric acid. The mixture is stirred for 10 minutes and then reflux for 10 minutes, and allowed to cool to precipitate a light yellow powder, which is filtered out and recrystallized in water to obtain 1.5g of 6-hydroxy-indoline-2-one, with a yield of 62%.

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; Jiangsu Guohua Investment Co., Ltd; Shanghai Institute of Pharmaceutical Industry; EP2322520; (2011); A1;,
Amide – Wikipedia,
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Electric Literature of 142-26-7, A common heterocyclic compound, 142-26-7, name is N-Acetylethanolamine, molecular formula is C4H9NO2, 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.

The title product of Preparation 29 (600 mg, 2.16 mmol), N-(2-hydroxyethyl)acetamide (276 mg, 2.68 mmo), triphenylphosphine (710 mg, 2.71 mmol) were mixed under Ar atmosphere followed by the addition of dry THF (5 ml). The mixture was cooled at 0 and DIAD was added drop wise. The reaction mixture was allowed to warm to rt and then stirred overnight. Solvent was removed and the residue thus obtained was partitioned between water and ethyl acetate. The organic layer was washed with water and brine. It was dried and solvent removed to yield a crude product that was purified according to purification method A to yield the title compound as a solid. 130 mg (17% yield) of the title product were obtained as a solid.LRMS: m/z 363 (M+1fRetention time: 4.32 min (method B)H NMR (200 MHz, DMSO-D6) delta ppm 0.92 (t, 3 H) 1.29 – 1.45 (m, 2 H) 1.55 (d,J=7.14 Hz, 2 H) 1.77 (s, 3 H) 2.20 (s, 6 H) 3.06 (t, J=6.59 Hz, 2 H) 3.24 – 3.45(m, 2 H) 3.85 – 4.01 (m, 2 H) 7.23 (s, 2 H) 7.96 – 8.07 (m, 1 H) 8.85 – 8.93 (m, 1H)

The synthetic route of 142-26-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ALMIRALL, S.A.; GRIMA POVEDA, Pedro Manuel; AGUILAR IZQUIERDO, Nuria; MIR CEPEDA, Marta; CARRASCAL RIERA, Marta; TERRICABRAS BELART, Emma; GRACIA FERRER, Jordi; CASALS COLL, Gaspar; WO2011/35900; (2011); A1;,
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Application of 116861-31-5, The chemical industry reduces the impact on the environment during synthesis 116861-31-5, name is tert-Butyl (3-chloropropyl)carbamate, I believe this compound will play a more active role in future production and life.

[0095] Berbamine dihydrochloride (7.0 g, 10.28 mmol) is dissolved in N,N-dimethyl formamide (150 mL). Under nitrogen atmosphere, the solution is cooled to 0 C. After adding NaH (1.65 g, 60%, 41.12 mmol) into the solution, the mixture is stirred for 1 hour, then the solution of compound (8-2) (2.18 g, 11.3 mmol) in N,N-dimethyl formamide (30 mL) is added dropwise therein over 15 minutes. After being stirred for 1 hour at 0 C., the mixture is allowed to be warmed up to room temperature and is stirred for 3 hours, then is heated to 80 C. overnight. After vacuum evaporation, the reaction mixture is diluted with water and extracted with dichlorometbane (3*150 mL). The combined organic phase is washed with water and brine, dried through, anhydrous sodium sulfate and filtered. After vacuum concentration, the residue is purified by a preparative high performance liquid chromatography to give compound (8-3) (3.0 g, 38.1%).

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 (3-chloropropyl)carbamate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; HANGZHOU BENSHENG PHARACEUTICALS CO., LTD.; Xu, Rongzhen; Xie, Fuwen; Lai, Hongxi; Rong, Frank; US2013/178470; (2013); 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

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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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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Electric Literature of 5238-56-2,Some common heterocyclic compound, 5238-56-2, name is N-(2-Hydroxyethyl)methacrylamide, molecular formula is C6H11NO2, 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.

N-(2-hydroxyethyl) methacrylamide (3.30 mL, 25.6 mmol, 1.0 eq), triethylamine (7.15 mL, 51.2 mmol, 2.0 eq) and 50 mL DCM were added into a 250 mL flask. After the reaction system was cooled down by an ice bath, butyric anhydride (5.00 mL, 30.7 mmol, 1.2 eq) was added dropwise under the protection of nitrogen. The system was allowed to react overnight. The reaction mixture was filtered and washed by NH4CI solution, NaHCCb solution, and water. After dried by anhydrous MgSC , the organic layer was concentrated by rotary evaporation and purified on a silica column using DCM/MeOH. The product N- butanoyloxyethyl methacrylamide (3) was obtained as pale yellow oil (4.56 g, 89.6%) and analyzed by 1H-NMR (500 MHz, CDCb) deltaEta ppm 0.95 (t, 3H, CH2CH2-CH3), 1.66 (m, 2H, CH2-CH2), 1.97 (s, 3H, C(CH2)-CH3), 2.32 (t, 2H, CO-CH2), 3.59 (dt, 2H, NH-CH2), 4.23 (t, 2H, O-CH2), 5.35 (s, IH, CCH2), 5.71 (s, IH, CCH2), 6.19 (br s, IH, NH). This example demonstrates the feasibility of attaching pharmaceutically-active small molecules to a monomeric unit of the block copolymer. Additional SCFAs can be attached to the monomeric unit in a similar manner.

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

Reference:
Patent; THE UNIVERSITY OF CHICAGO; HUBBELL, Jeffrey A.; WANG, Ruyi; WILSON, D. Scott; NAGLER, Cathryn R.; PLUNKETT, Catherine; (90 pag.)WO2018/195067; (2018); 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. 78191-00-1, name is N-Methoxy-N-methylacetamide, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 78191-00-1

To a solution of l-bromo-3-isopropylbenzene (10 g, 0.05 niol) in THF was added dropwise with BuLi (47 mL, 0.075 mol) at -60C. After stirred 30 minutes, -methoxy- -methylacetamide (6,22 g, 0.06 mol) was added. The mixture was stirred at -30C for 3 hours. Then the mixture was quenched with H20, the mixture was partitioned between EtOAc and water. The layer was separated and washed with water, brine, dried over Na2S04, and concentrated. The residue was purified by column chromatography to obtained the titled compound. ‘H NMR (CHLOR OFQRM-d) : delta 7.85 (s, 1H), 7.79 (dt, J = 7.6, 1.4 Hz, 1H), 7.33 – 7.53 (m, 2H), 3.00 (dt, J – 13.8, 6.9 Hz, 1H), 1.30 (d, J – 6.7 Hz, 6H) LC-MS : m/z 163(M+H)+

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 78191-00-1.

Reference:
Patent; RIPKA, Amy S.; SAUNDERS, Jeffrey O.; KAMENECKA, Theodore Mark; GRIFFIN, Patrick R.; WO2013/78240; (2013); A1;,
Amide – Wikipedia,
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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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