Month: March 2021

Some common heterocyclic compound, 205318-52-1, name is 3-(Aminomethyl)-1-N-Boc-aniline, molecular formula is C12H18N2O2, 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. SDS of cas: 205318-52-1

A solution of EXAMPLE 7A (170 mg) in acetonitrile (4 mL) at 25 C. was treated with tert-butyl 3-(aminomethyl)phenylcarbamate (107 mg) and N,N-diisopropylethyl amine (450 muL), heated in a microwave reactor for 10 min at 50 C., and 20 min at 190 C., cooled, treated with tert-butyl (1S,4S)-(-)-2,5-diaza-bicyclo(2.2.1)heptane-2-carboxylate (116 mg), heated in a microwave reactor for 30 min at 100 C., cooled, treated with aqueous lithium hydroxide (2M, 1.2 mL), heated in a microwave reactor for 15 min at 100 C., cooled, stirred for 18 hours at 25 C., diluted with water, acidified to pH 3 with aqueous HCl, and filtered.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 205318-52-1, its application will become more common.

Reference:
Patent; Anderson, David; Beutel, Bruce; Bosse, Todd D.; Clark, Richard; Cooper, Curt; Dandliker, Peter; David, Caroline; Gu, Yu-Gui; Hansen, Todd Matthew; Hinman, Mira; Kalvin, Douglas; Larson, Daniel P.; Lynch, Linda; Ma, Zhenkun; Motter, Christopher; Palazzo, Fabio; Rosenberg, Teresa; Rehm, Tamara; Sanders, William; Tufano, Michael; Wagner, Rolf; Weitzberg, Moshe; Yong, Hong; Zhang, Tianyuan; US2003/232818; (2003); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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. 2895-21-8, name is N-Isopropyl-2-chloroacetamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Product Details of 2895-21-8

(2) To a solution of the compound 2 (112 mg) in dichloromethane (2 mL) was added trifluoroacetic acid (2 mL), andthe reaction mixture was stirred for 1 hour at room temperature. The reaction mixture was diluted with methanol,then the solution was treated with packed strong cation exchange resin (PoraPak Rxn Cx, eluent: a solution of 1mol/L NH3 in methanol), and the eluate was concentrated under reduced pressure. The resulting residue, thecompound 3 (82 mg) and sodium carbonate (64 mg) were suspended in acetonitrile (3 mL), and the suspensionwas stirred for 19 hours at 65 C under argon atmosphere. The reaction mixture was cooled to room temperature,diluted with chloroform, and then washed with water, and dried over anhydrous sodium sulfate. The solvent wasevaporated under reduced pressure, and the resulting residue was purified by silica gel column chromatography(eluent: hexane-ethyl acetate; gradient: 80:20-50:50) to give3-[4-(isopropylcarbamoylmethyl)piperazin-1-yl]-5-phenethyl-1,2,4-triazine (101 mg) as a yellow viscous substance. MS (APCI) 369 [M+H]+

The synthetic route of 2895-21-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Mitsubishi Tanabe Pharma Corporation; USHIROGOCHI, Hideki; SASAKI, Wataru; ONDA, Yuichi; SAKAKIBARA, Ryo; AKAHOSHI, Fumihiko; (158 pag.)EP3135668; (2017); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 132414-81-4, 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. 132414-81-4, name is 5-Boc-hexahydropyrrolo[3,4-b]pyrrole belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A mixture of compound 4a (100 mg, 0.47 mmol) and TEA (260 mg,2.56 mmol) in DCM (10 mL) was added compound 9 (97 mg, 0.52 mmol) stirred at r.t. for 3 hrs under N2 atmosphere. The mixture was diluted with water and extracted with EtOAc. The organic combined layers were washed with brine, dried over Na2SO4, filtered, concentrated and purified by Flash column to give compound 6 (150 mg,yield: 88%). MS (ESI): m/z 364.1 [M + H]+

The synthetic route of 5-Boc-hexahydropyrrolo[3,4-b]pyrrole has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wu, Songliang; Sun, Yu; Hu, Yi; Zhang, Hongmei; Hou, Lijuan; Liu, Xing; Li, Yufeng; He, Haiying; Luo, Zhi; Chen, Yuan; Wang, Yuhe; Shi, Weihua; Shen, Liang; Cao, Changqing; Liang, Wei; Xu, Qing; Lv, Qiang; Lan, Jiong; Li, Jian; Chen, Shuhui; Bioorganic and Medicinal Chemistry Letters; vol. 27; 6; (2017); p. 1458 – 1462;,
Amide – Wikipedia,
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. 88829-82-7, name is tert-Butyl (8-aminooctyl)carbamate, A new synthetic method of this compound is introduced below., Application In Synthesis of tert-Butyl (8-aminooctyl)carbamate

2-(2,6-Dioxopiperidin-3-yl)-4-fluoroisoindoline-1,3-dione (481.6 mg, 1.74 mmol, 1 eq) and tert-butyl (8-aminooctyl)carbamate (467.7 mg, 1.91 mmol, 1.1 eq) were dissolved in NMP (8.7 mL, 0.2M). DIPEA (606 uL, 3.48 mmol, 2 eq) was added and the mixture was heated to 90 C. After 15 hours, the mixture was diluted with EtOAc and washed with 10% citric acid (aq), saturated sodium bicarbonate, water and three times with brine. The organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure. Purification by column chromatography (ISCO, 12 g column, 0-5% MeOH/DCM, 25 minute gradient) afforded the desired product as a yellow oil (0.55 g, 1.099 mmol, 63%).

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; DANA-FARBER CANCER INSTITUTE, INC.; BUCKLEY, Dennis; BRADNER, James; REMILLARD, David Ian; (212 pag.)WO2017/223452; (2017); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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. 120157-97-3, name is N-Boc-2-(4-Bromophenyl)ethylamine, This compound has unique chemical properties. The synthetic route is as follows., name: N-Boc-2-(4-Bromophenyl)ethylamine

Dissolved tert-butyl N-[2-(4-bromophenyl)ethyl]carbamate (?124.95 mmol) in THF (500 mL). Added bis(pinacolato)diboron (44.0 g, 174.93 mmol), palladium chloride diphenyl phosphine ferrocene (10.2 g, 10 mol %) and potassium acetate (36.8 g, 374.85 mmol). Heated to 65 C. for 16 hours. Removed solvent and purified using normal phase chromatography (0-100% EtOAc in heptanes) to yield 40.58 g of product; 1H NMR (400 MHz, CHLOROFORM-d) delta ppm 1.35 (s, 12H) 1.44 (s, 9H) 2.82 (t, J=6.74 Hz, 2H) 3.38 (d, J=5.86 Hz, 2H) 4.18-4.71 (m, 1H) 7.21 (d, J=7.42 Hz, 2H) 7.76 (d, J=7.61 Hz, 2H).

According to the analysis of related databases, 120157-97-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Avista Pharma Solutions, Inc.; Speake, Jason D.; (22 pag.)US10239885; (2019); B1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 224309-64-2, 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. 224309-64-2 name is tert-Butyl (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.

Step B: Tert-butyl 4-oxocyclohexylcarbamate. To a solution of tert-buty 4-hydroxycyclohexylcarbamate ( 1 0.0 g, 46.5 mmol) in DCM ( 100 mL) was added Dess-Martin periodinane (39.4 g, 92.9 mmol) portionwise. The resulting solution was stirred at room temperature overnight, quenched with aq. Na2S203 solution and extracted with DCM (3 x 100 mL). The combined organic layers were washed with water (2 x 100 mL) and brine (100 mL), dried over anhydrous aiSC , and concentrated. The residue was purified by column chromatography on silica gel using petroleum ether / EtOAc (V:V, 10: 1 ) to afford desired product as a white solid.

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

Reference:
Patent; AGIOS PHARMACEUTICALS, INC.; LEMIEUX, Rene M.; POPOVICI-MULLER, Janeta; TRAVINS, Jeremy M.; CAI, Zhenwei; CUI, Dawei; ZHOU, Ding; WO2015/10297; (2015); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 78191-00-1, 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. 78191-00-1, name is N-Methoxy-N-methylacetamide, This compound has unique chemical properties. The synthetic route is as follows.

(Reference Example 17) 1-(4-Methylthiophen-3-yl)ethanone In an argon atmosphere at -78C, 4.0 ml (6.4 mmol) of a 1.6 M hexane solution of n-butyllithium was added dropwise to a diethyl ether (23 ml) solution of 1.0 g (5.3 mmol) of 3-bromo-4-methylthiophene (Tokyo Chemical Industry Co., Ltd.). The mixture was stirred at the temperature for 15 minutes. Next, a diethyl ether (1 ml) solution of 0.70 ml (6.9 mmol) of N-methoxy-N-methylacetamide was added dropwise at -78C, and the mixture was stirred at the temperature for 15 minutes and at room temperature for 23 hours. After the completion of the reaction, a saturated aqueous ammonium chloride solution was added to the reaction mixture liquid, and the resultant mixture was extracted with ethyl acetate. The organic phase was washed with water, dried with anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (eluting solvent: hexane:ethyl acetate = 80:20 (V/V)), and the fraction containing the target compound was concentrated under reduced pressure to give the title compound weighing 552 mg (3.94 mmol, yield 75%) as a light yellow oil. Mass spectrum (CI, m/z): 141 [M+1]+. 1H-NMR spectrum (400MHz, CDCl3) delta: 7.99 (1H, d, J = 3.1 Hz), 6.91 (1H, dq, J = 3.1, 1.0 Hz), 2.53 (3H, s), 2.46 (3H, d, J = 1.0 Hz).

The chemical industry reduces the impact on the environment during synthesis N-Methoxy-N-methylacetamide. I believe this compound will play a more active role in future production and life.

Reference:
Patent; UBE Industries, Ltd.; IWASE, Noriaki; NISHIDA, Hiroshi; OKUDO, Makoto; ITO, Masaaki; KONO, Shigeyuki; MATOYAMA, Masaaki; USHIYAMA, Shigeru; OKANARI, Eiji; MATSUNAGA, Hirofumi; NISHIKAWA, Kenji; KIMURA, Tomio; (54 pag.)EP3162801; (2017); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 14719-21-2, name is 2,2,2-Trifluoro-N-(prop-2-yn-1-yl)acetamide, 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 14719-21-2, category: amides-buliding-blocks

To a mixture of 45 (1.96 g, 5.20 mmol), Cul (103 mg, 0.54 mmol) and tetrakis[triphenylphosphine]palladium[0] (317 mg, 0.276 mmol) in 10 ml of anhydrous DMF was added anhydrous triethylamine (1.1 ml) followed by propargyl trifluoroacetimide (1.50 g, 9.88 mmol). The reaction mixture was stirred under argon for 4 h. The solvent DMF was removed by evaporation and the residual oil was purified by silica gel chromatography eluting with 7% methanol in ethyl acetate. The product fractions were pooled and evaporated affording a foam: 2.16 g (99%) 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, 2,2,2-Trifluoro-N-(prop-2-yn-1-yl)acetamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Epoch Biosciences, Inc.; US6699975; (2004); B2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 53844-02-3, 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. 53844-02-3, name is Benzyl (2-bromoethyl)carbamate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To a solution of 1 (15.0mmol) in CH3CN (60mL) were added K2CO3 (3.10g, 22.5mmol) and N-Cbz-2-bromoethylamine (3.87g, 15.0mmol) under stirring. It was then kept at 80C, and monitored by TLC (Hexane/EtOAc=2/1, v/v). Next, K2CO3 was removed by filtration. The filtrate was concentrated to give a light brown oil. The oil was dissolved in ethyl acetate (150mL) and the solution was washed with water (2¡Á50mL). The organic phase was dried over anhydrous Na2SO4 and concentrated under reduced pressure to afford the crude product. The residue was concentrated and purified by silica gel column chromatography (Hexane/EtOAc=4/1, v/v) to give a white solid

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, Benzyl (2-bromoethyl)carbamate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Ao, Chunyan; Men, Jian; Wang, Yang; Shao, Tao; Huang, Yuanyuan; Huo, Junji; Gao, Guowei; Tetrahedron Asymmetry; vol. 27; 13; (2016); p. 589 – 595;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 104060-23-3,Some common heterocyclic compound, 104060-23-3, name is N-Boc-2-(4-Aminophenyl)ethanol, molecular formula is C13H19NO3, 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.

4-(tert-Butoxycarbonylamino)phenethyl 3-nitro-benzenesulfonate 4.25 g (42 mmole) triethylamine was added to 10 g (42 mmole) 2-[4-(tert-butoxycarbonylamino)phenyl]-1-ethanol dissolved in dichloromethane. The reaction mixture was cooled to -25 C. and 9.34 g (42 mmole) 3-nitrobenzenesulfonyl chloride was added in portions. The reaction mixture was poured on to icewater, the phases were separated and the organic phase was dried (sodium sulfate), filtered and the solvent was evaporated in vacuo. The residue was purified by chromatography on silica gel using dichloromethane as eluent to give 8.3 g (yield 47%) 4-(tert-butoxycarbonylamino)-phenethyl 3-nitro-benzenesulfonate as yellow crystals.

The synthetic route of 104060-23-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AstraZeneca AB; US6288096; (2001); B1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics