Tag: M.W=200-300

Application of 142733-64-0, These common heterocyclic compound, 142733-64-0, name is tert-Butyl (cis-3-(hydroxymethyl)cyclobutyl)carbamate, 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.

Under nitrogen protection,Compound 3-Boc aminocyclobutylmethanol (83f) (350.0 mg, 1.7 mmol)And triethylamine (528.0 mg, 5.2 mmol) was dissolved in 10 mL of dichloromethane.Under ice water bath, methylsulfonyl chloride (219.0 mg, 1.9 mmol) was added dropwise.Stir at room temperature for 3 h.Dichloromethane and 0.2 N of dilute hydrochloric acid were added and extracted.The organic layer was washed twice with brine, dried and dried.The compound 3-((tert-butoxycarbonyl)amino)cyclobutyl)methyl methanesulfonate (83 g) (330.0 mg, 1.2 mmol)The next reaction was directly administered, and the yield was 67.9%.

The synthetic route of 142733-64-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chengdu Haichuang Pharmaceutical Co., Ltd.; Du Wu; Wen Kun; Ai Chaowu; He Jinyun; Li Xinghai; Chen Yuanwei; (28 pag.)CN109988120; (2019); A;,
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 177906-48-8 as follows. Application In Synthesis of trans-N-Boc-1,4-cyclohexanediamine

To a solution of 6-bromo-2-fluoro-8-(trifluoromethyl)quinazoline (0.4 g, 1.3 mmol) in n-BuOH (20.0 mL) were added tert-butyl N-(4-aminocyclohexyl)carbamate (349 mg, 1.6 mmol) and DIEA (350 mg, 2.7 mmol, 472.3 uL). The mixture was stirred at 100C for 12 h. The mixture was cooled to 25C and filtered. The cake was washed with Petroleum ether (50.0 mL) to afford tert-butyl ((lr,4r)-4-((6-bromo-8-(trifluoromethyl)quinazolin-2- yl)amino)cyclohexyl) carbamate (0.5 g, 1.0 mmol, 74.6% yield). M+H+ = 491.2 (LCMS).

According to the analysis of related databases, 177906-48-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; QUENTIS THERAPEUTICS, INC.; VACCA, Joseph P.; LI, Dansu; BETTIGOLE, Sarah; (184 pag.)WO2018/222918; (2018); 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. 29579-11-1, name is 2-(Benzyloxy)benzamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 29579-11-1

General procedure: The appropriate amide 32a-p, benzhydrazide (40a), or p-toluenesulfonylhydrazide (43a) (1.0 mmol, 1.0 equiv) was placed in a SchlenkKjeldahl reaction flask and the flask was evacuated/argon re-filledthree times. Subsequently, anhyd CH2Cl2 (25 mL) was added and themixture was stirred at r.t. for 10 min before dropwise addition of oxalylchloride (3.0 mmol, 3.0 equiv) followed. The reaction mixturewas then stirred at reflux for 2.5-3.0 h before cooling to r.t. and thesolvent was evaporated in vacuo. Subsequently, the appropriate nucleophile32, 34, 36, 38, 40, 42, 43, or 45 (1.1-1.25 mmol, 1.1-1.25equiv) was rapidly added and the flask was evacuated/argon re-filledbefore anhyd toluene (12 mL) was added. The reaction mixture wasthen stirred at reflux for 2.5-3 h before cooling to r.t. and concentrationto about 1/3 of the initial volume on rotavapor. Hexane was addedto the residue and the obtained precipitate (often sonicated) wascollected by filtration under reduced pressure to yield the crudeproduct. When necessary, the isolated material was purified either bycrystallization from MeOH or flash chromatography on silica gel withhexane-EtOAc as the eluent.

The synthetic route of 29579-11-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Hernandez, Anolan Garcia; Grooms, Gregory M.; El-Alfy, Abir T.; Stec, Jozef; Synthesis; vol. 49; 10; (2017); p. 2163 – 2176;,
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. 85006-25-3, name is tert-Butyl (tert-butoxycarbonyl)oxycarbamate, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 85006-25-3

General procedure: Method D: To a solution of acyl Meldrum?s acid (1.69mmol, 1.8equiv) in dry toluene (4.5mL) at room temperature was added N,O-bis(tert-butoxycarbonyl)hydroxylamine (219mg, 0.938mmol, 1.0equiv), and the reaction mixture was immersed in an oil bath preheated to 90C. The reaction was monitored for the complete consumption of N,O-bis(tert-butoxycarbonyl)hydroxylamine. Leaving the reaction for longer time can lead to loss in yield and competing side reactions. After concentration in vacuo, the residue was purified on silica gel chromatography using 5% ethyl acetate in hexane to yield beta-keto hydroxamic acid (12a, d, f-i, l, p) as colorless oil.

According to the analysis of related databases, 85006-25-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Verma, Astha; Wong, Dawn M.; Islam, Rafique; Tong, Fan; Ghavami, Maryam; Mutunga, James M.; Slebodnick, Carla; Li, Jianyong; Viayna, Elisabet; Lam, Polo C.-H.; Totrov, Maxim M.; Bloomquist, Jeffrey R.; Carlier, Paul R.; Bioorganic and Medicinal Chemistry; vol. 23; 6; (2015); p. 1321 – 1340;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 18469-37-9, name is 4-Bromo-N,N-dimethylbenzamide, 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 18469-37-9, SDS of cas: 18469-37-9

N,N-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (0243) To a solution of 4-bromo-N,N-dimethylbenzamide (11.0 g, 48.23 mmol) in dioxane (300 mL) were added 4,4,5,5-tetramethyl-2-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,2-dioxaborolane (14.7 g, 57.89 mmol), Pd(dppf)Cl2 (3.5 g, 4.78 mmol) and potassium acetate (14.2 g, 144.69 mmol) at room temperature. The resulting mixture was stirred for 16 h at 100 C. The reaction mixture was cooled to room temperature and the resulting solid was removed by filtration. The filtrate was concentrated under reduced pressure and the resulting residue was purified by flash chromatography eluting with EtOAc in hexane (0% to 40% gradient) to yield N,N-dimethyl-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide as orange solid (10.0 g, 70%). MS: m/z=276.0 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Bromo-N,N-dimethylbenzamide, and friends who are interested can also refer to it.

Reference:
Patent; Merck Patent GmbH; SHERER, Brian A.; KARRA, Srinivasa; XIAO, Yufang; (407 pag.)US2016/376283; (2016); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 6312-87-4, These common heterocyclic compound, 6312-87-4, name is N-(4-Phenoxyphenyl)acetamide, 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.

General procedure: Dimethylformamide (3 mmol) was added to N-phenylacetamides(2a-2g, 1 mmol) in an ice bath, then phosphoryl chloride(15 mmol) was added dropwise to the mixture and was stirredat ice bath for 20 min, then the reaction proceeded at temperature80e90 C for 7e10 h. After completion of the reaction, ice is addedto the mixture and was stirred, then the formed precipitate wasfiltrated and recrystallized in ethanol [31]. Compounds 3a, 3c, 3d, 3f and 6a were reported in the literatures[32e35].2.3.1. 2-Chloro-6-phenoxyquinoline-3-carbaldehyde (3b)Yellow solid; yield: 61%; mp: 110e113 C; 1H NMR (300 MHz-CDCl3) d 7.18e7.20 (d, 2H, J 6 Hz, AreH), 7.26e7.30 (t, 1H, J 6 Hz,AreH), 7.47e7.53 (m, 2H, AreH), 7.75e7.79 (m, 2H, AreH),8.08e8.11 (d, 1H, J 9 Hz, AreH), 8.92 (s, 1H, AreH), 10.37 (s, 1H,CHO).

The synthetic route of 6312-87-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Mirzaei, Salimeh; Hadizadeh, Farzin; Eisvand, Farhad; Mosaffa, Fatemeh; Ghodsi, Razieh; Journal of Molecular Structure; vol. 1202; (2020);,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 1000698-88-3, name is tert-Butyl (2-amino-4,5-difluorophenyl)carbamate, 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 1000698-88-3, Quality Control of tert-Butyl (2-amino-4,5-difluorophenyl)carbamate

e) N-Benzyl-2-[2-(4-chloro-phenyl)-5,6-difluoro-benzoimidazol-l-yll-2-cyclopentyl- acetamide; To a solution of 5.0 g (20.47 mmol) (2-amino-4,5-difluoro-phenyl)-carbamic acid tert- butyl ester (Example 73, intermediate g) in 50 ml methanol, 2.21 g (22.57 mmol) cyclopentanecarbaldehyde (commercially available) were added. After stirring for 5 min. at room temperature, 3.2 g (20.5 mmol) p-chlorobenzoic acid and 2.5 ml (20.47 mmol) benzyl isocyanide (commercially available) were added. After stirring for 19 h, 38.38 ml (153.52 mmol) 4 M hydrochloric acid in dioxane were added dropwise over 5 min. After 5 h the solution was poured on 500 ml saturated aqueous sodium bicarbonate solution and the phases were separated. The organic layer was extracted three times with ethyl acetate and the combined organic layers were washed with water and brine, dried over magnesium sulfate, filtered, and evaporated. The residue was purified by silica gel chromatography using a MPLC system (CombiFlash Companion, Isco Inc.) eluting with a gradient of n- heptane : ethyl acetate (100 : 0 to 50 : 50). Light yellow foam (97%). MS (Turbo Spray): m/z = 480.1 [M+H].

At the same time, in my other blogs, there are other synthetic methods of this type of compound, tert-Butyl (2-amino-4,5-difluorophenyl)carbamate, and friends who are interested can also refer to it.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; BENSON, Gregory Martin; BLEICHER, Konrad; FENG, Song; GRETHER, Uwe; KUHN, Bernd; MARTIN, Rainer E.; PLANCHER, Jean-Marc; RICHTER, Hans; TAYLOR, Sven; WO2010/28981; (2010); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 16313-66-9, name is 2-Amino-5-bromobenzamide, 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 16313-66-9, category: amides-buliding-blocks

General procedure: A dry 50 mL flask was charged with 2-aminobenzamide 1 (1.1 mmol), 5,5-dimethyl-1,3-cyclohexanedione 2 (1.0 mmol), iodine (0.026 g, 0.01 mmol) and toluene (10.0 mL). The mixture was stirred at 80 C until the reactant 1 was consumed. Then, another equivalent of 2-aminobenzamide was added to the mixture, and refluxed for a few hours. After the completion of the reaction monitored by TLC, toluene was recovered by distillation under reduced pressure, and the residue was purified by silica column chromatography using ethyl acetate and petroleum ether (1:2) as the eluent to give products 6.

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:
Article; Lu, Lian; Zhang, Mei-Mei; Jiang, Hong; Wang, Xiang-Shan; Tetrahedron Letters; vol. 54; 8; (2013); p. 757 – 760;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Some common heterocyclic compound, 71026-66-9, name is tert-Butyl (4-aminophenyl)carbamate, molecular formula is C11H16N2O2, 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. Computed Properties of C11H16N2O2

2,4-dichloro-5-nitro-pyrimidine (95 mg, 0.49 mmol) was placed into a 10 mL round bottom flask, 3 mL of 1,4-dioxane was added, and stirred at room temperature. Tert-butyl (4-aminophenyl) carbamate (100 mg, 0.48 mmol) and N,N-diisopropylethylamine (69 mg, 0.53 mmol) were dissolved in 2 mL of 1,4-dioxane. The resulting solution was added dropwise into the reaction solution as said above. Upon completion of addition, the resulting mixture was stirred at room temperature for 0.5 h, and TLC showed that the raw material was completely conversed. The solvent was removed by rotary evaporation, and the crude product was separated through silica gel column chromatography (petroleum ether/ethyl acetate=10:1, V/V) to obtain tert-butyl (4-(2-chloro-5-nitropyrimidyl-4-amino)-phenyl)carbamate as orange solids (144 mg, yield 82%). 1H NMR (400 MHz, DMSO-d6): delta 10.38 (s, 1H), 9.46 (s, 1H), 9.12 (s, 1H), 7.49 (d, J=8.6 Hz, 2H), 7.39 (d, J=8.6 Hz, 2H), 1.49 (s, 9H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 71026-66-9, its application will become more common.

Reference:
Patent; Li, Honglin; Xu, Yufang; Zhao, Zhenjiang; Liu, Xiaofeng; Zhou, Wei; Bai, Fang; Xue, Mengzhu; Zhang, Lei; Zhang, Youli; US2015/126508; (2015); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 85006-25-3, 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. 85006-25-3, name is tert-Butyl (tert-butoxycarbonyl)oxycarbamate, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: Method D: To a solution of acyl Meldrum?s acid (1.69mmol, 1.8equiv) in dry toluene (4.5mL) at room temperature was added N,O-bis(tert-butoxycarbonyl)hydroxylamine (219mg, 0.938mmol, 1.0equiv), and the reaction mixture was immersed in an oil bath preheated to 90C. The reaction was monitored for the complete consumption of N,O-bis(tert-butoxycarbonyl)hydroxylamine. Leaving the reaction for longer time can lead to loss in yield and competing side reactions. After concentration in vacuo, the residue was purified on silica gel chromatography using 5% ethyl acetate in hexane to yield beta-keto hydroxamic acid (12a, d, f-i, l, p) as colorless oil.

The chemical industry reduces the impact on the environment during synthesis tert-Butyl (tert-butoxycarbonyl)oxycarbamate. I believe this compound will play a more active role in future production and life.

Reference:
Article; Verma, Astha; Wong, Dawn M.; Islam, Rafique; Tong, Fan; Ghavami, Maryam; Mutunga, James M.; Slebodnick, Carla; Li, Jianyong; Viayna, Elisabet; Lam, Polo C.-H.; Totrov, Maxim M.; Bloomquist, Jeffrey R.; Carlier, Paul R.; Bioorganic and Medicinal Chemistry; vol. 23; 6; (2015); p. 1321 – 1340;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics