Tag: M.W=100-200

869494-16-6, 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. 869494-16-6, name is tert-Butyl 3,6-diazabicyclo[3.1.1]heptane-6-carboxylate, A new synthetic method of this compound is introduced below.

A suspension of 3,6-diaza-bicyclo[3.1.1]heptane-6-carboxylic acid tert-butyl ester (182 mg, 0.918 mmol), 2-fluoro-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)pyridine (819 mg, 3.67 mmol) and K2C03(S) (634 mg, 4.59 mmol) in DMSO (918 was heated to 90 ¡ãC, then treated with water (5 mL). The resulting mixture was stirred for 1 hour at 90 ¡ãC, then cooled to ambient temperature and filtered to cleanly provide the title compound (1.0 g, 41percent yield). MS (apci) m/z = 320.1 (M+H).

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Reference:
Patent; ANDREWS, Steven W.; BLAKE, James F.; HAAS, Julia; JIANG, Yutong; KOLAKOWSKI, Gabrielle R.; MORENO, David A.; REN, Li; WALLS, Shane M.; (421 pag.)WO2018/136661; (2018); A1;,
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Some common heterocyclic compound, 64214-66-0, name is 4-Chloro-N-methoxy-N-methylbutanamide, molecular formula is C6H12ClNO2, 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. 64214-66-0

Step B 3-chloropropyl 3,5-dimethylphenyl ketone A solution of 10.2 mL (13.9 g; 72 mmol) 5-bromo-m-xylene in 200 mL of anhydrous tetrahydrofuran was stirred under nitrogen at -78 C. as 35.8 mL (84 mmol) of 2.5M n-butyllithium in tetrahydrofuran was added dropwise. After 15 minutes at -78 C., a solution of 10.0 g (60 mmol) of 4-chloro-N-methoxy-N-methylbutyramide (from Step A) in 30 mL of anhydrous tetrahydrofuran was added dropwise over 25-30 minutes. The resulting solution was maintained at -78 C. for 45 minutes and then warmed briefly to room temperature. The reaction was quenched by addition of 40 ml of 2N hydrochloric acid and then partitioned between ethyl acetate and water. The organic phase was washed with saturated aqueous sodium bicarbonate solution and then saturated aqueous sodium chloride solution. The organic solution was dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography of the residue afforded 8.91 g (70%) of an oil, which had satisfactory purity by 1 H NMR (CDCl3).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 64214-66-0, its application will become more common.

Reference:
Patent; Merck & Co., Inc.; US5756507; (1998); A;,
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815-06-5, 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. 815-06-5, name is N-Methyl-2,2,2-trifluoroacetamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Step A: Preparation of 2,2,2-trifluoro-N-(hex-5-enyl)-N-methylacetamide 31a. Sodium hydride (60% dispersion in mineral oil, 31.5 g, 1.28 eq.) was slowly added under nitrogen atmosphere to a solution of N-methyl-2,2,2-trifluoroacetamide (100 g, 1.28 eq.) in DMF (500 mL) at 0 C. The reaction mixture was stirred for 90 min at 0 C., and then 6-bromo-1-hexene (100 g, 1 eq.) was added dropwise over 45 min. The reaction mixture was allowed to warm up to room temperature, and stirred for 3 days at room temperature. The reaction mixture was then poured into water and extracted tree time with EtOAc. The combined organics layers were dried over anhydrous sodium sulphate and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel to produce compound 31a as colorless oil in 56% yield. 1H NMR (DMSO-d6, 400 MHz) delta 1.27-1.38 (m, 2H), 1.48-1.60 (m, 2H), 2.00-2.06 (m, 2H), 2.93-3.07 (2m, 3H), 3.35-3.40 (m, 2H), 4.92-5.04 (m, 2H), 5.73-5.83 (m, 1H).

The synthetic route of 815-06-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Idenix Pharmaceuticals, Inc.; US2009/202480; (2009); A1;,
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Adding some certain compound to certain chemical reactions, such as: 27366-72-9, name is 2-(Dimethylamino)ethanethioamide hydrochloride, 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 27366-72-9. 27366-72-9

EXAMPLE 1 Preparation of Ethyl 2-Dimethylaminomethyl-4-thiazolecarboxylate A reaction mixture was prepared containing 15.5 g. of dimethylaminothioacetamide hydrochloride, 20.5 g. of ethyl bromopyruvate and 100 ml. of ethanol. The reaction mixture was heated to refluxing temperature for about four hours after which time the solvent was removed in vacuo in a rotary evaporator. The residue, containing ethyl 2-dimethylaminomethyl-4-thiazolecarboxylate hydrochloride formed in the above reaction, was dissolved in a mixture of ether and water. The aqueous layer was separated. The ether layer was extracted with an equal volume of water and then discarded. The two aqueous layers were combined and washed with ether. The ether layer was again discarded and the aqueous layer cooled to a temperature in the range of 0-5 C. Solid potassium carbonate was added until the aqueous layer gave a basic reaction to litmus. An oil separated comprising ethyl 2-dimethylaminomethyl-4-thiazolecarboxylate free base. The oily layer was extracted with ether and the ether extract separated and dried. The ether was removed by evaporation in vacuo. The resulting residue was purified by gradient high pressure liquid chromatography (silica, ethyl acetate). Ethyl 2-dimethylaminomethyl-4-thiazolecarboxylate thus obtained had the following physical characteristics: Analysis Calculated: C, 50.45; H, 6.59; N, 13.07; S, 14.96 Found: C, 50.13; H, 6.39; N, 12.89; S, 15.04. The nmr spectrum in CDCl3 (TMS internal standard) gave the following signals (delta): 1.43 (triplet, 3H), 2.40 (singlet, 6H), 3.87 (singlet, 2H), 4.47 (quartet, 2H), 8.20 (singlet, 1H).

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 2-(Dimethylamino)ethanethioamide hydrochloride.

Reference:
Patent; Eli Lilly and Company; US4474794; (1984); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Some common heterocyclic compound, 354-38-1, name is 2,2,2-Trifluoroacetamide, molecular formula is C2H2F3NO, 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. 354-38-1

(rac)-2,2,2-Trifluoro-N-[methyl(3-nitrobenzyl)oxido-lambda6-sulfanylidene]acetamide To a suspension of (rac)-1-[(methylsulfinyl)methyl]-3-nitrobenzene (16.6 g; 83.1 mmol), trifluoroacetamide (18.8 g; 166.1 mmol), magnesium oxide (13.4 g; 332.3 mmol) and rhodium(II)-acetat dimer (1.7 g; 8.3 mmol) in DCM (2290 mL) was added iodobenzene diacetate (40.1 g; 124.6 mmol) at room temperature. The batch was stirred for 16 hours at room temperature, filtered and concentrated. The residue was purified by chromatography (DCM / ethanol 97:3) to give the desired product (25.6 g; 82.4 mmol). 1H NMR (400MHz, CDCl3, 300K) delta = 8.36 (m, 1H), 8.31 (m, 1H), 7.80 (m, 1H), 7.69 (m, 1H), 4.91 (d, 1H), 4.79 (d, 1H), 3.28 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 354-38-1, its application will become more common.

Reference:
Patent; Bayer Intellectual Property GmbH; EP2527332; (2012); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

609-66-5, 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. 609-66-5 name is 2-Chlorobenzamide, 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.

General procedure: To a 25 mL Schlenk tube containing a solution of 2 in 2 mL of THF was added amide (1.0 mmol) and (EtO)3SiH (0.50 g, 3.0 mmol). The reaction mixture was stirred at 60 C until there was no amide left (monitored by TLC and GC-MS). The product was purified according to literature procedures by Beller

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:
Article; Ren, Shishuai; Wang, Yangyang; Yang, Fei; Sun, Hongjian; Li, Xiaoyan; Catalysis Communications; vol. 120; (2019); p. 72 – 75;,
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Amide – an overview | ScienceDirect Topics

147962-41-2, name is N-Propylsulfamide, 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. 147962-41-2

General procedure: Under nitrogen atmosphere, a mixture of sulfonamide 2a-h (1 mmol), maleic anhydride derivatives (2 mmol), and H6P2W18O62 catalyst (2 mmol%) in acetonitrile (2 mL), was stirred at reflux. Reaction was monitored by TLC. After achieving the reaction, dichloromethane (2 ¡Á10 mL) was added and the catalyst was filtered; water (10 mL) was then added. The organic layers were combined and dried over anhydrous sodium sulfate and removed under reduced pressure. The residue obtained was purified by flash chromatography (Merck silica gel 60H, CH2Cl2/MeOH, 9:1) to afford the corresponding sulfonyl maleimide derivatives.

Statistics shows that 147962-41-2 is playing an increasingly important role. we look forward to future research findings about N-Propylsulfamide.

Reference:
Article; Bougheloum, Chafika; Guezane Lakoud, Samia; Belghiche, Robila; Messalhi, Abdelrani; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 191; 10; (2016); p. 1344 – 1350;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

57561-39-4, 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. 57561-39-4, name is tert-Butyl (2-hydroxyethyl)(methyl)carbamate, A new synthetic method of this compound is introduced below.

To a well-stirred solution of N-Boc-N-Me-glycinol (3.5 g, 20 mmol) in DMSO (20 mL) cooled with an ice-water bath was add allyl bromide (3.6 g, 30.0 mmol), followed by finely ground KOH powder (3.5 g, 30.0 mmol) over 15 minutes. The resulting solution was stirred for overnight at room temperature. The resulting mixture was partitioned between 5% aq. HOAc (50mL) and ethyl acetate (200ml). The organic layer was separated, washed with brine, dried with sodium sulfate, filtered, and concentrated, then purified by flash chromatography eluting with 10% to 80% ethyl acetate/hexane. Yield of product 4.1g, 95%. Ion(s) found by LCMS: M+H =216.3.

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; CIDARA THERAPEUTICS, INC.; BALKOVEC, James, M.; BENSEN, Daniel, C.; BORCHARDT, Allen; BRADY, Thomas, P.; CHEN, Zhi-Yong; COLE, Jason; DO, Quyen-Quyen, Thuy; DOEHRMANN, Simon; JIANG, Wanlong; LAM, Thanh; NONCOVICH, Alain; TARI, Leslie, W.; (797 pag.)WO2020/51498; (2020); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

The chemical industry reduces the impact on the environment during synthesis 711007-44-2, name is 2,3-Diaminobenzamide, I believe this compound will play a more active role in future production and life. 711007-44-2

General procedure: In a dark environment, a mixture of 2,3-diaminobenzamide(1.51 g, 10 mmol), PYTZ (20 mg), and ethanol (200 mL)was taken in an open pear-shaped bottle, stirred magneticallyat room temperature, and then aldehyde (10 mmol) wasadded slowly in 2 min. The bottle was exposed to visiblelight (Xenon, 10 A) under stirring condition. The reactionwas monitored by TLC. After the reaction completed, thereaction mixture was transferred to a three-neck bottle outsideof the photochemical reactor and air was introduced toensure that the intermediate was completely oxidized. Then,the solvent was evaporated in vacuum to 40 mL until thesolid appeared. The mixture was cooled down in an ice bathfor crystallization, filtration. The crude solid was recrystallizedfrom 25 mL ethanol (30 C) to get the target products.

The chemical industry reduces the impact on the environment during synthesis 711007-44-2. I believe this compound will play a more active role in future production and life.

Reference:
Article; Zhang, Li-Jie; Yang, Kang; Li, Chun-Yu; Sun, Ya-Quan; Chemical Papers; vol. 73; 11; (2019); p. 2697 – 2705;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

711007-44-2, Adding some certain compound to certain chemical reactions, such as: 711007-44-2, name is 2,3-Diaminobenzamide, 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 711007-44-2.

To a 100 ml three-neck flask was added 2,3-diaminobenzamide (3.2 g, 20 mmol), compound C (4.47 g, 22 mmol), sulfur powder (3.2 g, 100 mmol) was added, and stirred at 170 C. After 6 h, after cooling, 60 ml of methylene chloride was added to dissolve, and the silica gel was mixed and concentrated on a silica gel column. Chromatography on a silica gel column afforded the target product (C3) 0.76 g (yield: 11%).

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 711007-44-2.

Reference:
Patent; Shandong University Qilu Hospital; Tan Bingxu; (9 pag.)CN107556288; (2018); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics