Tag: M.W=100-200

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. 20348-09-8 name is 2H-Pyrido[3,2-b][1,4]oxazin-3(4H)-one, 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. 20348-09-8

Step 1. 7-Bromo-2H-pyrido[3,2-b]1,4-oxazin-3(4H)-one To a solution of 5.6 g 2H-pyrido[3,2-b]-1,4-oxazin-3(4H)-one dissolved in 85 ml of DMF under nitrogen is added 7.96 g NBS in 50 ml of DMF. This is allowed to stir at room temperature overnight. To this is added 35 ml of water and the mixture is chilled The solid material which separates is filtered and washed with 3*100 ml H2 O. This is then dried under vacuum at 70 C. and then used directly in the next step.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2H-Pyrido[3,2-b][1,4]oxazin-3(4H)-one, and friends who are interested can also refer to it.

Reference:
Patent; Rorer Pharmaceutical Corporation; US4906629; (1990); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

14433-76-2, 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. 14433-76-2, name is N,N-Dimethylcapramide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

the reaction formula of this embodiment is as follows:In a 25 ml reaction flask, add compound 1a (0.3mmol, 0.1561g), compound 2j (3mmol, 0.5980g), water 1.5 muL), toluene (1.5mL) to dissolve the above materials, and stir the reaction at 80 C. The reaction time is 3h After the reaction was completed, the solvent was removed by spin-drying, and the residue was subjected to flash column chromatography (PE: EA = 30: 1) to obtain pure 3aj (0.0850 g) with a yield of 85%.

The synthetic route of N,N-Dimethylcapramide has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Xuzhou Medical University; Wu Nan; Xu Zhou; Mi Jiajia; Li Chuang; Yuan Changyong; Zheng Yan; (15 pag.)CN110668937; (2020); A;,
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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 402-46-0 as follows. 402-46-0

A round bottom flask was charged with 4-fluorobenzenesulfonamide (945 mg, 5.4 mmol), L-proline-t-butyl ester HCl (1.24 g, 6 mmol), and cesium carbonate (4.2 g, 12 mmol) and suspended in 10 ml anhydrous DMSO. The mixture was placed in a preheated oil bath and equipped with a condenser, and heated under nitrogen at 168 oC overnight. HPLC analysis of the mixture indicated complete conversion of the benzenesulfonamide starting material. The mixture was transferred to an Erlenmeyer flask, the reaction pot was diluted with 2 ml of concentrated HCl, and added to the mixture in the Erlenmeyer flask and allowed to stir. The aqueous was then extracted with ethyl acetate (3 x 50 ml), and the combined extracts were washed with water (3 x 15 ml). The volatiles were then removed under vacuum, and 1.24 g of crude material was obtained. The desired intermediate was isolated using MPLC, utilizing a 0 to 60% gradient of acetone in DCM, affording 0.56 g (41%):1H NMR (300 MHz, DMSO-d6)d ppm 7.58 (d, J= 9.0 Hz, 2H), 6.98 (s, 2H), 6.54 (d, J= 9.0 Hz, 2H), 4.28 (d, J= 8.4 Hz, 1H), 2.35-2.22 (m, 2H), 2.04-1.96 (m, 2H).

According to the analysis of related databases, 402-46-0, the application of this compound in the production field has become more and more popular.

Reference:
Article; Ahmed, Gulzar; Elger, Walter; Meece, Frederick; Nair, Hareesh B.; Schneider, Birgitt; Wyrwa, Ralf; Nickisch, Klaus; Bioorganic and Medicinal Chemistry; vol. 25; 20; (2017); p. 5569 – 5575;,
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92136-39-5, 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. 92136-39-5, name is N-Boc-Propargylamine, A new synthetic method of this compound is introduced below.

EXAMPLE 314A tert-butyl allylcarbamate A solution of copper cyanide (1.15 g, 12.9 mmol) in THF (30 mL) at -78 C. was treated slowly with n-butyllithium (16.9 mL, 27.1 mmol), stirred for 15 minutes at -78 C., treated with tributyltin hydride (7.88 g, 7.30 mL, 27.1 mmol) over a period of 5 minutes, stirred for 15 minutes, treated with tert-butyl 2-propynylcarbamate (2.00 g, 12.9 mmol) in tetrahydrofuran (7 mL), stirred at -78 C. for 1 hour, and treated with a 9:1 aqueous solution of ammonium chloride:ammonium hydroxide (250 mL) and dichloromethane (200 mL). The suspension was filtered through a short pad of diatomaceous earth (Celite). The organic phase of the filtrate was washed with brine and concentrated. The residue was purified on silica gel using 1-2% ethyl acetate/heptane to provide the desired product (3.66 g, 63%). 1H NMR (400 MHz, CDCl3) delta 6.08 (dt, B part of an AB system, J=19.3 Hz, 1.3 Hz, 1H); 5.93 (dt, A part of an AB system, J=19.3 Hz, 4.8 Hz, 1H), 4.59 (br s, 1H), 3.78 (br s, 2H), 1.45 (s, 9H), 1.32-1.26, (m, 12H), 0.90-0.85 (m, 15H).

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; Betschmann, Patrick; Burchat, Andrew F.; Calderwood, David J.; Curtin, Michael L.; Davidsen, Steven K.; Davis, Heather M.; Frey, Robin R.; Heyman, Howard R.; Hirst, Gavin C.; Hrnciar, Peter; Michaelides, Michael R.; Muckey, Melanie A.; Rafferty, Paul; Wada, Carol K.; US2005/26944; (2005); 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 6973-09-7 as follows. 6973-09-7

To a solution of Intermediate Example 4 (200 mg, 0.695 mmol) and 5-amino-2- methylbenzenesulfonamide (129.4 mg, 0.695 mmol) in isopropanol (6 ml) was added 4 drops of cone. HCI. The mixture was heated to reflux overnight. The mixture was cooled to rt and diluted with ether (6 ml). Precipitate was collected via filtration and washed with ether. The hydrochloride salt of 5-({4-[(2,3-dimethyl-2H-indazol~6- yl)(methyl)amino]-pyrimidin-2-yl}amino)-2-methylbenzenesulfonamide was isolated as an off-white solid. 1H NMR (400 MHz, d6DMSO+NaHCO3) delta 9.50 (br s, 1 H), 8.55 (br s, 1 H), 7.81 (d, J= 6.2 Hz, 1 H), 7.75 (d, J = 8.7 Hz1 1 H), 7.69 (m, 1 H), 7.43 (s, 1 H), 7.23 (S1 2H), 7.15 (d, J= 8.4 Hz1 1H), 6.86 (m, 1 H), 5.74 (d, J= 6.1 Hz, 1 H), 4.04 (s, 3H), 3.48 (S1 3H)1 2.61 (s, 3H)1 2.48 (s, 3H). MS (ES+, m/z) 438 (M+H).

According to the analysis of related databases, 6973-09-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2007/64753; (2007); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

A common compound: 3984-14-3, name is N,N-Dimethylsulfamide, belongs to amides-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 3984-14-3

lH-pyrazole-4-carboxylic acid, 5-[13-cyclohexyl-10- [[[(dimethylamino)sulfonyl] amino] carbonyl]-3-methoxy-7H-indolo[2,l- a][2]benzazepin-6-yl]-l,3-dimethyl-, methyl ester.; To a solution of 7H-indolo[2,l-alpha][2]benzazepine-10-carboxylic acid, 13- cyclohexyl-S-methoxy–^-^ethoxycarbony^-l^-dimethyl-lH-pyrazol-S-yl]- (120 mg, 0.222 mmol) in TetaF (5 mL), CDI (54.1 mg, 0.334 mmol) was added. The reaction mixture was heated at 6O0C for one hour, and then allowed to cool to room temperature. N,N-dimethylsulfamide (83 mg, 0.667 mmol) and DBU (0.067 mL,0.445 mmol) were then added and the resultant mixture was heated at 6O0C overnight. The reaction was then quenched with IN HCl solution and the product extracted with ethyl acetate (2 x 3OmL). The organic layers were combined, washed with IN HCl solution, brine, dried (MgSC^) and then filtered. Evaporation of solvents gave the curde product as an orange colored thick oil. This material was then purified by preparative etaPLC using Ceta3CN-eta2O-TFA as a solvent system.Homogeneous fractions were combined and concentrated under vacuum to provide the title compound as an orange colored solid, (31.4 mg, 0.049 mmol, 21.87 % yield). MS m/z 646(MH+), Retention time: 2.245min. (basic). IH NMR (500 MHz, CHLOROFORM-D) delta ppm 1.18 – 1.60 (m, 4 H) 1.70 – 2.14 (m, 6 H) 2.49 (s, 3 H) 2.80 – 2.91 (m, 1 H) 3.05 (s, 6 H) 3.24 (s, 3 H) 3.68 (s, br, 3 H) 3.91 (s, 3 H) 4.64 -4.74 (m, br, 1 H) 4.86 – 5.00 (m, br, 1 H) 6.74 (s, 1 H) 6.94 (d, J=2.75 Hz, 1 H) 7.08 (dd, J=8.85, 2.75 Hz, 1 H) 7.35 (dd, J=8.55, 1.53 Hz, 1 H) 7.53 (d, J=8.55 Hz, 1 H)7.75 (d, J=1.22 Hz, 1 H) 7.89 (d, J=8.54 Hz, 1 H) 8.44 (s, 1 H).

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, 3984-14-3, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2009/29384; (2009); A2;,
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. 17193-28-1, name is 1-Amino-1-cyclopentanecarboxamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 17193-28-1

General procedure: To a solution of protected proline (10 mmol) and triethylamine (1.40 ml; 10 mmol) in dry DCM (30 ml), ethyl chloroformate was added dropwise (0.95 ml; 10 mmol) in dry DCM (10 ml). After 30 min, aminoamide (10 mmol) in dry DCM (10 ml) was added to the mixture and the solution was stirred for 5 h. The organic layer was washed with water and aqueous sodium bicarbonate, dried over sodium sulfate and concentrated in vacuo. The residue was crystallised from the appropriate solvents.

The synthetic route of 17193-28-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Panov, Illia; Drabina, Pavel; Hanusek, Jiri; Sedlak, Milos; Tetrahedron Asymmetry; vol. 22; 2; (2011); p. 215 – 221;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

1882-71-9, Adding some certain compound to certain chemical reactions, such as: 1882-71-9, name is 2-Amino-5-methoxybenzamide, 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 1882-71-9.

General procedure: In a sealed tube equipped with a magnetic bar was charged with 2-amino benzamide derivatives (1, 3.67 mmol), cyclic 1,3-diones (2, 3.67 mmol) and TsOH.H2O (1.83mmol) in m-Xylene (5 mL). The reaction mixture was stirred at 150 ¡ãC for 8 h. After completion of the reaction, the reaction mass was cooled to room temperature, diluted with EtOAc, gave a water wash and the organic layer was dried over anhydrous Na2SO4 and concentrated in vacuo. The crude product was purified by flash column chromatography (eluent: ethyl acetate/ n-hexane = 10?90) on silica gel to afford the desired product (4a-k).

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 1882-71-9.

Reference:
Article; Bingi, Chiranjeevi; Kola, Kaushik Yadav; Kale, Ashok; Nanubolu, Jagadeesh Babu; Atmakur, Krishnaiah; Tetrahedron Letters; vol. 58; 11; (2017); p. 1071 – 1074;,
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Amide – an overview | ScienceDirect Topics

326-67-0, A common heterocyclic compound, 326-67-0, name is N-(2-Fluoro-4-methylphenyl)acetamide, molecular formula is C9H10FNO, 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.

Chlorosulfonic acid(20.56 g,176.46 mmol,5 equiv.)was slowly added to N-(2-fluoro-4-methylphenyl)acetamide(5.90 g,35.29 mmol,1 equiv.)keeping the temperature of the reaction mixture below 50 C. The resulting mixture was then heated to 70 C for 4 hours. After cooling to room temperature,the reaction mixture was then poured carefully into ice,the precipitate was filtered,washed well with distilled water and dried to get 7.3 g of crude product as light brown solid. The crude product thus obtained was further used as such without any purification. NMR(CDCI3): delta 9.09(d,J = 7.6 Hz,1H),7.48(bs,1H),7.14(d, J = 10.8 Hz,1H),2.72(s,3H),2.25(s,3H).

The synthetic route of N-(2-Fluoro-4-methylphenyl)acetamide has been constantly updated, and we look forward to future research findings.

Reference:
Patent; INSECTICIDES (INDIA) LIMITED; OAT AGRIO CO., LTD.; IMAI, Tetsuya; KUMAWAT, Surendra Kumar; SINGH, Manish Kumar; CHAUHAN, Pramod Kumar; BHATT, Ashish; SURAMWAR, Nikhil Vilas; SHELKE, Amol Vasant; SINGH, Rajesh Kumar; KISHORE, Ram; (138 pag.)WO2018/51252; (2018); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Some common heterocyclic compound, 402-46-0, name is 4-Fluorobenzenesulfonamide, molecular formula is C6H6FNO2S, 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. 402-46-0

Example 10 27. N-(4-fluorobenzene)sulfonyl-alpha-dehydrovaline.; 3-methyl-2-oxobutyic acid, sodium salt (5.0 g, 36.2 mmol) was slurried in MTBE (25 mL) and cooled to 0 C, then HCI (12.1 N, 3.1 mL) was added. The resulting biphasic was warmed to rt, then saturated with Na2S04. The inorganic solids were filtered and washed with MTBE (25 mL). The combined organics were stripped to give a light-yellow oil. This oil was dissolved in toluene (35 mL) and diethyleneglycol diethyl ether (5 mL) and p-toluenesulfonamide (5.1 g, 29.0 mmol) then methanesulfonic acid (0.19 mL, 2.9 mmol) were added. The resulting mixture was heated at reflux with Dean-Stark removal of water for 24h, then cooled to 5 C. The resulting solid was filtered, and dried to give 5.4 g of crude material, which was recrystallized from MeOH/ water (16 mL/ 38 mL) to give 4.90 g of pure white solid (62% isolated yield). mp 172-173 C. IH-NMR (400 MHz, CD30D) d 7.83-7.86 (m, 2H), 7.22-7.27 (m, 2H), 2.12 (s, 3H), 1.87 (s, 3H); ?3C NMR (100 MHz, CD30D) 166.6,166.3, 163.7, 151.6, 136.7 (2 peaks), 129.9,129.8, 120.8, 115.5, 115.3, 22.0, 20.4 ppm. HRMS calcd for C11H11FNO4S (M-H) : 272.0393, Found: 272.0398.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 402-46-0, its application will become more common.

Reference:
Patent; MERCK & CO., INC.; WO2005/118529; (2005); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics