Tag: M.W=200-300

127828-22-2,Some common heterocyclic compound, 127828-22-2, name is tert-Butyl (2-(2-aminoethoxy)ethyl)carbamate, molecular formula is C9H20N2O3, 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.

tert-Butyl 2-(2-aminoethoxy)ethylcarbamate (570 mg, 2.8 mmol) was taken up in CH3CN (8 mL) and DMF (8 mL) along with Acipimox (435 mg, 2.8 mmol) HATU (1.17 g, 3.1 mmol) and DIEA (730 muL, 4.2 mmol). The resulting reaction mixture was stirred at room temperature for 18 h. It was then diluted with EtOAc (50 mL), washed with water (3*10 mL), brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (9:1 CH2Cl2/MeOH) to afford 5-((2-(2-((tert-butoxycarbonyl)amino)ethoxy) ethyl)carbamoyl)-2-methylpyrazine 1-oxide (810 mg, 85%).

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 (2-(2-aminoethoxy)ethyl)carbamate, its application will become more common.

Reference:
Patent; Milne, Jill C.; Jirousek, Michael R.; Bemis, Jean E.; Vu, Chi B.; US2011/82156; (2011); A1;,
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Adding a certain compound to certain chemical reactions, such as: 283173-80-8, name is 2-Bromo-8-fluoro-4,5-dihydro-1H-azepino[5,4,3-cd]indol-6(3H)-one, 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 283173-80-8, 283173-80-8

l, r-Bis(diphenylphosphino)ferrocene palladium (II) dichloride (2.5 moles, 1.83 kg) was added to a solution of Formula-Al (1.0 moles) in a 1:2 mixture of 4.2 L of dichloromethane and degassed dimethylacetamide. The reaction mass was stirred for 1 hour at about 20 C. Thereafter, the reaction mixture temperature was raised to 95 C and stirred for 1 hour. In a separate vessel, Formula-C3 (1.2 moles) was dissolved in dimethylacetamide (1.1 L) and added to 2.8 L of an aqueous solution of sodium carbonate (2.0 moles) and stirred for 3 hours at 20 C. The contents of the separate vessel were added to the first reaction mixture, maintaining the temperature above 90 C. The combined reaction mixture was stirred for 2 hours, cooled to room temperature, and further stirred for 4 hours. Water (2.8 L) was added to the reaction mixture which was filtered. The obtained solid was crystallized in methanol to obtain a compound of Formula-B 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, 2-Bromo-8-fluoro-4,5-dihydro-1H-azepino[5,4,3-cd]indol-6(3H)-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MYLAN LABORATORIES LTD; JAYACHANDRA, Sureshbabu; SETHI, Madhuresh; KAUSHIK, Vipin Kumar; RAVI, Vijaya, Krishna; TELAGAMSETTY, Bhaskar Kumar; (44 pag.)WO2019/130229; (2019); 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. 830-43-3, name is 4-(Trifluoromethyl)benzenesulfonamide, This compound has unique chemical properties. The synthetic route is as follows., 830-43-3

Combine p-trifluoromethylbenzenesulfonamide (112.6 mg, 0.5 mmol), iridium catalyst (5.1 mg, 0.005 mmol, 1 mol%), potassium hydroxide (28 mg, 0.5 mmol, 1 equiv), and methanol (0.3 mL), water (0.9 mL) was sequentially added to the reaction vessel. After the reaction mixture was reacted at 130 C for 12 hours in a reaction vessel, it was cooled to room temperature. The solvent was removed by rotary evaporation, and then the purified target compound was obtained by column chromatography (developing solvent: petroleum ether / ethyl acetate), yield: 90%.

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; Nanjing University of Science and Technology; Meng Chong; Tang Yawen; Li Feng; (10 pag.)CN110857278; (2020); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

1103234-56-5, The chemical industry reduces the impact on the environment during synthesis 1103234-56-5, name is 2,6-Difluoro-3-(propylsulfonamido)benzoic acid, I believe this compound will play a more active role in future production and life.

2,6-Difluoro-3-(propylsulfonamido)benzoic acid (20.O g, 71.6 mmol) was dissolved in acetone (400 mL), and potassium carbonate (29.7 g, 215 mmol) was added. After stirring for 5 minutes, methyl iodide (13.4 mL, 215 mmol) was added. The reaction mixture was stirred overnight. The reaction mixture was filtered and the filtrate concentrated. The crude product was partitioned between ethyl acetate and water and the organic layer washed by brine, dried over MgSO4 and concentrated to dryness. Further removal of solvent under high vacuum afforded methyl 2,6-difluoro-3-(N-methylpropylsulfonamido)benzoate as light yellow solid (17.0 g, 77% yield). 1H NMR (500 MHz, CDCl3) delta 7.57 (td, IH), 7.10 – 6.89 (m, IH), 3.96 (s, 3H), 3.31 (s, 3H), 3.13 – 2.96 (m, 2H), 2.01 – 1.81 (m, 2H), 1.07 (t, 3H).

The chemical industry reduces the impact on the environment during synthesis 2,6-Difluoro-3-(propylsulfonamido)benzoic acid. I believe this compound will play a more active role in future production and life.

Reference:
Patent; ARRAY BIOPHARMA INC.; GENENTECH, INC.; ALIAGAS, Ignacio; GRADL, Stefan; GUNZNER, Janet; MATHIEU, Simon; RUDOLPH, Joachim; WEN, Zhaoyang; WENGLOWSKY, Steven Mark; WO2011/25947; (2011); A1;,
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177906-48-8, The chemical industry reduces the impact on the environment during synthesis 177906-48-8, name is trans-N-Boc-1,4-cyclohexanediamine, I believe this compound will play a more active role in future production and life.

[0311] To a stirred solution of 5-cyclopropyl-4-iodoisoxazole-3-carboxylic acid (1.0 g, 3.59 mmol) in DMF (10 ml) was added EDCI (0.892 g, 4.66 mmol) and HOBT (0.533 g, 3.94 mmol). The solution was stirred for 10 min at 0 C. Next tert-butyl ((lr,4r)-4- aminocyclohexyl)carbamate (0.769 g, 3.59 mmol) was added and the reaction was stirred at rt for 2hr. The progress of the reaction was monitored by TLC. After complete consumption of starting material, the reaction was quenched with water and the solid precipitated was collected by filtration and dried under reduced pressure to obtain a residue. The material was purified by column chromatography to afford tert-butyl ((lr,4r)-4-(5-cyclopropyl-4-iodoisoxazole-3-carboxamido)cyclohexyl)carbamate (0.48 g, 28 %).

The chemical industry reduces the impact on the environment during synthesis trans-N-Boc-1,4-cyclohexanediamine. I believe this compound will play a more active role in future production and life.

Reference:
Patent; EPIZYME, INC.; FOLEY, Megan Alene Cloonan; KUNTZ, Kevin Wayne; MILLS, James Edward John; MITCHELL, Lorna Helen; MUNCHHOF, Michael John; HARVEY, Darren Martin; (208 pag.)WO2016/40498; (2016); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

2886-65-9, 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. 2886-65-9, name is 7-Chloro-5-(2-fluorophenyl)-1H-benzo[e][1,4]diazepin-2(3H)-one, This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 1 7-Chloro-5-(2-fluorophenyl)-2-methylamino-3H-1,4-benzodiazepine A solution of 200 g. (0.695 m) of 7-chloro-1,3-dihydro-5-(2-fluorophenyl)-2H-1,4-benzodiazepin-2-one in 2 l. of tetrahydrofuran and 250 ml. of benzene was saturated with methylamine with cooling in an ice bath. A solution of 190 g. (1 m) of titaniumtetrachloride in 250 ml. of benzene was added through a dropping funnel within 15 minutes. After addition the mixture was stirred and refluxed for 3 hours. Water, 600 ml., was added slowly to the cooled reaction mixture. The inorganic material was separated by filtration and was washed well with tetrahydrofuran. The water layer was separated and the organic phase was dried over sodiumsulfate and evaporated. The crystalline residue was collected with m.p. 204-206. The analytical sample was recrystallized from methylene chloride/ethanol, m.p. 204-206.

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; Hoffmann-La Roche Inc.; US4280957; (1981); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Some common heterocyclic compound, 144-80-9, name is N-((4-Aminophenyl)sulfonyl)acetamide, molecular formula is C8H10N2O3S, 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. 144-80-9

General procedure: 5.1.2.1. General procedure. A mixture of 2 (1.88 g, 0.01 mol) and sulfa-drugs (0.012 mol) in absolute ethanol (10 mL) and glacial acetic acid (5 mL) was refluxed for 21 h, then left to cool. The solid product formed was collected by filtration and recrystallized from ethanol-dimethylformamide to give 3-20.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 144-80-9, its application will become more common.

Reference:
Article; Ghorab, Mostafa M.; Alsaid, Mansour S.; Al-Ansary, Ghada H.; Abdel-Latif, Ghada A.; Abou El Ella, Dalal A.; European Journal of Medicinal Chemistry; vol. 124; (2016); p. 946 – 958;,
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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. 239074-29-4, name is tert-Butyl (trans-4-(hydroxymethyl)cyclohexyl)carbamate, A new synthetic method of this compound is introduced below., 239074-29-4

To a solution of tert-butyl [trans-4-(hydroxymethyl)cyclohexyl]carbamate (0.50 g, 2.2 mmol) (Supplier: Chem-Impex) in methylene chloride (15 mL) was added triethylamine (1.29 mL, 9.27 mmol), 4-dimethylaminopyridine (53 mg, 0.44 mmol), and p-toluenesulfonyl chloride (0.89 g, 4.7 mmol). The resulting mixture was stirred at room temperature for 2 h before adding more p-toluenesulfonyl chloride (0.42 g, 2.2 mmol). The mixture was stirred overnight. Water and dichloromethane were added and the layers separated. The aqueous was extracted with dichloromethane. The combined organics were washed with water and brine, dried (MgSO4), filtered, and concentrated. The residue was purified on Biotage Isolera (40 g Agela cartridge, eluted with 5-50% EtOAc/hexanes over 15 min) to give the desired product (0.72 g, 86%) as a white crystalline solid. LCMS calculated for C19H29NO5SNa (M+Na)+: m/z=406.2. Found: 406.0.

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; Incyte Corporation; Li, Yun-Long; Zhu, Wenyu; Mei, Song; Glenn, Joseph; US2014/121198; (2014); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

621-38-5, 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 621-38-5 as follows.

Example 43-chloro -2 the same-acetamido […] synthesis ofTo 10 ml reaction flask by adding 3-bromo(acetylaniline) (0.2mmol, 42 . 81 mg), palladium acetate (0.002mmol, 0 . 45 mg), 3- chloroiodobenzene (0.22mmol, 52 . 46 mg), K3PO4(0.6mmol, 127 . 36 mg), silver acetate (0.3mmol, 50 . 07 mg), TFA (0.1mmol) and DCE (2 ml), for 90 C reaction under the conditions, the TLC reaction monitoring, when the temperature is reduced to the room temperature, adding phenylo boric acid (1.2mmol, 29 . 26 mg) with the ligand two phenol (0.004mmol, 1 . 07 mg), 80 C to continue reaction, the end point of the detection reaction TLC. When the reaction to room temperature, add 5 ml ethyl ether, the reaction solution is poured into the separatory funnel, using 5 ml ethyl ether washing reaction bottle, and then merged into the separatory funnel in ethyl ether, is added to the separatory funnel in 10 ml saturated NaCl solution, oscillating, liquid, so then to 10 ml ¡Á 2 of ethyl ether extraction, combined with the phase, adding anhydrous sodium sulfate for drying, filtering, vacuum screwed out of the solvent, with petroleum ether and ethyl acetate 3:1(v/v) as the mobile phase, rapid column separation, get the pure product white solid 3-chloro -2 the three-acetamido […] biphenyl, yield 86.5%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 621-38-5, and friends who are interested can also refer to it.

Reference:
Patent; Heilongjiang University; Chu, Wenyi; Ren, Limin; Sun, Zhizhong; Guan, Dinghui; Han, Lu; Wang, Lulu; Shi, Yang; (10 pag.)CN104003895; (2016); B;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

A common heterocyclic compound, 636-76-0, name is 3-Sulfamoylbenzoic acid, molecular formula is C7H7NO4S, 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. 636-76-0.

General procedure: A solution of 2-(2-methyl-1H-indol-1-yl)ethanamine (4a) (65 mg, 0.373 mmol) and 4-(piperidin-1-yl)benzoic acid (5) (76 mg, 1 eq.), and dimethylaminopyridine (catalytic, ?5 mg) in dichloromethane (6 mL) was added 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide.hydrochloride (EDCI) (92 mg, 1.3 eq.) at room temperature. The resulting reaction mixture was stirred for 6h. At the conclusion of the reaction (TLC), water (15 mL) was added to quench the reaction. The product was extracted with ethyl acetate (20mL¡Á3). Organics were washed with dilute HCl (10 mL), saturated NaHCO3 solution (10 mL), water (10 mL) and brine solution (10 mL) and dried over Na2SO4 and concentrated. The resulting crude product was subjected to silica gel chromatography eluting with 0-40% ethyl acetate in hexane to furnish 7k (TG7-152) (100mg, 74% yield). 1H NMR (CDCl3): delta 7.52 (d, J=5.6Hz, 1H), 7.49 (d, J=8.8Hz, 2H), 7.30 (d, J=8Hz, 1H), 7.07 (m, 2H), 6.80 (d, J=8.2Hz, 2H), 6.23 (s, 1H), 5.98 (t, J=5.4Hz, 1H), 4.33 (t, J=6Hz, 2H), 3.76 (q, J=6Hz, 2H), 3.25 (t, J=4.8Hz, 4H), 2.37 (s, 3H), 1.6 (m, 6H). LCMS (ESI): >97% purity at lambda 254, MS; m/z, 362 [M+H]+. Anal. Calcd. for C23H27N3O: C, 76.42; H, 7.53; N, 11.62; found; C, 76.48; H, 7.55; N, 11.59.

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

Reference:
Article; Ganesh, Thota; Jiang, Jianxiong; Dingledine, Ray; European Journal of Medicinal Chemistry; vol. 82; (2014); p. 521 – 535;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics