Tag: M.W=200-300

106984-09-2, A common heterocyclic compound, 106984-09-2, name is tert-Butyl (2-(2-(2-(2-hydroxyethoxy)ethoxy)ethoxy)ethyl)carbamate, molecular formula is C13H27NO6, 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.

Into a 50-mL round-bottom flask, was placed a solution of tert-butyl N-(2-[2-[2-(2-hydroxyethoxy)ethoxy]ethoxy]ethyl)carbamate (300.0 mg, 1.02 mmol, 1.00 equiv) in tetrahydrofuran (10 mL), sodium hydride (50.0 mg, 2.08 mmol, 1.20 equiv), 2-bromoacetic acid (141.0 mg, 1.01 mmol, 1.00 equiv). The resulting solution was stirred for 4 h at room temperature. The reaction was then quenched by the addition of water (20 mL). The resulting solution was extracted with ethyl acetate (20 mL*3). The combined organic layers were washed with brine (20 mL*1). The resulting mixture was concentrated under vacuum. This resulted in 310.0 mg (86%) of 14-[[(tert-butoxy)carbonyl]amino]-3,6,9,12-tetraoxatetradecanoic acid as light yellow oil.

The synthetic route of tert-Butyl (2-(2-(2-(2-hydroxyethoxy)ethoxy)ethoxy)ethyl)carbamate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Arvinas, Inc.; Crew, Andrew P.; Crews, Craig M.; Dong, Hanqing; Qian, Yimin; Wang, Jing; (104 pag.)US2017/8904; (2017); A1;,
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4093-29-2, A common heterocyclic compound, 4093-29-2, name is Methyl 4-acetamido-2-methoxybenzoate, molecular formula is C11H13NO4, 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.

To a 3-neck flask equipped with a mechanical stirrer was charged 250 g (1.12 mol) of 2-methoxy-4-acetylaminobenzoic acid methyl ester followed by 1L of methanol. Agitation was started and 94 mL (3.36 mmol, 3 eq. ) of concentrated sulfuric acid was slowly added creating a slight reflux. The mixture was stirred for 24 hr. The mixture was concentrated in vacuo affording a thick slurry. The slurry was filtered using a Buchner funnel and washed with 300 mL of cold methanol. The filter cake was collected and dried in vacuo at 45 C for 24 hr affording 302 g of 1a as a hemi-sulfate salt in a 96% yield.

The synthetic route of Methyl 4-acetamido-2-methoxybenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SB PHARMCO PUERTO RICO INC; NEUROCRINE BIOSCIENCES INC; WO2005/63755; (2005); A1;,
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106984-09-2, 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. 106984-09-2, name is tert-Butyl (2-(2-(2-(2-hydroxyethoxy)ethoxy)ethoxy)ethyl)carbamate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of tert-butyl (2-(2-(2-(2-hydroxyethoxy)ethoxy)ethoxy)ethyl)carbamate (10.0 g, 34.1 mmol, Step 1 of Intermediate EN) in anhydrous THF (250 mL) was added sodium hydride (1.63 g, 40.94 mmol, 60% dispersion in mineral oil) in one portion under nitrogen atmosphere. The reaction mixture was stirred at rt for 0.5 h and thereafter it was cooled to 0 C. An 80% solution of 3-bromoprop-1-yne in toluene (5.7 mL, 51.2 mmol) was added dropwise to the reaction mixture at 0 C. over a period of 10 min. The resulting reaction mixture was stirred at 0 C. for 1 h and thereafter it was allowed to warm to rt. The resulting reaction mixture was stirred overnight at rt. Then the reaction mixture was quenched with a small aliquot of methanol (1.6 mL) and concentrated on a rotary evaporator. The obtained crude material was suspended in DCM (100 mL) and was washed with water (2¡Á30 mL) and brine (50 mL). The resulting organic layer was dried over anhydrous sodium sulphate, filtered and concentrated on a rotary evaporator. The obtained crude product was purified by silica gel chromatography (gradient Ethyl acetate/Hexanes) to give the title compound (6.25 g, 55%) as a light yellow viscous liquid.

The synthetic route of 106984-09-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kymera Therapeutics, Inc.; Mainolfi, Nello; Ji, Nan; Kluge, Arthur F.; Weiss, Matthew M.; Zhang, Yi; (1443 pag.)US2019/192668; (2019); A1;,
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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. 621-38-5, name is 3-Bromoacetanilide, A new synthetic method of this compound is introduced below., 621-38-5

Embodiment 24-methyl -2 the same-acetamido […] synthesis ofTo 10 ml reaction flask by adding 3-polybromide monoacetylaniline (0.2mmol, 42 . 81 mg), palladium acetate (0.002mmol, 0 . 45 mg), 4-methyl iodophenylamino (0.22mmol, 47 . 97 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 4:1(v/v) as the mobile phase, rapid column separation, get the pure product white solid 4-methyl -2 the three-acetamido […] biphenyl, yield 94.0%.

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; Heilongjiang University; Chu, Wenyi; Ren, Limin; Sun, Zhizhong; Guan, Dinghui; Han, Lu; Wang, Lulu; Shi, Yang; (10 pag.)CN104003895; (2016); B;,
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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 127-77-5 as follows. 127-77-5

General procedure: To a solution of the amine 3a-l (1 eq) in anhydrous THF (30 mL/mmol) was added4-nitrophenylisocyanate (1 eq). The reaction mixture was stirred at room temperatureovernight, concentrated. Silica cake was prepared in acetone and chromatographicseparation on silica gel (EtOAc/CH2Cl2 = 1/30 to 1/5) gave the expected compound as asolid. Compounds 4e, 4f, 4h and 4l were further recrystallized in acetone to achieve desiredpurity but with substantially lower yields.

According to the analysis of related databases, 127-77-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Wang, Xu; Ahn, Yong-Mo; Lentscher, Adam G.; Lister, Julia S.; Brothers, Robert C.; Kneen, Malea M.; Gerratana, Barbara; Boshoff, Helena I.; Dowd, Cynthia S.; Bioorganic and Medicinal Chemistry Letters; vol. 27; 18; (2017); p. 4426 – 4430;,
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109903-35-7, name is 4-Amino-N-methylbenzenemethanesulfonamide, 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. 109903-35-7

EXAMPLE 48 2,6-Dibromo-4-methylaminosulfonylmethylaniline To a stirred solution of 4-methylaminosulfonylmethylaniline (10 g) in a mixture of methylene chloride (100 mL) and methanol (200 mL) was added sodium bicarbonate (12.6 g) followed by bromine (16 g) in methylene chloride (80 mL). Then the reaction mixture was evaporated in vacuo and the residue partitioned between ethyl acetate (200 mL) and water (100 mL). The ethyl acetate phase was washed with water and brine then dried and evaporated to give the title compound as a brown solid (17.1 g). mp 155-157 C. 1 H NMR (CDCL3) delta7.4 (s, 2H), 4.6 (bs, 2H), 4.1 (m, 3H), 2.75 (d, 3H).

Statistics shows that 109903-35-7 is playing an increasingly important role. we look forward to future research findings about 4-Amino-N-methylbenzenemethanesulfonamide.

Reference:
Patent; Pfizer Inc; US5607951; (1997); A;,
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A common heterocyclic compound, 6292-59-7, name is 4-(tert-Butyl)benzenesulfonamide, molecular formula is C10H15NO2S, 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. 6292-59-7.

A mixture of 4-teritary butyl benzene sulfonamide (15.2 grams) having 0.11percent of 4-isopropyl benzene sulfonamide, potassium carbonate (19.77 grams), tetrabutylammonium bromide (0.7 grams) in toluene (750 ml) was heated to 45-50¡ãC and stirred for 30 minutes.4,6-dichloro-5-(2-methoxyphenoxy)-2,2′-bipyrimidine (25 grams) was added the above mixture and heated to reflux temperature then stirred for 12 hours. The reaction mixture was cooled and then quenched with water. The reaction mixture was filtered and washed the solid with water. Acetonitrile (300 ml) was added to wet solid and heated to reflux temperature then stirred for 2 hours. Water (50 ml) was added to the above wet solid and acidified with hydrochloric acid. The solid was filtered, washed with water and dried to get the title compound.Yield: 80 grams; Purity by HPLC: 98.97 percent; isopropyl derivative: 0.11percent

The synthetic route of 4-(tert-Butyl)benzenesulfonamide has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MSN LABORATORIES LIMITED; SATYANARAYANA REDDY, Manne; ESWARAIAH, Sajja; VENKAT REDDY, Ghojala; WO2011/21216; (2011); A2;,
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127828-22-2, 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. 127828-22-2, name is tert-Butyl (2-(2-aminoethoxy)ethyl)carbamate, This compound has unique chemical properties. The synthetic route is as follows.

6.3g of compd 42 and 2.Og of 2-bromohypoxanthine were dispersed in 55ml monomethoxyethanol and 17.5ml water. The reaction mixture was stirred at reflux for 16h, and the solvent was removed under reduced pressure. Then the concentrate was stirred in 20ml MC and 10ml water for 30 min, and the resulting precipitate was collected by filtration to obtain 2.1g of compd 43 as a pale yellow solid. 1H NMR (500MHz; DMSOd6) delta 12.43 (br s, IH), 10.45 (br s, IH), 7.89 (s, 0.2H), 7.61 (s, 0.8H), 6.77 (m, IH), 6.34 (s, 0.8H), 6.12 (s, 0.2H), 3.52 (t, 2H), 3.41 (m, 4H), 3.09 (q, 2H), 1.36 (s, 9H).

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; CTI BIO; WO2009/113828; (2009); A2;,
Amide – Wikipedia,
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127-77-5, 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. 127-77-5, name is 4-Amino-N-phenylbenzenesulfonamide, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a solution of 4-chloro-2-(chlorocarbonyl)phenyl benzoate (1 mmol, 1.4 equiv) in DCM (0.2 M), amine (0.7 mmol, 1 equiv) and triethylamine (0.6 mL, 1.2 mmol, 1.7 equiv) were added at 0 C. The mixture was stirred at room temperature (16 h) and extracted with DCM. The organic layer was washed with water and brine, dried (MgSO4), and the solvent was removed under vacuum. The residue was purified by flash column chromatography. (0025) Potassium carbonate (18 mg, 0.13 mmol, 1.2 equiv) was added to a solution of crude product from the previous step (0.11 mmol, 1.0 equiv) in 1:1 MeOH:1,4-dioxane (0.1 M). The reaction mixture was stirred at room temperature (2 h) and acidified with 1 N HCl, followed by extraction with EtOAc and DCM. The organic layer was washed with water and brine, dried (MgSO4), and the solvent was removed under vacuum. The residue was purified by column chromatography (1:19 MeOH:CHCl3), and recrystallized from Et2O/Hex.

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; Lee, Ill-Young; Gruber, Todd D.; Samuels, Amanda; Yun, Minhan; Nam, Bora; Kang, Minseo; Crowley, Kathryn; Winterroth, Benjamin; Boshoff, Helena I.; Barry III, Clifton E.; Bioorganic and Medicinal Chemistry; vol. 21; 1; (2013); p. 114 – 126;,
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The chemical industry reduces the impact on the environment during synthesis 118753-70-1, name is tert-Butyl bis(2-chloroethyl)carbamate, I believe this compound will play a more active role in future production and life. 118753-70-1

To a solution of tert-butyl bis(2-chloroethyl)carbamate (5.08 g) and 2-(3,4-dichlorophenyl)acetonitrile (3.00 g) in anhydrous DMF (50 mL), 60percent (w/w) sodium hydride in oil (1.935 g) was added at 0¡ãC, and the mixture was stirred overnight at 70¡ãC in a nitrogen atmosphere. The reaction mixture was diluted with a saturated aqueous solution of ammonium chloride, followed by extraction with ethyl acetate. The extract was washed with water and saturated brine, dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography (ethyl acetate/hexane) to obtain the title compound (3.41 g). MS, found: 254.9.

The chemical industry reduces the impact on the environment during synthesis 118753-70-1. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Takeda Pharmaceutical Company Limited; IMAMURA Keisuke; TOMITA Naoki; ITO Yoshiteru; ONO Koji; MAEZAKI Hironobu; NII Noriyuki; (123 pag.)EP3118200; (2017); A1;,
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