Tag: M.W=200-300

127828-22-2, Name is tert-Butyl (2-(2-aminoethoxy)ethyl)carbamate, 127828-22-2, 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.

To a solution of mono-Boc protected diamine linker (0.1 mmol, 1 eq) and Imatinib- COOH (54 mg, 0.1 mmol, 1 eq) in DMF (1 mL), COMU (43 mg, 1 mmol, 1 eq) and DIPEA (48 m L ) were added. The reaction mixture was stirred at room temperature for 1 hour, then quenched with ice cold water. Volatiles were removed in vacuum and the crude mixture was purified by preparative HPLC (METHOD 2). Fractions containing the desired product were evaporated under reduced pressure and the residue was dissolved in DCM (1 mL) and treated with a solution of anhydrous HCl in dioxane (4M, 1 mL). After 1 hour, volatiles were removed under reduced pressure and the residue was freeze dried in order to remove any excess of acid. Analytical data (HRMS) are provided in table V shown below.

Statistics shows that tert-Butyl (2-(2-aminoethoxy)ethyl)carbamate is playing an increasingly important role. we look forward to future research findings about 127828-22-2.

Reference:
Patent; UNIVERSITY OF DUNDEE; CIULLI, Alessio; TESTA, Andrea; HUGHES, Scott; BUTCHER, Steven Peter; (337 pag.)WO2019/238817; (2019); A1;,
Amide – Wikipedia,
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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. 42137-88-2, name is N,N-Bis(2-chloroethyl)-4-methylbenzenesulfonamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 42137-88-2

Example VII A solution of 29.6 parts of N,N-bis(2-chloroethyl)-4-methylbenzenesulfonamide and 14.9 parts of 4-fluoro-2-methylbenzeneacetonitrile in 90 parts of methylbenzene is added dropwise to a solution of 5.6 parts of lithium amide in 270 parts of methylbenzene at about 90 C. Upon completion, the whole is heated to reflux and stirred overnight at reflux temperature. The reaction mixture is cooled, poured onto water and the layers are separated. The organic phase is dried, filtered and evaporated. The residue is crystallized from 2-propanol, yielding 27 parts (72.6%) of 4-(4-fluoro-2-methylphenyl)-1-(4-methylphenylsulfonyl)-4-piperidinecarbonitrile.

The synthetic route of 42137-88-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Janssen Pharmaceutica N.V.; US4369184; (1983); A;,
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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. 239074-29-4, name is tert-Butyl (trans-4-(hydroxymethyl)cyclohexyl)carbamate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 239074-29-4

A solution of tert-butyl [trans-4-(hydroxymethyl)cyclohexyl]carbamate (from Aldrich, 0.61 g, 2.7 mmol) in methylene chloride (10 mL) at 0 C. was added Dess-Martin periodinane (1.35 g, 3.19 mmol). The resulting mixture was stirred at room temperature overnight. The reaction was quenched with aq. 1 N NaOH solution, extracted with dichloromethane. The combined organic layers were washed with water and brine, dried over MgSO4, and concentrated. The residue was purified on silica gel (eluting with 0 to 5% MeOH in dichloromethane) to give the desired product (0.3 g, 50%). LCMS calculated for C12H21NO3Na (M+Na)+: m/z=250.2. Found: 250.1.

The synthetic route of 239074-29-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Incyte Corporation; Li, Yun-Long; Zhu, Wenyu; Mei, Song; Glenn, Joseph; US2014/121198; (2014); A1;,
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Adding a certain compound to certain chemical reactions, such as: 118753-70-1, name is tert-Butyl bis(2-chloroethyl)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 118753-70-1, 118753-70-1

To a stirred solution of 2-(4-fluorophenyl)acetonitrile (3.2 g, 23.7 mmol) and ie/ -butyl bis(2-chloroethyl)carbamate (DM, 6.69 g, 23.7 mmol) in DMF (40 mL), NaH (60percent, 2.8 g, 71.1 mmol) was added and the reaction mixture was stirred at 60C for 16 h. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was quenched using water and extracted with EtOAc. The combined organic layer was washed with brine, dried over anhydrous Na2S04 and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography using 10percent EtOAc/hexane to afford compound DN (4.2 g, 58percent) as a thick oil.

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, tert-Butyl bis(2-chloroethyl)carbamate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; VPS-3, INC.; YATES, Christopher, M.; (397 pag.)WO2018/165520; (2018); A1;,
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112101-81-2, A common compound: 112101-81-2, name is R-5-(2-Aminopropyl)-2-methoxybenzenesulfonamide, 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.

7.0 g of recrystallised (-)-(R)-5-(2-(2-(2-ethoxyphenoxy) ethylamino)-1-propyl)-2- methoxybenzenesulphonamide hydrochloride (TH) from Example 3 is recrystallised from mixtures of methanol and ethanol. Analysis : Methanol to HPLC-composition of Quantity Yield HPLC-composition of ethanol the starting raw of solvent the product* ratio material* used 100 : 0 TH 95. 84 % 90 ml 5. 44 g TH 97. 77 % impurity (2) 0. 09 % (77. 7%) impurity (2) 0. 0 % impurity (3) 0. 0 % impurity (3) 0. 0 % impurity (4) 0. 24 % impurity (4) 0. 04 % impurity (5) 0. 05 % impurity (5) 0. 0 % impurity (6) 3. 73 % impurity (_) 2. 19 % 90 : 10 TH 95. 5 % 110 ml 5. 64 g TH 97. 53 % impurity (2) 0. 12 % (80. 6%) impurity (2) 0. 12 % impurity (3) 0. 0 % impurity (3) 0. 0 % impurity (4) 0. 31 % impurity (4) 0. 06 % impurity (2 0. 08 % impurity (5) 0. 00 % impurity (6) 3. 94 % impurity (6) 2. 41 % 70 : 30 TH 95. 9 % 160 ml 5. 70 g TH 99. 89 % impurity (2) 0. 12 % (81. 4%) impurity (2) 0. 0 % impurity (3) 0. 0 % impurity (3) 0. 0 % impurity 0. 31 % impurity (4) 0. 05 % impurity (5) 0. 08 % impurity (5) 0. 0 % impurity (6) 3. 49 % impurity (6) 0. 0 % 50 : 50 TH 99. 27 % 230 ml 5. 95g TH 99. 85 % impurity (2) 0. 15 % (85. 0%) impurity (2) 0. 0 % impurity (3) 0. 0 % impurity (3) 0. 0 % impurity (4) 0. 32 % impurity (4) 0. 06 % impurity (5) 0. 08 % impurity (5) 0. 0 % impurity (6) 0. 0% impurity 0. 0% 30 : 70 TH 99. 28 % 340ml 5. 98 g TH 99. 81 % impurity (2) 0. 17 % (85. 4%) impurity (2) 0. 02 % impurity (3) 0. 0 % impurity (3) 0. 0 % impurity (4) 0. 32 % impurity (4) 0. 08 % impurity (5) 0. 10 % impurity (5) 0. 0 % impurity (6) 0. 0 % impurity (6) 0. 0 % * impurity (2) = 5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide impurity (3) = 2-(2-ethoxyphenoxy) ethylbromide impurity N- (2- (2-ethoxyphenoxy) ethyl)-5- (2- (2- (2-ethoxyphenoxy) ethyl) amino)-1-propyl)-2-methoxybenzenesulphonamide impurity (5) = 5-(2-(bis-(2-(2-ethoxyphenoxy) ethyl) amino)-1-propyl)-2-methoxybenzenesulphonamide impurity (6) = 1,2-bis (2-ethoxyphenoxy) ethane (6)

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, R-5-(2-Aminopropyl)-2-methoxybenzenesulfonamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; LEK PHARMACEUTICALS D.D.; WO2005/63702; (2005); 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. 22227-26-5, name is 3,5-Bis(trifluoromethyl)benzamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 22227-26-5

General procedure: Benzamide (476 mg, 3.9 mmol) and benzaldehyde(203 mL, 2 mmol) were dissolved in dry DMF (8 mL).TMSCl (507 mL, 4mmol) was added as a catalyst and wasstirred at 50 ¡ãC for 18 h under nitrogen. Awhite precipitatewas formed with the addition of a few drops of water andwas purified by stirring with diethyl ether for 30 min. Theproduct was isolated using vacuum filtration. Yield 31percent

The synthetic route of 22227-26-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Clarke, Harriet J.; Van Rossom, Wim; Horton, Peter N.; Light, Mark E.; Gale, Philip A.; Supramolecular Chemistry; vol. 28; 1-2; (2016); p. 10 – 17;,
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These common heterocyclic compound, 621-38-5, name is 3-Bromoacetanilide, 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. 621-38-5

A. 2-Bromo-4-(1-oxoethylamino)-benzenesulfonyl chloride To 2-bromo-4-(1-oxoethylamino)-benzene (6.2 g, 29 mmol) was added chlorosulfonic acid (20 mL). The solution was heated at 57 C. for 3 hours, an additional 10 mL of chlorosulfonic acid was added and the solution was heated at 67 C. for 6 hours. The mixture was added dropwise to ice water and the heterogeneous mixture was extracted with ethyl acetate. The organic extract was washed once with brine, dried (magnesium sulfate) and evaporated. The residue was dissolved in ethyl acetate (50 mL) and the solution was filtered. The insoluble solid was rinsed twice with ethyl acetate and the combined filtrates were evaporated to afford 6.9 g (82%) of crude compound A as a brown foamy gum.

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 621-38-5.

Reference:
Patent; Bristol-Myers Squibb Co.; US5514696; (1996); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

A common heterocyclic compound, 141449-85-6, name is tert-Butyl hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate, molecular formula is C11H20N2O2, 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. 141449-85-6.

The 5 – chloro – 1, 6 – naphthyridine (0.93 g, 5 . 65 mmol), hexahydro-pyrrolo [3, 4 – c] pyrrole -2 (1 H) – formic acid tert-butyl ester (1.00 g, 4 . 71 mmol), three (dibenzylidene acetone) two palladium (0.43 g, 0 . 47 mmol), 2 – dicyclohexyl phosphorus – 2, 4, 6 – triisopropyl biphenyl (0.46 g, 0 . 94 mmol), sodium tertiary butyl alcohol (1.40 g, 14.1 mmol) and toluene (20 ml) are added to the 100 ml single-port in the bottle, under the protection of nitrogen, reaction temperature to 120 C reaction 36 hours. Stopping the reaction, the reaction solution is distilled under reduced pressure to remove the solvent after purification by silica gel column chromatography (petroleum ether/ethyl acetate (v/v)=1/1) to obtain the title compound (light yellow liquid, 1.15 g, 71.7%).

The synthetic route of tert-Butyl hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Jin Chuanfei; Zhang Yingjun; Xue Yaping; Lao Jinhua; Nie Biao; Xu Juan; (35 pag.)CN107759620; (2018); A;,
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459817-82-4, Adding some certain compound to certain chemical reactions, such as: 459817-82-4, name is tert-Butyl 1,2,3-oxathiazolidine-3-carboxylate 2,2-dioxide, 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 459817-82-4.

Step 1 : To an oven-dried flask containing 4,6-dichloro-2- (methylsulfanyl)pyrimidine (390 mg, 2.0 mmol) in anhydrous THF (7.5 mL) was added TMPMgCI LiCI (2.4 mL, 2.4 mmol; as a 1 M solution in THF) at r.t. After stirring for 30 min, tert-butyl 1 ,2,3-oxathiazolidine-3-carboxylate 2,2-dioxide (469 mg, 2.1 mmol) was added and the reaction was stirred for a further 1 h at r.t. To the mixture was added 1 M citric acid (7.5 mL) and EtOAc (7.5 mL) followed by vigorous stirring for 5 min. The organic layer concentrated to give tert-butyl N-{2- [4,6-dichloro-2-(methylsulfanyl)pyrimidin-5-yl]ethyl}.

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 459817-82-4.

Reference:
Patent; THOMAS HELLEDAYS STIFTELSE FOeR MEDICINSK FORSKNING; SCOBIE, Martin; WALLNER, Olov; KOOLMEISTER, Tobias; VALLIN, Karl Sven Axel; HENRIKSSON, Carl Martin; HOMAN, Evert; HELLEDAY, Thomas; JACQUES, Sylvain; DESROSES, Matthieu; JACQUES-CORDONNIER, Marie-Caroline; FISKESUND, Roland Julius Yu; (359 pag.)WO2015/187089; (2015); A1;,
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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. 88829-82-7, name is tert-Butyl (8-aminooctyl)carbamate, This compound has unique chemical properties. The synthetic route is as follows., 88829-82-7

To a solution of 5-((S)-l-cyclohexyl-2-((S)-l-((l S,3aR,6aS)-l-((S)-l-(cyclopropylamino)- l,2-dioxohexan-3-ylcarbamoyl)hexahydrocyclopenta[c]pyrrol-2(lH)-yl)-3,3-dimethyl-l-oxobutan- 2-ylamino)-2-oxoethylcarbamoyl)pyrazine-2-carboxylic acid (120 mg, 0.166 mmol) and tert-butyl 8- aminooctylcarbamate (40.6 mg, 0.166 mmol) in DMF (1 mL), DIEA (107 mg, 0.83 mmol), HATU (126 mg, 0.332 mmol) and HOAt (4.5 mg, 0.0332 mmol) were added at 0C. The reaction was stirred for 10 minutes. The reaction mixture was purified with HPLC to get tert-butyl 8-(5-((S)-l- cyclohexyl-2-((S)- 1 -(( 1 S,3 aR,6aS)- 1 -((S)- 1 -(cyclopropylamino)- 1 ,2-dioxohexan-3 – ylcarbamoyl)hexahydrocyclopenta[c]pyrrol-2(lH)-yl)-3,3-dimethyl-l-oxobutan-2-ylamino)-2- oxoethylcarbamoyl)pyrazine-2-carboxamido)octylcarbamate. The residue was dissolved in DCM (1 mL), and then TFA (1 mL) was added to the solution. The mixture was stirred at room temperature for 1 hour. The solvent was evaporated under vacuum to get the crude product N2-(8- aminooctyl)-N5-((S)-l-cyclohexyl-2-((S)-l-((l S,3aR,6aS)-l-((S)-l-(cyclopropylamino)-l,2- dioxohexan-3-ylcarbamoyl)hexahydrocyclopenta[c]pyrrol-2(lH)-yl)-3,3-dimethyl-l-oxobutan-2- ylamino)-2-oxoethyl)pyrazine-2, 5-dicarboxamide TFA salt (141 mg, 0.15 mmol, 90%) without any further purification. LC/MS m/z calculated for [M+H]+ 850.5, found 850.5.

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; DANA-FARBER CANCER INSTITUTE, INC.; PRESIDENT AND FELLOWS OF HARVARD COLLEGE; GRAY, Nathanael S.; ZHANG, Tinghu; YANG, Priscilla; DE WISPELAERE, Melissanne; DU, Guangyan; (144 pag.)WO2020/69125; (2020); A1;,
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