Category: amides-buliding-blocks

A common heterocyclic compound, 17193-28-1, name is 1-Amino-1-cyclopentanecarboxamide, molecular formula is C6H12N2O, 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. 17193-28-1.

To a solution of 1-aminocyclopentane-l-carboxamide (1.15 g, 8.97 mmol) and DCM (32 mL) was added acetic anhydride (1.191 g, 11.66 mmol). The reaction mixture was stirred at RT for 18 hours. Reaction was concentrated and used without further purification in the next step. Intermediate 110a (1.53 g, 8.99 mmol, 100 % yield). LC-MS (Method A2) RT = 0.43 min, MS (ESI) m/z: 171.1 (M+H)+. 1H NMR (400 MHz, CDCl3) delta 7.09 – 6.89 (m, 1H), 5.72 (br s, 1H), 5.38 – 5.19 (m, 1H), 2.40 – 2.30 (m, 2H), 2.07 – 1.98 (m, 5H), 1.86 – 1.75 (m, 4H)

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

Reference:
Patent; UNIVERSITE DE MONTREAL; BRISTOL-MYERS SQUIBB COMPANY; PRIESTLEY, Eldon, Scott; REZNIK, Samuel, Kaye; RUEDIGER, Edward, H.; GILLARD, James, R.; HALPERN, Oz, Scott; JIANG, Wen; RICHTER, Jeremy; RUEL, Rejean; TRIPATHY, Sasmita; YANG, Wu; ZHANG, Xiaojun; (642 pag.)WO2018/5591; (2018); A1;,
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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;,
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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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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. 1120-16-7 name is Dodecanamide, 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. 1120-16-7

General procedure: For the synthesis of amide carboxylic acid (1-2 mM) wasdissolved in toluene (10 ml) then solution of borane tetrahydrofuran(THF) (1 M) was added at 0 oC. After additionof borane THF complex reaction mixture is kept at roomtemperature for 1 h. DAA was added to the reaction mixtureand reaction mixture refluxed for 5-10 h. Then reactionmixture was cooled to room temperature and acidifies with1M HCl, and extracted with ethyl acetate. Wash with water2-3 times. Organic phase was dried over anhydrous Na2SO4and concentrate under reduced pressure. Purification ofproduct was accomplished by column chromatographyusing silica gel (hexane: ethyl acetate). (+)-N-(dodecanoyl)-dehydroabietylamine (2) Rf: 0.627(hexane/ethylacetate, 9:1) State: gummy, Yield:93.15%, [alpha]D26: -18.42 (C=0.0403, CHCl3), HRMS-ESI:calcd for C32H54NO (M+H)+ 468.4205, found 468.4179,IR (cm-1): 3303 (N-H stretching), 2923 (C-H), 2856(C-H),1647 (C=O), 1548 (N-H bending), 1460 (CH2 bending),1375 (CH3 bending), 719 (CH2 long chain band). UV: lambdamax241, 254, 276. 1HNMR (400MHz, CDCl3) delta ppm: 0.86(3H, t, J = 6.0 Hz, H-12?), 0.98 (3H, s, H-19), 1.23 (24H, Brs, H-16, and 17, 3?-11?), 1.95 (1H, t, J = 5.6 Hz, H-5), 2.32(4H, t, J = 7.6 Hz, H-1, and 2?), 2.86 (2H, m, H-3), 2.98(1H, m, H-15), 3.17 (1H, dd, J = 6.4 and 13.6 Hz, H-18a),3.28 (1H, dd, J = 6.4 and 13.6 Hz, H-18b), 7.28 (1H, d, J =8.0 Hz, H-12), 7.39 (1H, d, J = 8.0 Hz, H-11), 7.83 (1H, s,H-14). 13CNMR (100MHz, CDCl3) delta ppm: 14.1 (C-12?),18.5 (C-2), 18.7 (C-19), 18.9 (C-6), 22.6 (C-11?), 24.7 (C-16 and 17), 25.2 (C-20), 29.5-29.3 (C-3?-9?), 31.8 (C-10?),33.5 (C-15), 33.7 (C-2?), 35.7 (C-3), 37.3 (C-4), 37.4 (C-10), 38.3 (C-1), 44.5 (C-5), 49.7 (C-18), 123.6 (C-12),124.9 (C-11), 132.6 (C-14), 134.7 (C-8), 145.6 (C-13),147.1 (C-9), 173.5 (C-1?).

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

Reference:
Article; Mustufa, Muhammad Ayaz; Aslam, Afshan; Ozen, Cigdem; Ali Hashmi, Imran; Naqvi, Naim ul Hasan; Ozturk, Mehmet; Ali, Firdous Imran; Medicinal Chemistry Research; vol. 26; 7; (2017); p. 1367 – 1376;,
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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;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

These common heterocyclic compound, 106984-09-2, name is tert-Butyl (2-(2-(2-(2-hydroxyethoxy)ethoxy)ethoxy)ethyl)carbamate, 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. 106984-09-2

To a stirred solution of tert-butyl (2-(2-(2-(2-hydroxyethoxy)ethoxy)ethoxy)ethyl)carbamate (0.38 g, 1.29 mmol) and 2-bromoacetic acid (0.54 g, 3.8 mmol) in toluene:THF (1:1, 4 mL) was added NaOH (0.31 g, 7.7 mmol) at 45 C. The resulting reaction mixture stirred at 45 C. for 16 h. The reaction mixture was then evaporated, water (10 mL) was added and aqueous layer was acidified with 1 N HCl solution. The resulting mixture was extracted using DCM (3¡Á50 mL) and the combined organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was evaporated under reduced pressure to give 2,2-dimethyl-4-oxo-3,8,11,14,17-pentaoxa-5-azanonadecan-19-oic acid as a colorless oil (0.24 g, 53%). LC-MS (ESI+) m/z 351.4 (M+H)+.

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 106984-09-2.

Reference:
Patent; Kymera Therapeutics, Inc.; Mainolfi, Nello; Ji, Nan; Kluge, Arthur F.; Weiss, Matthew M.; Zhang, Yi; (1443 pag.)US2019/192668; (2019); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

144-80-9, 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. 144-80-9, name is N-((4-Aminophenyl)sulfonyl)acetamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A solution of 0.01 mol of methyl 4-(4-bromophenyl)-2,4-dioxobutanoate in 10 mL of glacial acetic acid was added to a solution of 0.01 mol of N-(4-aminobenzenesulfonyl)acetamide and 0.01 mol of benzaldehyde in 15 mL of glacial acetic acid. The mixture was refluxed for 3-5 min and cooled, and the precipitate was filtered off and recrystallized from dioxane [8]. Yield 4.33 g (78%).

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

Reference:
Article; Bobrovskaya; Gein; Seliverstov; Chashchina; Dmitriev; Russian Journal of General Chemistry; vol. 87; 12; (2017); p. 2776 – 2782; Zh. Obshch. Khim.; vol. 87; 12; (2017); p. 1957 – 1964,8;,
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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 67442-07-3 as follows. 67442-07-3

1. 2-Imidazol-1-yl-N-methoxy-N-methyl-acetamide 60percent sodium hydride in oil (0.296 g, 7.4 mol) was washed with tetrahydrofuran and suspended in additional tetrahydrofuran (10 ml). To this was added imidazole (0.506 g, 7.43 mol) followed by stirring at 25¡ã C. for 1 hour. To the mixture was added a solution of 2-chloro-N-methoxy-N-methyl-acetamide (1.02 g, 7.4 mmol, prepared per Tetrahedron Letters Vol. 30, No. 29, pp3779-80, 1989.) followed by stirring at 25¡ã C. for 15. The mixture was filtered, and the filtrate was evaporated to an oil in vacuo and purifide by chromatography on silica gel eluted with a gradient of chloroform to 10percent methanol:chloroform giving a solid 0.46 g, 37percent yield.

According to the analysis of related databases, 67442-07-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Denny, William Alexander; Hutchings, Richard H; Johnson, Douglas S; Kaltenbronn, James Stanely; Lee, Ho Huat; Leonard, Daniele Marie; Milbank, Jared Bruce John; Repine, Joseph Thomas; Rewcastle, Gordon William; White, Andrew David; US2004/44057; (2004); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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. 630-22-8 name is 2,2-Dimethylpropanethioamide, 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. 630-22-8

N-Bromosuccinimide (107mg, 0.60mmol) was added to a solution of tert-bv yl (3-(2-(2- chloropyrimidin-4-yl)acetyl)-2-fluorophenyl)carbamate (200. Omg, 0.54mmol) in dimethylacetamide (5.5mL). The reaction mixture was stirred at room temperature for lh then 2,2,2-Trimethylthioacetamide (70mg, 0.60mmol) was added. After stirring at room temperature for lh, the medium was heated at 50C overnight. The mixture was poured onto water and the suspension was filtered. The solid was dried under vacuum to afford the title (220mg, 86%). LC/MS (ES+): 463.3-465.3 (M+l).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2,2-Dimethylpropanethioamide, and friends who are interested can also refer to it.

Reference:
Patent; CELLIPSE; PRUDENT, Renaud; PAUBLANT, Fabrice; (74 pag.)WO2018/55097; (2018); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

402-46-0, Adding a certain compound to certain chemical reactions, such as: 402-46-0, name is 4-Fluorobenzenesulfonamide, 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 402-46-0.

General procedure: A solution of compound 9, 12a-12g or 16a-16g (1.0eq),substituted sulfonyl chloride (1.1eq) or substituted acyl chloride(1.1eq) and TEA(1.5eq) were added into DMF(5 ml. And then themixture was stirred at room temperature for 6 h. Upon completion,ethyl acetate (20 ml) and H2O (5 ml) were added. The aqueous layerwas extracted with ethyl acetate for several times, the combinedorganic layers were washed with H2O for several times, and thenwashed with brine, dried over MgSO4 and evaporated to give theproducts. The crude residue was purified by silica gel columnchromatography eluted with a mixture of petroleum ether andethyl acetate (2:1) to obtain target compound.

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; Jian-Song; Gao, Qiu-Lei; Wu, Bo-Wen; Li, Dong; Shi, Lei; Zhu, Ting; Lou, Jian-Feng; Jin, Cheng-Yun; Zhang, Yan-Bing; Zhang, Sai-Yang; Liu, Hong-Min; European Journal of Medicinal Chemistry; vol. 183; (2019);,
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Amide – an overview | ScienceDirect Topics