Tag: M.W=200-300

Synthetic Route of 1259224-00-4, 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. 1259224-00-4, name is tert-Butyl (1-(4-aminophenyl)cyclobutyl)carbamate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 2-chloro-3-(2-phenylethynyl)pyridine (426 mg, 2 mmol),Pd2(dba)3 (90 mg, 0.1 mmol), X-phos (190 mg, 0.4 mmol) and Cs2C03 (978 mg, 3 mmol) in Dioxane (8mL) was added tert-butyl l-(4-aminophenyl)cyclobutylcarbamate (524 mg, 2 mmol). The mixture degassed and charged with N2 for three times. And then the resulting mixture was stirred at 120 C for 60min by microwave irradiation. The reaction mixture was filtered by filter paper. The filtrate was concentrated under reduced pressure to get crude product, which was purified by flush column chromatography on silica gel (eluting with petroleum ether/ethyl acetate=l 00/1 -1/1) to yield the desired product tert-butyl l-(4-(3-(2-phenylethynyl)pyridin-2- ylamino)phenyl)cyclobutylcarbamate (220 mg, 25% yield^HNMR: MeOD 400MHz ? 8.08(s, lH), 7.71~7.69(d, 1H, J=8), 7.57~7.53(m, 4H), 7.38-7.36 (m, 5H), 6.75 (s, lH), 2.80-2.76 (m, 4H), 2.15-2.00 (m, 1H), 1.95-1.82 (m, 1H), 1.36 (s, 9H).

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 (1-(4-aminophenyl)cyclobutyl)carbamate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ARRAY BIOPHARMA INC.; GENENTECH, INC.; SKELTON, Nicholas; GRADL, Stefan; BLAKE, James F.; GRAHAM, James M.; GUNAWARDANA, Indrani W.; HENTEMANN, Martin; MARLOW, Allison L.; TANG, Tony P.; WO2013/78254; (2013); 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. 108468-00-4, name is 1-(N-Boc-aminomethyl)-4-(aminomethyl)benzene, A new synthetic method of this compound is introduced below., Recommanded Product: 108468-00-4

HOBT (1.45 g, 10.9 mmol) is added to a solution of {3-[3-(3-carboxymethoxyprop-1-ynyl)phenyl]prop-2-ynyloxy}acetic acid (A30, 0.40 g, 1.3 mmol) and 4-N-tert-butoxycarbonylaminomethylbenzylamine (1.2 g, 5.2 mmol) in absolute CH2Cl2 (20 ml) and Et3N (2.5 ml), and the mixture is stirred at RT for 45 min. EDC (2.1 g, 10.9 mmol) is then added, and the mixture is stirred at RT overnight. The reaction solution is diluted with CH2Cl2 (15 ml) and extracted (2¡Á) with semisaturated aqueous NH4Cl solution (25 ml), dried over MgSO4, filtered off and concentrated under reduced pressure. Further purification by chromatography [Tol/Ac (8:2)] over a silica gel column gives the title compound (1.1 g) as a colorless powder. TLC, silica gel, glass plates, [Tol/Ac (7:3)], Rf=0.51.MS: calc.: C42H50N4O8 (738.0), found: [MH+] 738.8, [MNH4+] 755.8; [MNa+] 761.2

The synthetic route of 108468-00-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Altana Pharma AG; US6960588; (2005); B1;,
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Synthetic Route of 141449-85-6,Some common heterocyclic compound, 141449-85-6, name is tert-Butyl hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate, molecular formula is C11H20N2O2, 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.

Reference Example 35: 5-(4-ChIoro-6-morphoIin-4-vI-pyrimidin-2-vImethyl)- hexahydro-pyrroloP.lambda-cipyrrole^-carboxylic acid tert- butyl ester; To a solution of 4-(2-bromomethyl-6-chloro-pyrimidin-4-yl)-morpholine (230 mg,0.786 mmol) in DMF (10 mL) were added potassium carbonate (212 mg, 1.53 mmol) and hexahydro-pyrrolo[3,4-c]pyrrole-2-carboxylic acid tert-butyl ester (250 mg, 1.18 mmol). The mixture was stirred at RT for 30 min. The reaction mixture was diluted with water then extracted into EtOAc. The organic layer was washed with brine, dried (MgSO4) and concentrated in vacuo. The resultant residue was purified by column chromatography to give the title compound as a colourless oil (332 mg, 100 %). [M + H]+ 424.3

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 hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate, its application will become more common.

Reference:
Patent; PIRAMED LIMITED; THE INSTITUTE OF CANCER RESEARCH; WO2008/125833; (2008); A1;,
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Application of 94838-59-2, These common heterocyclic compound, 94838-59-2, name is tert-Butyl 4-aminophenethylcarbamate, 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.

A mixture of 3-(4-methylpiperazin-l-yl)propanoic acid (172 mg, 1 mmol), HATU (456 mg, 1.2 mmol), DIPEA (323 mg, 2.5 mmol) and /ert-butyl 4-aminophenethylcarbamate (236 mg, 1 mmol) in DCM (10 mL) was stirred at room temperature overnight. TLC showed the reaction completed. The reaction mixture was concentrated and purified by column chromatography to afford the title compound as yellow solid (90mg, 23.0% yield). NMR (500 MHz, DMSO-riri) S: 10.01 (s, 1H), 7.48 (d, J= 8.4 Hz, 2H), 7.10 (d, J= 8.4 Hz, 2H), 6.84 (dd, J= 13.1, 6.9 Hz, 1H), 3.10 (dd, J= 14.1, 6.4 Hz, 2H), 2.64 (dd, .7= 24.9, 17.1 Hz, 6H), 2.45 (dd, J= 15.8, 8.8 Hz, 8H), 2.20 (d, J= 12.1 Hz, 3H), 1.37 (d, J= 1.6 Hz, 9H).

The synthetic route of 94838-59-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ZHEJIANG VIMGREEN PHARMACEUTICALS, LTD; SUN, Sanxing; ZHAO, Long; HU, Chongbo; CHEN, Zhengshu; YE, Jinqi; (0 pag.)WO2020/2969; (2020); A1;,
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Application of 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.

Sodium hydride (7.2 g, 0.3 mol) was weighed in a three-necked flask,Add 200 ml of tetrahydrofuran, cool to 0 or less,BOC-NH-PEG4 (29.3 g, 0.1 mol) was slowly added dropwise,Control the reaction temperature is about 0 . After 1 hour, continue to cool to -5 ,Slowly dropwise 3-bromopropionic acid (15.3 g, 0.1 mol) was added to control the reaction below 0 ,After the completion of the reaction at room temperature for 24 hours, with dilute hydrochloric acid PH value of 3-4,Ethyl acetate was extracted three times, the combined extracts were dried,Boc-NH-PEG4-CH2CH2COOH (23 g yield 63%) was recovered under reduced pressure.Boc-NH-PEG4-CH2CH2COOH (7.3 g, 0.020 mol) was dissolved in 50 mL of tetrahydrofuran,Slowly add 2mol / L hydrochloric acid solution (20mL),And stirred at room temperature overnight. The next day, add 50mL of ethyl acetate,And then extracted with ethyl acetate water phase once,The water phase evaporated to dry NH2PEG4-CH2CH2COOH hydrochloride crude,And then crystallized from ethyl acetate to give pale yellow crystals(3.92 g, Yield: 65%)

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; Chengdu Furuikang Biological Technology Co., Ltd.; Luo Qiandong; Hu Deyin; (7 pag.)CN104774161; (2017); B;,
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Some common heterocyclic compound, 1092522-02-5, name is tert-Butyl (4-aminophenyl)(methyl)carbamate, molecular formula is C12H18N2O2, 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. HPLC of Formula: C12H18N2O2

General procedure: HBTU (1.82g, 3.59mmol), DIPEA (0.84mL, 4.80mmol) and monomethyl suberate (0.93mL, 5.28mmol) were added to a solution of 34 (1.0g, 4.80mmol) in DMF (10mL) and the mixture was stirred for 12hat rt. Then the reaction was quenched with H2O and extracted using EtOAc, dried over MgSO4 and passed through a filter column to give corresponding ester which was dissolved in the minimum amount of dioxane. H2O with pH adjusted to 3 using 3N HCl was added and the reaction mixture was stirred at reflux overnight to yield the corresponding free amine. The reaction was basified and extracted using EtOAc, then dried, concentrated and passed through a filter column to give the free amine. To a solution of this free amine (1.0g, 3.59mmol) in DMF (10mL) was added HBTU (1.36g, 3.59mmol), DIPEA (0.66mL, 3.59mmol) and 1,4-dibenzyloxy-5-isopropyl benzoic acid (0.76g, 4.31mmol) and the solution was stirred for 12hat 80C. The reaction mixture was quenched with H2O and extracted with EtOAc (25mL¡Á3). The combined organic layer was collected, dried over anhydrous MgSO4 and concentrated under reduced pressure to give a light yellow residue, which was purified by silica gel chromatography (EtOAc:n-hexane=1: 1) to give 42 as a colorless liquid in 65% yield (overall from 34)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1092522-02-5, its application will become more common.

Reference:
Article; Mehndiratta, Samir; Lin, Mei-Hsiang; Wu, Yi-Wen; Chen, Chun-Han; Wu, Tung-Yun; Chuang, Kuo-Hsiang; Chao, Min-Wu; Chen, Yi-Ying; Pan, Shiow-Lin; Chen, Mei-Chuan; Liou, Jing-Ping; European Journal of Medicinal Chemistry; vol. 185; (2020);,
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Application of 97-35-8,Some common heterocyclic compound, 97-35-8, name is 3-Amino-N,N-diethyl-4-methoxybenzenesulfonamide, molecular formula is C11H18N2O3S, 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.

Step 1 Production of 3-amino-N,N-diethyl-4-hydroxybenzenesulfonamide 3-Amino-N,N-diethyl-4-methoxybenzenesulfonamide (5 g) was dissolved in methylene chloride (150 mL). Under ice-cooling, boron tribromide (1.0 M methylene chloride solution, 38.7 mL) was added dropwise, and the mixture was stirred overnight at room temperature. Water (150 mL) was added dropwise to the reaction mixture under ice-cooling, and the aqueous layer was washed with chloroform. The obtained aqueous layer was weak acidified with 4N aqueous sodium hydroxide under ice-cooling. The precipitated solid was collected by filtration to give the title compound (4.0344 g) as a pale-beige solid.

The synthetic route of 97-35-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Japan Tobacco Inc.; US2008/64871; (2008); A1;,
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Adding a certain compound to certain chemical reactions, such as: 138-41-0, name is Carzenide, 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 138-41-0, Application In Synthesis of Carzenide

Tolylsulfonamide 10 (1.00mM) was first converted to 4-aminosulfonyl benzoic acid by refluxing its aqueous suspension with KMnO4 (3.00mM) to generate the corresponding carboxylic acid followed by refluxing its methanolic solution firstly in acidic condition and then in excess of hydrazine hydrate.37 Yield 74%, lit. mp: 230-232C, Obs. mp: 228-230C.

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, Carzenide, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Sitaram; Celik, Gulsah; Khloya, Poonam; Vullo, Daniela; Supuran, Claudiu T.; Sharma, Pawan K.; Bioorganic and Medicinal Chemistry; vol. 22; 6; (2014); p. 1873 – 1882;,
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Reference of 54616-47-6, A common heterocyclic compound, 54616-47-6, name is 2-Bromo-N,N-dimethylbenzamide, molecular formula is C9H10BrNO, 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.

General procedure: To a stirred solution of 1 (0.23 g, 1.0 mmol) in THF (6 mL) at -78C was added n-BuLi (1.6 M in hexane; 1.0 mmol) dropwise. After 15 min, PhNCS(0.14 g, 1.0 mmol) was added and stirring was continued for an additional 5 min before addition of saturated aqueous NH4Cl (15 mL). The mixture was extracted with AcOEt (3 ¡Á 10 mL), and the combined extracts were washed with brine (10 mL), dried (Na2SO4) and concentrated by evaporation

The synthetic route of 54616-47-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kobayashi, Kazuhiro; Shigemura, Yuuho; Fujiwara, Daiki; Heterocycles; vol. 94; 6; (2017); p. 1152 – 1158;,
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Reference of 35303-76-5, 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 35303-76-5 as follows.

4-(2-aminoethyl)benzenesulfonamide (0.86 mmol) was added to a THF solution (20 ml) of 1- (3-isocyanatopropyl) -4-methoxybenzene Gt; min. & Lt; / RTI & gt; The reaction mixture was stirred at 40-45¡ã C for 24 hours. The next day, TLC was used to confirm the termination of the reaction. The solvent was distilled off and ammonium chloride (100 ml), 1N HCl solution (50 ml) and ethyl acetate (100 ml) were added to the remaining residue. The organic layer was washed with brine and dried over sodium sulfate. The solvent was distilled off and the residue was adsorbed onto silica gel using methylene chloride. The title compound was then separated and purified by column chromatography using ethyl acetate and hexane

According to the analysis of related databases, 35303-76-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CHUNGNAM NATIONAL UNIVERSITY INDUSTRY & ACADEMIC COOPERATION (IAC); JUNG, SANG HUN; WOO, SUN HEE; KIM, SANG KYUM; JEON, EUN SEOK; LEE, YOU JUNG; MANICKAM, MANOJ; JALANI HITESHKUMAR, HITESHKUMAR; SHARMA, NITI; (234 pag.)KR2015/111825; (2015); A;,
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