Author: Jessica.F

Synthetic Route of 5577-13-9, A common heterocyclic compound, 5577-13-9, name is Ethyl tosylcarbamate, molecular formula is C10H13NO4S, 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: A solution of ethyl (phenylsulfonyl) carbamate (1.2 mmol, 18a-d) in toluene (5 mL) was addeddropwise to a solution of 8a-d or 14a-d (1 mmol) in toluene (15 mL). Upon completion of the addition,the reaction mixture was stirred at 120 C for 6 h and monitored by thin-layer chromatography (TLC).The reaction mixture was cooled to room temperature and concentrated under a reduced pressure.Then, ethyl acetate was added and the insoluble materials were collected by filtration and driedto yield the target compounds 19a-d, 20a-d, 21a-d, 22a-d and 23a-d, which were recrystallizedfrom isopropanol.

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:
Article; Zhao, Bingbing; Lei, Fei; Wang, Caolin; Zhang, Binliang; Yang, Zunhua; Li, Wei; Zhu, Wufu; Xu, Shan; Molecules; vol. 23; 7; (2018);,
Amide – Wikipedia,
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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. 630-22-8, name is 2,2-Dimethylpropanethioamide, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 630-22-8

Example 23; N-[2-Chloro-3-(2-(1,1-dimethylethyl)-5-{2-[(2-methylpropyl)amino]-4-pyrimidinyl}-1,3-thiazol-4-yl)phenyl]-2,5-difluorobenzenesulfonamide; Step A: N-{2-Chloro-3-[5-(2-chloro-4-pyrimidinyl)-2-(1,1-dimethylethyl)-1,3-thiazol-4-yl]phenyl}-2,5-difluorobenzenesulfonamide; To a solution of N-{2-chloro-3-[(E)-2-(2-chloro-4-pyrimidinyl)-1-hydroxyethenyl]phenyl}-2,5-difluorobenzenesulfonamide (3.0 g, 6.55 mmol) in DMA (25 mL) was added NBS (1.165 g, 6.55 mmol). After stirring for 1 h at rt, 2,2-dimethylpropanethioamide (0.767 g, 6.55 mmol) was added and the reaction mixture was stirred at 80 C. for 2 h. The reaction mixture was diluted with EtOAc (100 mL) and extracted five times with water. The organic layer was dried over anhydrous NaSO4, adsorbed onto silica gel, and purified via column chromatography, eluting with 0-50% EtOAc/DCM. The desired fractions were combined and concentrated to generate 1.31 g (2.36 mmol, 36.0% yield) of the title compound as a yellow powder. 1H NMR (400 MHz, DMSO-d6): delta 10.74 (s, 1H), 8.56 (d, J=5.4 Hz, 1H), 7.41-7.58 (m, 6H), 6.57 (d, J=5.4 Hz, 1H), 1.42 (s, 9H). MS (ESI): 555.0 [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 630-22-8.

Reference:
Patent; Adams, Jerry Leroy; Dickerson, Scott Howard; Johnson, Neil W.; Kuntz, Kevin; Petrov, Kimberly; Ralph, Jeffrey M.; Rheault, Tara Renae; Schaaf, Gregory; Stellwagen, John; Tian, Xinrong; Uehling, David Edward; Waterson, Alex Gregory; Wilson, Brian; US2009/298815; (2009); A1;,
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Electric Literature of 6292-59-7, 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. 6292-59-7 name is 4-(tert-Butyl)benzenesulfonamide, 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.

Step-A: 4-tert-butyl-N-[6-chloro-5-(2-methoxyphenoxy)-2-(2-pyrimidinyl)-4-pyridinyl]benzene sulfonamide potassium salt (potassium salt of (IV)) 4,6 dichloro-5-(2-methoxybenzyl)-2,2-bipyrimidine (II) (100 g, 0.286 moles) and anisole (1250 ml) were placed in a reaction flask. Potassium carbonate (79 g, 0.572 moles) was added and reaction mass was stirred for 15 minutes. 4-tert-butylbenzenesulphonamide (III) (213 g, 0.286 moles) was added to reaction mass and heated to 140 C. for three hours. After completion of reaction the reaction mass was brought to room temperature and poured into purified water. The solid product was filtered off, washed with THF and dried to afford 4-tert-butyl-N-[6-chloro-5-(2-methoxyphenoxy)-2-(2-pyrimidinyl)-4-pyridinyl]benzene sulfonamide potassium salt. (161 g, yield 96.2% , purity by HPLC: 99.7%)

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-(tert-Butyl)benzenesulfonamide, and friends who are interested can also refer to it.

Reference:
Patent; Natco Pharma Limited; Kompella, Amala Kishan; Kasa, Srinivasu; Balina, Veera Swamy; Kusumba, Subhash; Adibhatla, Kali Satya Bhujanga Rao; Nannapaneni, Venkaiah Chowdary; US2013/245259; (2013); A1;,
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Related Products of 579474-47-8, 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. 579474-47-8, name is tert-Butyl 2-amino-4-fluorophenylcarbamate, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: 4-(8-Fluoro-2-oxo-2,3-dihydro-1H-benzo[b][1,4]diazepin-4-yl)picolinonitrile (1b). tert-Butyl (2-amino-4-fluorophenyl)carbamate (0.226g, 1mmol) and tert-butyl 3-(2-cyanopyridin-4-yl)-3-oxopropanoate (0.320g, 1.3mmol) were dissolved in toluene (5mL) and heated at reflux for 1h. The reaction mixture was cooled and the excess solvent was removed under reduced pressure. The crude intermediate was taken up in CH2Cl2 and TFA (1.14g, 10mmol) was added dropwise to it at 0C. The resulting reaction mixture was stirred at rt for 7h. The crude mixture was washed with sodium bicarbonate solution and the aqueous layer extracted with CH2Cl2. The combined organic layers were washed with water, then brine, and dried over Na2SO4. Evaporation of the solvent followed by column chromatography using hexanes:ethyl acetate (60:40) yielded the title compound.

The chemical industry reduces the impact on the environment during synthesis tert-Butyl 2-amino-4-fluorophenylcarbamate. I believe this compound will play a more active role in future production and life.

Reference:
Article; Dhanya, Raveendra Panickar; Herath, Ananda; Sheffler, Douglas J.; Cosford, Nicholas D.P.; Tetrahedron; vol. 74; 25; (2018); p. 3165 – 3170;,
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Synthetic Route of 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.

To a stirred solution of 2-(2,6-dioxopiperidin-3 -yl)-5-fluoroisoindoline- 1,3 -dione (3-1,100mg, 0.362mmo1, 1 equiv)inNMP(1.8mL, 0.2 M) was added DIPEA (126 jiL, 0.724mmol, 2 equiv) and tert-butyl (2-(2-aminoethoxy)ethyl)carbamate (74 mg, 0.362 mmol, 1 equiv). The reaction mixture was heated to 90 C overnight and then cooled to room temperature. EtOAc (50 mL) was added. The organic layer was washed with water (30 mL) and brine (3 x 30 mL), dried over Na2504, filtered, and concentrated in vacuo. The residue was purified by flashcolumn chromatography on silica gel (eluting with 0 to 5% MeOH in CH2C12) to give the title compound 9-1 as a yellow solid (37 mg, 22%). ?H NIVIR (500 MHz, CDC13) 8.70 (s, 1H), 7.607.47 (m, 1H), 6.99 – 6.85 (m, 1H), 6.74 (d, J= 8.3 Hz, 1H), 5.06 -4.96 (m, 1H), 4.92 (dd, J= 12.0, 5.3 Hz, 1H), 3.72 – 3.63 (m, 2H), 3.58 – 3.48 (m, 2H), 3.33 – 3.24 (m, 4H), 2.95 – 2.66 (m, 3H), 2.09 (ddd, J= 10.5, 6.6, 3.2 Hz, 1H), 1.43 (s, 9H). MS (ESI) [M+H]: 461.2.

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; DANA-FARBER CANCER INSTITUTE, INC.; BRADNER, James; BUCKLEY, Dennis; ISHOEY, Mette; WINTER, Georg; (195 pag.)WO2018/98280; (2018); A1;,
Amide – Wikipedia,
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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. 60144-53-8, name is tert-Butyl (4-fluorophenyl)carbamate, A new synthetic method of this compound is introduced below., Formula: C11H14FNO2

(4-Bromo-thiazol-2-yl)-(4-fluoro-phenyl)-carbamic acid tert-butyl ester; A mixture of (4-fluoro-phenyl)-carbamic acid tert-butyl ester (260 mg, 1.23 mmol), 2,4-dibromothiazole (100 mg, 0.41 mmol), copper powder (26 mg, 0.41 mmol), CuCl (41 mg, 0.41 mmol), and KOAc (40 mg, 0.41 mmol) in pyridine (4 ml) is heated at 1000C for 2 hours. The cooled mixture is diluted with EtOAc (30 ml) and washed with H2O (30 ml). The organic layer is dried over Na2SO4, filtered and concentrated in vacuum. The residue is purified by HPLC (C]8 column, eluted with CH3CN/H2O with 0.035% TFA) to give the title compound as solid: 1H NMR (DMSO-d6) delta 1.36 (s, 9H), 7.29 (t, 2H, J = 8.8 Hz), 7.37-7.43 (m, 3H); m/z [M+^t-Bu] 316.9.

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; IRM LLC; WO2007/16228; (2007); A2;,
Amide – Wikipedia,
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. 35303-76-5, name is 4-(2-Aminoethyl)benzenesulfonamide, This compound has unique chemical properties. The synthetic route is as follows., Safety of 4-(2-Aminoethyl)benzenesulfonamide

To a solution of 1- (3-isocyanatopropyl) -4-methoxybenzene (0.78 mmol) in THFWas added 4- (2-aminoethyl) benzenesulfonamide (0.86 mmol) at room temperature to a solution (20 ml)Was slowly added over 10-15 minutes. The reaction mixture was stirred at 40-45 [deg.] C for 24 hours. The next day TLC confirmed the termination of the reaction. The solvent was distilled off and ammonium chloride (100 & lt; RTI ID = 0.0 & gt;Ml), 1N HCl solution (50 ml) and ethyl acetate (100 ml). The organic layer was washed with brine and then dried with sodium sulfate. The solvent was distilled off and the residue was adsorbed onto silica gel using methylene chloride. The title compound was then 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; The Industry & Academic Cooperation in Chungnam National University (IAC); Jung, Sang-Hun; Woo, Sun-Hee; Kim, Sang- Kyum; Jeon, Eun-Seok; Lee, Yu-Jung; Meunikam, Manoj; Jalani, Hiteshkumar; Sharma, Niti; (205 pag.)KR2016/108281; (2016); A;,
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Related Products of 72080-83-2, A common heterocyclic compound, 72080-83-2, name is Benzyl (2-aminoethyl)carbamate, molecular formula is C10H14N2O2, 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.

1-((Dimethylamino)(dimethyliminio)methyl)-1H-[1,2,3]triazolo[4,5-b]pyridine 3-oxide hexafluorophosphate(V) (HATU, 1.87 g, 4.92 mmol) and triethylamine (3.43 mL, 24.6 mmol) were subsequently added to a solution of (S)-22-(tert-butoxycarbonyl)-10,19,24-trioxo-39-sulfo-3,6,12,15-tetraoxa-9,18,23-triazanonatriacontanoic acid (4.5 mmol) in dry dichloromethane (40 mL). Triethylamine (1.82 mL, 13.1 mmol) was added to a suspension of (2-amino-ethyl)-carbamic acid benzyl ester hydrochloride (5, 1.93 g, 8.37 mmol) in dry dichloromethane (20 mL) and the resulting mixture was added to the above solution. The mixture was stirred overnight at room temperature. After 16 hours, another portion of 1-((dimethylamino)(dimethyliminio)methyl)-1H-[1,2,3]triazolo[4,5-b]pyridine 3-oxide hexafluorophosphate(V) (HATU, 0.38 g, 1 mmol), triethylamine (2.00 mL, 14.3 mmol) and (2-amino-ethyl)-carbamic acid benzyl ester hydrochloride (5, 0.40 g, 1.70 mmol) were added and the mixture was stirred for another 2 hours. The solution was washed with 1 M aqueous hydrochloric acid (2¡Á100 mL) and brine (50 mL), dried over anhydrous sodium sulfate and evaporated to dryness. Crude (S)-29-(tert-butoxycarbonyl)-3,8,17,26,31-pentaoxo-1-phenyl-2,10,13,19,22-pentaoxa-4,7,16,25,30-pentaazahexatetracontane-46-sulfonic acid (6) was used for the next step without further purification. (0579) Yield: quantitative (based on ELSD). (0580) LC-MS purity: 83% (ELSD). (0581) LC-MS Rt (Kinetex C18, 4.6 mm¡Á50 mm, acetonitrile/water 20:80 to 100:0+0.1% FA): 3.35 min. (0582) LC-MS m/z: 989.1 (M+H)+.

The synthetic route of 72080-83-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Novo Nordisk A/S; Gao, Xiang; Zhang, Xujia; Guan, Hongtao; Thoegersen, Henning; Sass-Oerum, Kristian; Iversen, Lars Fogh; Noergaard, Per; Joergensen, Sebastian Beck; Hansen, Kristian Tage; Wang, Yi; Frieboes, Kilian Waldemar Conde; Wieczorek, Birgit; (259 pag.)US2018/339057; (2018); A1;,
Amide – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 6919-61-5, name is N-Methoxy-N-methylbenzamide, 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 6919-61-5, name: N-Methoxy-N-methylbenzamide

N-Methoxy-N-methyl benzamide 20 (0.1 g, 0.60 mmol) was dissolved in anhydrous diethyl ether (2.01 ml). The solution was cooled to 0 C. To this, vinyl magnesium bromide solution (0.91 ml, 1.0 M in THF) was added dropwise over 30 min at 0 C. After the completion of addition, the reaction mixture was stirred for a further 60 min at 0 C and for 30 min at room temperature. It was then quenched with 1M HCl at 0 C. The reaction mixture was diluted with diethyl ether. The organic layer was washed with brine, dried over Na2SO4,concentrated in vacuo, purified on silica gel (3:1 hexanes/EtOAc) to afford 0.04 g of 7 (55%) as a colorless oil. 1H NMR (400 MHz, CDCl3) ae 7.95 (d, J = 8.3 Hz, 2H), 7.60-7.55 (m, J = 7.4 Hz,1H), 7.49 (t, J = 8.0 Hz, 2H), 7.15 (dd, J = 10.5 Hz, 6.6 Hz, 1H), 6.40 (d, J = 17.1 Hz, 1H), 5.90(d, J = 10.6 Hz, 1H); 13C NMR (100 MHz, CDCl3) ae 191.2, 137.5, 133.1, 132.6, 130.2, 128.8,128.7. HRMS C9H9O [M+H]+ Expected: 133.0648, Found: 133.0646.

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, N-Methoxy-N-methylbenzamide, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Korwar, Sudha; Nguyen, Thuy; Ellis, Keith C.; Bioorganic and Medicinal Chemistry Letters; vol. 24; 1; (2014); p. 271 – 274;,
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Reference of 207405-68-3, The chemical industry reduces the impact on the environment during synthesis 207405-68-3, name is tert-Butyl endo-3-amino-8-azabicyclo[3.2.1]octane-8-carboxylate, I believe this compound will play a more active role in future production and life.

General procedure: To the solution of compound 13 (0.11 g, 0.25 mmol) and bicyclicamine (0.38 mmol) in THF (3 mL) was added DIPEA (0.38 mmol). Afterstirred at R.T. for 1 h, the reaction mixture was diluted with EtOAc,washed with brine, dried over MgSO4, and evaporated. The residue waspurified by column chromatography to give the product.4.1.6. tert-butyl (endo)-3-((2,6-dichloro-8-((2-fluoro-4-(methylsulfonyl)phenyl)amino)pyrimido[5,4-d]pyrimidin-4-yl)amino)-8-azabicyclo[3.2.1]octane-8-carboxylate (14a)Yellow solid, 32% yield. 1H NMR (300 MHz, CDCl3) delta (ppm): 9.12(d, J=3.2 Hz, 1H), 8.95 (t, J=8.1 Hz, 1H), 7.80 (m, 2H), 7.45 (d,J=7.7 Hz, 1H), 4.50-4.20 (m, 3H), 3.10 (s, 3H), 2.50-2.10 (m, 4H),2.00-1.80 (m, 4H), 1.50 (s, 9H). HRMS-ESI (m/z) calcd forC25H28Cl2FN7O4S [M+Na]+: 634.1182, found 634.1234

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 endo-3-amino-8-azabicyclo[3.2.1]octane-8-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Fang, Yuanying; Xu, Jun; Li, Zhifeng; Yang, Zunhua; Xiong, Lijuan; Jin, Yi; Wang, Qi; Xie, Saisai; Zhu, Wufu; Chang, Sheng; Bioorganic and Medicinal Chemistry; vol. 26; 14; (2018); p. 4080 – 4087;,
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