Amides-buliding-blocks

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. 116861-31-5, name is tert-Butyl (3-chloropropyl)carbamate, A new synthetic method of this compound is introduced below., COA of Formula: C8H16ClNO2

To a refluxing solution of hydrazine hydrate (6.40 g, 128.00 mmol) in ethanol (14.5 mL) was added a solution of tert-butyl 3-chloropropylcarbamate (9A) (3.80 g, 19.62 mmol) in ethanol (14.5 mL), dropwise over 80 min. The mixture stirred at reflux for 1 h. The reaction mixture was then evaporated and the residue diluted with diethyl ether (60 mL). The two layers were separated. The organic layer was washed with saturated sodium carbonate solution (17 mL) and evaporated to give tert-butyl 3-hydrazinylpropylcarbamate (10A) (1.60 g, 8.45 mmol, 43%) as a yellow oil. The crude material was used in the next step without further purification. ESMS m/z 190 (M+H)+.

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; SOVA PHARMACEUTICALS, INC.; STEIN, Gregory; RAO, Srinivas, G.; DURON, Sergio, G.; CHAPMAN, Justin; SYDSERFF, Simon, G.; WO2014/18571; (2014); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Some common heterocyclic compound, 54468-86-9, name is 2-Amino-N,N-dimethylbenzenesulfonamide, molecular formula is C8H12N2O2S, 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. Formula: C8H12N2O2S

General procedure: To a solution of 2-(isopropylsulfonyl)aniline (3.0 g,15.1 mmol) in DMF (80 mL) was added sodium hydride (1.2 g,30.1 mmol, 60% in mineral oil) at 0 C. After stirring for 30 min,2,4,5-trichloropyrimidine was added to the reaction mixture followedby warming the mixture to room temperature. After stirringfor 2 h, the reaction mixture was quenched with ice and dilutedwith excess water. The precipitate was filtered and the solid wasdried by blowing nitrogen gas to obtain 3c as an off-white solid(3.75 g, 72%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 54468-86-9, its application will become more common.

Reference:
Article; Jang, Jaebong; Son, Jung Beom; To, Ciric; Bahcall, Magda; Kim, So Young; Kang, Seock Yong; Mushajiang, Mierzhati; Lee, Younho; Jaenne, Pasi A.; Choi, Hwan Geun; Gray, Nathanael S.; European Journal of Medicinal Chemistry; vol. 136; (2017); p. 497 – 510;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 67442-07-3, These common heterocyclic compound, 67442-07-3, name is 2-Chloro-N-methoxy-N-methylacetamide, 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.

C. Synthesis of Intermediate 22 [0244] A 3-neck flask was charged with 21 (100 g) and THF (800 mL). The solution was degassed three times by slowly applying vacuum, followed by breaking vacuum with nitrogen. The solution was cooled to -10 C. internal temperature. A solution of 2N i-PrMgCl solution in THF (125 g, 1.04 mole equiv) was added slowly while maintaining internal temperature at -10 C. to 0 C. The resulting mixture was then stirred for 30 minutes at -10 C. until reaction was complete. 2-Chloro-N-methoxy-N-methylacetamide (40.6 g, 1.20 mole equiv) was dissolved in MTBE (122 g, 1.22 wt equiv) and filtered through a 1 mum filter. The MTBE solution of the acetamide was then added slowly to the flask maintaining internal temperature at -10 C. to 0 C. Upon completion of the addition, the internal temperature was adjusted to 0 C. and agitated for 2 hours. After the reaction is complete, 1N HCl (750 g) was added slowly so that the internal temperature did not exceed 20 C. If necessary, the internal temperature was adjusted to 20 C. The layers were separated and the aqueous layer was extracted with MTBE (410 g). The organic layers were combined and dried over MgSO4. The MgSO4 was filtered off and rinsed with THF (200 g). The filtrate and rinse were concentrated under vacuum 10 volumes (1000 mL). Isopropanol (785 g) was added and small amounts of crystals began to form. This slurry was again concentrated under vacuum to 10 volumes (1000 mL). Isopropanol (785 g) was once again added and the slurry was concentrated under vacuum to 10 volumes (1000 mL). The internal temperature was adjusted to 20-25 C. and agitated for ca. 30 minutes. The slurry was filtered and rinsed with isopropanol (100 g) then dried under vacuum to provide 62.28 g (70.8%, 98% purity by HPLC) of the product 22 as an off-white to pale yellow solid. 1H NMR (400 MHz, CDCl3, delta): 8.19 (s, 1H), 8.12 (d, J=7.8 Hz, 1H), 7.82 (s, 1H), 7.67 (d, J=8.0 Hz, 2H), 7.52 (d, J=7.8 Hz, 1H), 4.71 (s, 2H). 19F NMR (376 MHz, CDCl3) delta -111.4 (s, 2F).

Statistics shows that 2-Chloro-N-methoxy-N-methylacetamide is playing an increasingly important role. we look forward to future research findings about 67442-07-3.

Reference:
Patent; Scott, Robert William; Wang, Fang; Shi, Bing; Mogalian, Erik; US2013/324496; (2013); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 94838-59-2, A common heterocyclic compound, 94838-59-2, name is tert-Butyl 4-aminophenethylcarbamate, molecular formula is C13H20N2O2, 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 2-(pyrrolidin-l-yl)acetic acid(l94 mg, 1.5 mmol), HATU (627 mg, l .65mmol) and DIPEA (582 mg, 4.5 mmol) in DCM (10 mL) was stirred at room temperature for 0.5 h. Then tert- butyl 4-aminophenethylcarbamate (354 mg, 1.5 mmol) was added and the reaction 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 (220 mg, 42.3 % yield). NMR (500 MHz, DMSO-riri) d: 9.74 (s, 1H), 7.53 (d, J= 8.3 Hz, 2H), 7.12 (d, J= 8.3 Hz, 2H), 6.86 (t, J= 5.3 Hz, 1H), 3.37 (s, 2H), 3.10 (dd, J= 13.9, 6.5 Hz, 2H), 2.70 (d, J= 3.3 Hz, 4H), 2.66 – 2.60 (m, 2H), 1.78 (dd, J= 6.1, 3.0 Hz, 4H), 1.37 (s, 9H).

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; ZHEJIANG VIMGREEN PHARMACEUTICALS, LTD; SUN, Sanxing; ZHAO, Long; HU, Chongbo; CHEN, Zhengshu; YE, Jinqi; (0 pag.)WO2020/2969; (2020); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 13304-62-6, name is N-Benzylacrylamide, 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 13304-62-6, Formula: C10H11NO

General procedure: To a solution of compound 5 (6) (3 mmol) and substituted acrylamide (3.3 mmol) in dry DMF was added Pd(OAc)2 (3%) and triethylamine (6 mmol). The reaction mixture was stirred under 100 C via microwave (500 w) for 7 min. Then the mixture was poured into 10% HCl ice water (200 ml) slowly with stirring. The suspension was filtered through a filter and filter cake was collected and dried. The crude product was purified by chromatography over silica gel to give compounds 7 or 8.

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-Benzylacrylamide, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Zhang, Yikai; Zhong, Hanyu; Lv, Zhiliang; Zhang, Mingfeng; Zhang, Tao; Li, Qisheng; Li, Ke; European Journal of Medicinal Chemistry; vol. 62; (2013); p. 158 – 167;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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. 25408-61-1, name is 2,2-Dimethoxy-N,N-dimethylacetamide, A new synthetic method of this compound is introduced below., Formula: C6H13NO3

A total of 5.0 g of 1H-indazole as a starting material was subjected to bromination and tert-butoxycarbonylation by the procedures of Production Examples I-26-a and I-26-b, was acetylated at the 3-position by the procedure of Production Example I-29-a, to give 2.5 g of tert-butyl 3-acetyl-1H-1-indazolecarboxylate. A total of 1.5 g of this product was treated with 5 N hydrochloric acid by the procedure of Production Example I-25-b and thereby yielded 860 mg of 1-(1H-3-indazolyl)ethanone. A solution of 240 mg of this product and 0.4 ml of N,N-dimethylformamide dimethylacetal in 5 ml toluene was heated under reflux for 9 hours. The solvent was evaporated, and the residue was purified and separated by silica gel column chromatography (ethyl acetate:hexane = 2:1), to give 88 mg of the title compound as a colorless powder.1H-NMR(400MHz, DMSO-d6) d 2.88 (3H, bs), 3.13 (3H, bs), 6.08 (1H, d, J = 13.1 Hz), 7.19 (1H, t, J = 7.6 Hz), 7.36 (1H, t, J = 7.6 Hz), 7.56 (1H, d, J = 7.6 Hz), 7.72 (1H, d, J = 13.1 Hz), 8.26 (1H, d, J = 7.6 Hz), 13.37 (1H, s)

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; Eisai Co., Ltd.; EP1380576; (2004); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 148017-28-1,Some common heterocyclic compound, 148017-28-1, name is tert-Butyl sulfamoylcarbamate, molecular formula is C5H12N2O4S, 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 mixture of 1-pentanol (0.43 g, 4.88 mmol, 1.0 equiv), N-tert- butoxycarbonyl-sulfamide {prepared from chlorosulfonyl isocyanate according to Y. Nishino et al., Organic Process Research & Development 2003, 7, 649-654} (1.02 g, 5.18 mmol, 1.06 equiv), triphenylphosphine (1.76 g, 6.71 mmol, 1.37 equiv) and ethyl acetate (5 mL) was added 1,1′-(azodicarbonyl)dipiperidine (ADDP) (1.55 g, 6.14 mmol, 1.26 equiv). The reaction mixture was stirred at room temperature for 14 h. After the solvents were removed in vacuo, the residue was purified by chromatography on silica gel (10% to 20% ethyl acetate in hexanes) to afford N- aminosulfonyl-ferf-butyl pentylcarbamate (0.849 g, 65%). LC-MS (3 min) iR = 1.74 min m/z 251 [M-CH3J+, 210 [M-C4H8]+; 1H NMR (400 MHz, CDCI3) delta 5.29 (br s, 2H), 3.68-3.64 (m, 2H), 1.69-1.61 (m, 2H), 1.53 (s, 9H), 1.37-1.24 (m, 4H)1 0.90 (t, J = 7.0 Hz, 3H); 13C NMR (100 MHz, CDCI3) delta 152.5, 84.1 , 47.6, 29.0, 28.4, 27.9, 22.1, 14.0.

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 sulfamoylcarbamate, its application will become more common.

Reference:
Patent; VITAE PHARMACEUTICALS, INC.; WO2006/83924; (2006); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 224309-64-2, These common heterocyclic compound, 224309-64-2, name is tert-Butyl (4-hydroxycyclohexyl)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.

To a stirred solution of tert-butyl (4-hydroxycyclohexyl)carbamate (25.0 g, 116.1 mmol, 1eq) in dry dicloromethane (250 ml_) was added triethylamine (32.2 ml_, 232.3 mmol) at 0 C under N2 atmosphere at room temperature. Mesyl chloride (10 ml_, 127.7 mmol) was added drop wise to the above reaction mixture after 15 min. Then reaction mixture was stirred at room temperature for 16 hour. The reaction mixture was quenched with aq. sodium bicarbonate, extracted with dichloromethane. The combined extracts were washed with water, brine and dried over anhydrous sodium sulphate, filtered and solvents evaporated from the filtrate under reduced pressure to obtain crude product which was purified by column chromatography to yield 25.0 g (73.5 %) of 4-((tert- butoxycarbonyl)amino)cyclohexyl methanesulfonate (INT-2). The final product was characterized by NMR.

Statistics shows that tert-Butyl (4-hydroxycyclohexyl)carbamate is playing an increasingly important role. we look forward to future research findings about 224309-64-2.

Reference:
Patent; PRIMETIME LIFE SCIENCES, LLC; JANAK, Khimchand Padia; (274 pag.)WO2019/50850; (2019); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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. 84713-20-2, name is Benzyl vinylcarbamate, A new synthetic method of this compound is introduced below., Safety of Benzyl vinylcarbamate

General procedure: Unless otherwise noted, the General Experimental Procedure was described as follows: To a solution of enecarbamate/enamide 1 (0.2 mmol) in alcohol (2.0 mL) was added the BNDHP (1.4 mg, 0.002 mmol), and the reaction mixture was stirred at 25 oC. When the starting materials disappeared with the inspection by TLC, the solvent was removed under reduced pressure. The residue was purified by flash column chromatography on silica gel eluting with petroleum ether/EtOAc to afford the product 2. S3

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; Chang-Fei, Zhang; Wei, Zou; Xiao-Yan, Ma; Xinjun, Hu; Yanli, Li; Tetrahedron; vol. 76; 16; (2020);,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 188345-71-3, 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. 188345-71-3 name is 2-Boc-2-Azabicyclo[2.2.1]hept-5-ene, 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.

In a method analogous to J. Malpass and C. Cox, Tetrahedron Lett., 1999, 40, 1419-1422, tert-butyl 2-azabicyclo[2.2.1]hept-5-ene-2-carboxylate is treated with diborane to afford a mixture of alcohols which is separated by chromatography. The desired alcohol tert-butyl 6-hydroxy-2-azabicyclo[2.2.1]heptane-2-carboxylate is then oxidized using the Swern procedure to afford the title compound.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Boc-2-Azabicyclo[2.2.1]hept-5-ene, and friends who are interested can also refer to it.

Reference:
Patent; Lampe, John W.; Watson, Paul S.; Slade, David J.; US2011/144150; (2011); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics