Month: November 2020

49805-30-3, 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. 49805-30-3, name is 2-Azabicyclo[2.2.1]hept-5-en-3-one belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

1.7. Preparation of (+-)-1-amino-4-(hydroxymethyl)-2-cyclopentene in the presence of additives such as water or various alcohols A 10 ml round-bottom flask was charged with 0.50 g (4.66 mmol) of (+-)-2-azabicyclo[2.2.1]hept-5-en-3-one and 0.30 g (13.7 mmol) of lithium borohydride in 7.5 ml of abs. dioxane, and the mixture was heated to 60 C. At this temperature, over the course of 30 min, X mmol of alcohol Y was added dropwise using a syringe. The mixture is then stirred for 2 h at 60 C., cooled to about 20 C. and poured into about 10 ml of semi-concentrated HCl. The content was then determined directly using a quantitative ion-chromatographic method (cf.

The synthetic route of 2-Azabicyclo[2.2.1]hept-5-en-3-one has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Lonza AG; US2002/10360; (2002); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

3984-14-3,Some common heterocyclic compound, 3984-14-3, name is N,N-Dimethylsulfamide, molecular formula is C2H8N2O2S, 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.

Example 6; N’-(3-chloro-5-oxo-5H-pyridor4′,3′:4,51cycloheptarL2-^lpyridine-7-yl)-N,N-dimethylsulfamide (Compound 7); To a stirred solution of 3,7-dichloro-5H-pyrido[4′ ,3′ :4,5]cyclohepta[l,2-&]pyridin-5-one(80 mg, 0.29 mmol) in dioxane (5 mL) were added Pd2(dba)3 (13 mg, 0.014 mmol), 9,9-dimethyl-4,5- bis(diphenylphosphino)xanthene (25 mg, 0.043 mmol), N,N-dimethylsulfamide (36 mg, 0.29 mmol), and Cs2CO3 (0.28 g, 0.87 mmol). The reaction mixture was heated to 95 0C for 2 h, cooled to room temperature, treated with water, and extracted with EtOAc. The combined organics were washed with brine, dried (Na2SO4), concentrated, and purified by flash chromatography to afford the title compound. 1H NMR (600 MHz, CDCl3) delta 8.79 (d, IH); 8.86 (d, 1H);8.76 (s, IH); 8.66 (br s, IH); 8.54 (d, IH); 7.96 (s, IH); 7.38 (d, IH); 7.27 (d, IH); 2.99 (s, 6H). LRMS (ESI) calc’d for (C15H13ClN4O3S) [M+H]+, 365.0; found 365.1.

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

Reference:
Patent; MERCK & CO., INC.; WO2007/50401; (2007); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

The chemical industry reduces the impact on the environment during synthesis 3144-09-0, name is Methylsulfonamide, I believe this compound will play a more active role in future production and life. 3144-09-0

To a 50 mL three-necked flask, add 1.22 g (10.0 mmole) of benzoic acid and 12 mL of chloroform and stir at room temperature for about 5 minutes. Thereafter, the internal temperature was adjusted to around 5 C. by cooling with external cooling in an ice water bath, and then 1.484 g (5.0 mmole) of triphosgene and 3.036 g (30 mmole) of triethylamine were added in turn, (10.0 mmole) of methanesulfonamide was added thereto, and the mixture was stirred for about 5 minutes. Then, the ice water bath was removed and the temperature was raised to room temperature. While stirring for about 1 hour, the reaction was carried out by thin film chromatography (TLC) After confirming the completion of the reaction, the reaction solvent was distilled off under reduced pressure, and 15 mL of water was added to the resulting solid to dissolve the solid salt formed by the neutralization reaction of triethylamine and hydrochloric acid produced as a by-product The desired compound, acylsulfonamide, is dispersed in a solid form and stirred. After filtration, the filtrate was washed with water, and the obtained solid was dried to obtain 1.89 g (yield: 94.9%) of acyl sulfoneamide as a target compound in a solid form.

The chemical industry reduces the impact on the environment during synthesis 3144-09-0. I believe this compound will play a more active role in future production and life.

Reference:
Patent; HANKYONG NATIONAL UNIV. Industry-University Cooperation Foundation; Kim Mi-su; Han Gi-jong; (8 pag.)KR2017/136043; (2017); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

78888-18-3, The chemical industry reduces the impact on the environment during synthesis 78888-18-3, name is tert-Butyl allylcarbamate, I believe this compound will play a more active role in future production and life.

A degassed suspension of Example 294E (2.50 g, 4.51 mmol), Example 314A (2.62 g, 5.87 mmol), and potassium fluoride (0.340 g, 5.87 mmol) in toluene (45 mL) was treated with Pd(PPh3)4 (0.360 g, 0.316 mmol), degassed twice more, and then heated to 115 C. for 14 hours. The suspension was cooled to room temperature and the solvent was removed under reduced pressure. The resulting solid was triturated with ethanol/dichloromethane (10:1) (100 mL) and collected by vacuum filtration provide the desired product (2.3 g, 90%). LCMS (Thermoquest AQA single-quad MS, Genesis C18 column, 3 ?m particle size, 33?4.6 mm; 70% 50 mM ammonium acetate in water to 95% acetonitrile over 6 min, 0.8 to 0.5 mL/min); MS m/e 584.6 (M+H)+, Rt=4.1 minutes; 1H NMR (DMSO-d6, 400 MHz) ? 9.51 (s,1H), 7.99 (d, J=8.0 Hz,1H), 7.95 (s, 1H), 7.70 (d, J=8.0 Hz, 1H), 7.63 (s, 1H), 7.58 (d, J=8.4 Hz, 1H), 7.35 (s, 1H), 7.32 (d, J=8.4 Hz, 1H), 7.21 (d, J=1.5 Hz, 1H), 7.15 (dd, J=7.8 Hz, 7.0 Hz, 1H), 7.08 (dd, J=8.0 Hz, 1.9 Hz, 1H), 6.58 (d, J=16.2 Hz, 1H), 6.21 (td, J=16.2 Hz, J=5.5 Hz, 1H), 5.65 (br s, 1H), 4.04 (s, 3H), 3.91 (s, 3H), 3.80 (br m, 2H), 1.42 (s, 9H).

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

Reference:
Patent; Betschmann, Patrick; Burchat, Andrew; Calderwood, David; Curtin, Michael L.; Davidsen, Steven K.; Davis, Heather M.; Frey, Robin R.; Heyman, Howard R.; Hirst, Gavin; Hrnciar, Peter; Michaelides, Michael; Rafferty, Paul; US2005/20619; (2005); 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. 67442-07-3 name is 2-Chloro-N-methoxy-N-methylacetamide, 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. 67442-07-3

4-Iodo-1-(4-methoxybenzyl)-1H-pyrazole (8.1 g, 26 mmol) was dissolved in THF (50 mL) and cooled in an ice bath. Isopropylmagnesium chloride (2.9 M, 8.9 mL, 26 mmol) was added slowly. The reaction mixture was stirred for 10 minutes, and then 2- chloro-N-methoxy-N-methylacetamide (3.5 g, 26 mmol) dissolved in THF (15 mL) was added slowly by syringe. The reaction mixture was warmed to ambient temperature and stirred for 1 hour. The reaction mixture was partitioned between EtOAc and iN HC1, and the organic layer was dried over sodium sulfate, filtered and concentrated to afford crude 2-chloro-1-(l-(4- methoxybenzyl)- 1 H-pyrazol-4-yl)ethanone (7.1 g, 27 mmol, 104 percent yield) as an amber oil that slowly solidified.

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

Reference:
Patent; ARRAY BIOPHARMA INC.; CELGENE CORPORATION; ALLEN, Shelley; BOYS, Mark Laurence; CHICARELLI, Mark J.; FELL, Jay Bradford; FISCHER, John P.; GAUDINO, John; HICKEN, Erik James; HINKLIN, Ronald Jay; KRASER, Christopher F.; LAIRD, Ellen; ROBINSON, John E.; TANG, Tony P.; BURGESS, Laurence E.; RIEGER, Robert Andrew; PHENEGER, Jed; SATOH, Yoshitaka; LEFTHERIS, Katerina; RAHEJA, Raj K.; BENNETT, Brydon L.; (223 pag.)WO2016/90285; (2016); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

116091-63-5, Adding a certain compound to certain chemical reactions, such as: 116091-63-5, name is 2-Methoxy-5-(2-oxopropyl)benzenesulfonamide, 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 116091-63-5.

a) 2-Methoxy-5-(2-oxopropyl)-benzene sulfonamide (37.3 gm, 153.3 mmol), 2-(2-ethoxyphenoxy)-1-ethanamine (29.8 gm, 164.4 mmol) and methanol (250 mL) were taken into a one liter stainless steel flask and mixed well. Catalyst Raney nickel (8 gm) was added to the flask and the mixture hydrogenated at 50 C. at hydrogen pressure of 40 psi for 30 hrs. The catalyst was removed by filtration and solvent from the filtrate was distilled off completely at 50 C. under vacuum. The dark brown crude obtained was treated with methanolic hydrochloric acid (175 mL) at 0-5 C. under stirring. Tamsulosin hydrochloride formed as a solid was filtered, washed with ethyl acetate (200 mL), suspended in methanol (120 mL) and the methanol slurry filtered to obtain off white solid material. It was dried for 3 hrs at 80 C. to give racemic tamsulosin hydrochloride. Melting point 255-257 C., chemical purity of 98.8 area % (by HPLC) and R,S ratio of 51.45:48.55 (by chiral HPLC).

According to the analysis of related databases, 116091-63-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; DIVI’S LABORATORIES LIMITED; US2006/79714; (2006); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

627-12-3, Adding a certain compound to certain chemical reactions, such as: 627-12-3, name is Propyl 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 627-12-3.

General procedure: CuI (10mol%) and EDA (10mol%) were added to a mixtureof O-alkyl carbamate (1mmol), NaOtBu (1.5mmol) and aryl halide (1mmol) in 2mL toluene and the mixture wasstirred for the appropriate time, which was determined byTLC monitoring, at 100C. After completion of the reaction,the catalyst was removed by filtration and 20mL H2Owas added to the filtrate. The resultant mixture was extractedwith CHCl3.Then the organic phase was washed with water(2 ¡Á 10mL) and dried over anhydrous Na2SO4.After evaporationof CHCl3under reduced pressure, the correspondingcrude product was purified by flash chromatography to givethe desired pure cross-coupling product in good to excellentyield. In the case of using arylboronic acids as couplingpartners, Cu(OAc)2 was employed instead of CuI.

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, Propyl carbamate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Sardarian, Ali Reza; DindarlooInaloo, Iman; Zangiabadi, Milad; Catalysis Letters; vol. 148; 2; (2018); p. 642 – 652;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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 631-58-3 as follows. 631-58-3

Into a solution of Compound 94 (145 mg, 0.33 mmol) in THF (10 mL) at 00 C was added phenyltrimethylammonium tribromide (125 mg, 0.33 mmol). The mixture was stirred at O 0 C for 1 hour, quenched by ice addition, extracted with methylene chloride. The combined extracted was dried (Na2SO4), filtered and concentrated to give crude 75a (200mg).Into a solution of 75a (52 mg, 0.1 mmol) in 3 mL of EtOH was added ethanethioamide (0.2 mmol) at room temperature. The resulting solution was stirred at room temperature for 4 hours. The solvent was removed under reduced pressure and the residue was taken up with ethyl acetate. The solution was treated with saturated solution of NaHCO3 and extracted with ethyl acetate. The combined extracts were dried (NaaSClambdai) and concentrated. Column chromatography on silica gel (eluted with 10-70% ethyl acetate in hexanes) gave Compound 95 (40 mg).1H NMR (300 MHz, CDCI3) 510.40 (brs, 1 H), 7.54-7.42 (m, 5H), 7.02 (t, J = 8.5Hz, 2H), 2.65 (s, 3H), 1.90 (s, 3H).MS (ESI) [M+H+]: 496.

According to the analysis of related databases, 631-58-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SYNTA PHARMACEUTICALS CORP.; WO2007/87427; (2007); A2;,
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. 630-22-8, name is 2,2-Dimethylpropanethioamide, A new synthetic method of this compound is introduced below., 630-22-8

at room temperature, to dimethylacetamide (35mL) in a (3- (2- (t-butyl) -5- (2-chloro-pyrimidin-4-yl) thiazol-4-yl) -2-fluorophenyl ) allyl carbamate (3.21g, 9.18mmol, 1.0eq.) was added N- succinimide (1.64g, 9.21mmol, 1.0eq.).When LCMS showed complete disappearance of the starting material, 2,2,2-trimethoxy thio acetamide (1.3g, 11.1mmol, 1.2eq.) And the reaction was heated overnight at 60 deg.] C.LCMS showed the reaction was complete.The reaction was poured into water (250mL), and extracted with ethyl acetate content.Extract was dried over sodium sulfate, filtered, and concentrated under reduced pressure.With 20% ethyl acetate / heptane, silica gel chromatography (300g, 3 “diameter column) to give the crude product, in the form of an oil to provide (3- (2- (t-butyl) -5- (2- chloro-pyrimidin-4-yl) thiazol-4-yl) – 2-fluorophenyl) allyl carbamate (2.92g, 70% yield)

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; Pulaixike Company; Zhang, Chao; Ibrahim, Prabha N; Nespi, Marika; Shi, Songyuan; Spevak, Wayne; Habets, Gaston G; Burton, Elizabeth A; Hirth, Klaus-Peter; (181 pag.)CN105228983; (2016); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

627-12-3, These common heterocyclic compound, 627-12-3, name is Propyl 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.

General procedure: CuI (10mol%) and EDA (10mol%) were added to a mixtureof O-alkyl carbamate (1mmol), NaOtBu (1.5mmol) and aryl halide (1mmol) in 2mL toluene and the mixture wasstirred for the appropriate time, which was determined byTLC monitoring, at 100C. After completion of the reaction,the catalyst was removed by filtration and 20mL H2Owas added to the filtrate. The resultant mixture was extractedwith CHCl3.Then the organic phase was washed with water(2 ¡Á 10mL) and dried over anhydrous Na2SO4.After evaporationof CHCl3under reduced pressure, the correspondingcrude product was purified by flash chromatography to givethe desired pure cross-coupling product in good to excellentyield. In the case of using arylboronic acids as couplingpartners, Cu(OAc)2 was employed instead of CuI.

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 627-12-3.

Reference:
Article; Sardarian, Ali Reza; DindarlooInaloo, Iman; Zangiabadi, Milad; Catalysis Letters; vol. 148; 2; (2018); p. 642 – 652;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics