Month: August 2021

Application of 147356-78-3, The chemical industry reduces the impact on the environment during synthesis 147356-78-3, name is N-Methoxy-N-methylcyclopropanecarboxamide, I believe this compound will play a more active role in future production and life.

Intermediate 402-Cyclopropyl-1H-pyrrolo[2,3-b]pyridine To a stirred mixture of lambda/-boc-2-aminopicoline (10.4g) in dry THF (70ml) in an ice/ salt bath was added, under an atmosphere of nitrogen, n-butyl lithium (2M solution in cyclohexane, 50ml), keeping the temperature below 00C. The reaction was stirred below 00C for 1 h before the addition of a solution of lambda/-methyl-lambda/-(methyloxy)cyclopropanecarboxamide (7.5g) (available from Pfaltz-Bauer) in dry THF (20ml). The reaction mixture was stirred at 00C for 2h then warmed to 100C and poured into 5M hydrochloric acid (130ml). The mixture was heated at 600C for 2h, cooled and the aqueous layer separated. The aqueous layer was basified by the addition of 10M sodium hydroxide, with ice/water cooling, until the pH was 10 – 12. The resulting mixture was extracted with DCM (2x100ml) and the combined organic extracts were washed with water (50ml), dried using a hydrophobic frit and evaporated to give the title compound (7.89g). LC/MS R1 0.78min m/z 159 [MH+]. Method B

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

Reference:
Patent; GLAXO GROUP LIMITED; WO2009/147188; (2009); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 7326-73-0, name is 3-(N,N-Dimethylsulfamoyl)benzoic acid, 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 7326-73-0, name: 3-(N,N-Dimethylsulfamoyl)benzoic acid

To a solution of 3-(dimethylsulfamoyl)benzoic acid (75.72 mg, 330.31 pmol) in DCM (10 ml_) was added HATU (125.59 mg, 330.31 pmol) and DIPEA (155.24 mg, 1 .20 mmol). The solution was stirred for 10 min and then intermediate i-1 b (81 mg, 300.28 pmol) was added. The solution was stirred at 30 C for 12hr. The reaction solution was poured into water (50 ml_) and extracted with EtOAc (100 ml_). The organic layer was washed with brine (50 ml_), dried (Na2SC>4) and concentrated in vacuum. To the residue was added MeOH (20 ml_) and stirred for 20 min, a white solid was formed. The solid was filtered and dried in vacuum to give compound 13 as a white solid. LCMS (ESI) m/z: [M+H]+ = 444.9. 1 H NMR (400 MHz, DMSO-d6) d= 12.49 (s, 1 H), 9.32 (t, J=5.6 Hz, 1 H), 8.27-8.25 (m, 2H), 7.96-7.90 (m, 3H), 7.81 -7.80 (m, 1 H), 7.64 (s, 1 H), 7.46-7.42 (m, 2H), 7.33-7.30 (m, 1 H), 4.23 (d, J=5.6 Hz, 2H), 2.65 (s, 6H) ppm.

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, 3-(N,N-Dimethylsulfamoyl)benzoic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; FOGHORN THERAPEUTICS INC.; ANTHONY, Neville, John; MILLAN, David, Simon; VASWANI, Rishi, G.; SCHILLER, Shawn, E.R.; (239 pag.)WO2019/152437; (2019); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 154748-63-7, 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. 154748-63-7, name is tert-Butyl (3-hydroxycyclobutyl)carbamate, This compound has unique chemical properties. The synthetic route is as follows.

3-(tert-butoxycarbonylamino)cyclobutyl 4-methylbenzenesulfonate 3-(tert-butoxycarbonyl amino)cyclobutyl 4-methylbenzenesulfonate was prepared from tert-butyl 3-hydroxycyclobutylcarbamate and 4-methylbenzene-1-sulfonyl chloride using Method M. The product was purified by flash chromatography eluting with EtOAc in hexane (0% to 17% gradient) to yield tert-butyl N-(3-[[(4-methylbenzene)sulfonyl]oxy]cyclobutyl)carbamate as a yellow solid (915 mg, 53%).

The chemical industry reduces the impact on the environment during synthesis tert-Butyl (3-hydroxycyclobutyl)carbamate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Merck Patent GmbH; SHERER, Brian A.; KARRA, Srinivasa; XIAO, Yufang; (407 pag.)US2016/376283; (2016); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Related Products of 4093-31-6, 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. 4093-31-6, name is Methyl 4-acetamido-5-chloro-2-methoxybenzoate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A stirred suspension of methyl 4-(acetylamino)-5-chloro-2- (methyloxy)benzoate (103g, 0.4mol) in dry DCM (460ml) was cooled to 00C under argon. A solution of BCI3 in DCM (1 M) (800ml) was then cannulated directly from the reagent bottle with argon pressure by T-piece bleed control so that the rate of addition was easily controlled. The apparatus was set to control the internal temperature at 00C during the addition. The addition was carried out over 55 minutes. The temperature range (internally) varied 0?11C. During the addition the apparatus was kept under argon only by the supply of BCI3 through argon pressure. The vessel was capped with a silica drying tube. The suspension was present throughout the addition – it did not dissolve at any stage. After the complete addition of the BCI3 solution the temperature was adjusted to 15C and stirred for 1.5 hours under argon. After 1.5 hours under argon the mixture was poured into water (1 L), ice (35Og) with stirring and more DCM (0.8L) and water (0.8L) was added to this mixture. The whole mixture was transferred to a 5L separating funnel and vigorously shaken (solids virtually dissolved). Layers were separated and the aqueous layer extracted with DCM (2x 0.8L). The combined organic extracts were dried (MgSO4) and combined with the same extract obtained from repeating the above-mentioned reaction using the same reactant quantities. The combined extracts from the two experiments were concentrated in vacuo to a cream solid. This solid was stirred with Et2O (800ml) for 10 minutes. Then hexane (800ml) was added and the reaction continued to stir at room temperature for 0.5 hours. The solid was then filtered and washed with hexane (2 x 300ml) and dried at 45C under vacuum for 16 hours (185g, 0.759mol, 95%th) and identified as pure product. LCMS RT 2.44 mins (MH+)HPLC -99% (RT 11.9 min) at 254nm detection

The synthetic route of Methyl 4-acetamido-5-chloro-2-methoxybenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; WO2007/96352; (2007); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 2835-68-9, 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. 2835-68-9 name is 4-Aminobenzamide, 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.

To a solution of 4-aminobenzamide (5.0 g, 36.7 mmol) and pyridine (2.9 g, 36.7 mmol)) in dry CH2Cl2 (100 mL) at -10 C., phenyl chloroformate (6.9 g, 44.1 mmol) was added dropwise, stirred at -10 C. for 30 min and then at room temperature for 30 minutes The reaction mixture was diluted with CH2Cl2 (100 mL) and washed with water (2×70 mL). The organic layer was dried over anhydrous Na2SO4 and concentrated to get the crude product. The crude product was dissolved in diethyl ether (15 mL) and sonicated for 10 minutes and then pentane (30 mL) was added, the resulting solid was filtered and washed with pentane to give phenyl 4-carbamoylphenylcarbamate (7.2 g, 77% yield).

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

Reference:
Patent; WYETH LLC; VENKATESAN, Aranapakam Mudumbai; CHEN, Zecheng; DEHNHARDT, Christoph Martin; DOS SANTOS, Osvaldo; DELOS SANTOS, Efren Guillermo; ZASK, Arie; VERHEIJEN, Jeroen Cunera; KAPLAN, Joshua Aaron; RICHARD, David James; AYRAL-KALOUSTIAN, Semiramis; MANSOUR, Tarek Suhayl; GOPALSAMY, Ariamala; CURRAN, Kevin Joseph; SHI, Mengxiao; (113 pag.)US2017/119778; (2017); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

These common heterocyclic compound, 24243-71-8, name is Propane-1-sulfonamide, 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. HPLC of Formula: C3H9NO2S

A mixture of 5-(6-chloro-2-phenylpyrimidin-4-yl)-1,3-dimethylpyridin-2(1H)-one (51 mg, 0.2 mmol), propane-1-sulfonamide (37 mg, 0.3mmo1), Pd(dba)3 (18 mg, 0.02 mmol), Xphos (9 mg, 0.2 mmol), CsCO3 (130 mg, 0.4 mmol) in dioxane (3 mL) was stirred and heated at 90 C. for 16 hr. The reaction mixture was diluted with water and extracted with EtOAc (3*). The extracts were combined, washed with brine, dried (Na2SO4) and concentrated. The residue was purified by flash column chromatography (EA:Hex, 0-100%) to provide the 16 mg (23%) of the desired product as an off-white solid. 1H NMR (400 MHz, DMSO-d6) delta ppm 0.99 (t, J=7.45 Hz, 3H) 1.78 (sxt, J=7.38 Hz, 2H) 2.14 (s, 3H) 3.32 (s, 3H) 3.62 (s, 3H) 3.63-3.69 (m, 2H) 7.06 (s, 1H) 7.51-7.59 (m, 3H) 7.99 (s, 1H) 8.41-8.52 (m, 2H) 8.64 (d, J=2.27 Hz, 1H) 11.26 (br. s., 1H).

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

Reference:
Patent; CELGENE QUANTICEL RESEARCH, INC.; Bennett, Michael John; Betancort, Juan Manuel; Boloor, Amogh; Kanouni, Toufike; Stafford, Jeffrey Alan; Veal, James Marvin; Wallace, Michael Brennan; (250 pag.)US2017/298040; (2017); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 107017-73-2,Some common heterocyclic compound, 107017-73-2, name is tert-Butyl (1-(hydroxymethyl)cyclopropyl)carbamate, molecular formula is C9H17NO3, 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.

tert-Butyl (1-(hydroxymethyl)cyclopropyl)carbamate 6a (92 mg, 0.49 mmol) was placed in a reaction flask, followed by addition of 4-(3-(6-hydroxypyridin-3-yl)-4,4-dimethyl-5-oxo-2-thioxoimidazolidin-1-yl)-2-(trifluoromethyl)benzonitrile 10c (100 mg, 0.24 mmol), triphenylphosphine (97 mg, 0.37 mmol), 5 mL of dichloromethane, and diisopropyl azodicarboxylate (75 mg, 0.37 mmol), successively. The reaction solution was stirred for 2 hours. The reaction solution was purified by thin layer chromatography with elution system A, and subsequently with elution system B to obtain the title compound tert-butyl (1-(((5-(3-(4-cyano-3-(trifluoromethyl)phenyl)-5,5-dimethyl-4-oxo-2-thioxoimidazolidin-1-yl)pyridin-2-yl)oxy)methyl)cyclopropyl)carbamate 11a (40 mg, yield 28.4%) as a white solid. MS m/z (ESI): 576.2 [M+1]

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 (1-(hydroxymethyl)cyclopropyl)carbamate, its application will become more common.

Reference:
Patent; Shanghai Hengrui Pharmaceutical Co., Ltd.; Jiangsu Hengrui Medicine Co., Ltd.; Lu, Hejun; Sun, Piaoyang; Fei, Hongbo; Jiang, Hongjian; Wang, Haowei; Dong, Qing; US2015/225381; (2015); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 6971-74-0, The chemical industry reduces the impact on the environment during synthesis 6971-74-0, name is N-Tosylbenzamide, I believe this compound will play a more active role in future production and life.

General procedure: N-Benzoylsulfonamide 1a (27.5 mg, 0.1 mmol), [RhCl2Cp*]2 (1.2 mg, 0.002 mmol), and Cu(OAc)2·H2O (40.0 mg, 0.20 mmol) were loaded in a dry vial, which was subjected to evacuation/flushing with dry argon three times. Anhydrous toluene (1.0 mL) solution of tert-butyl acrylate 2a (17.4 muL, 0.12 mmol) was syringed into the mixture, which was then stirred at 130 C for 24 h or until the starting material had been consumed as determined by TLC. Upon cooling to room temperature, all volatiles were evaporated and the residue was purified by preparative TLC (ethyl acetate/hexane 1:2) to give isoindolinone 3a in 88% yield

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

Reference:
Article; Zhu, Chen; Falck, John R.; Tetrahedron; vol. 68; 45; (2012); p. 9192 – 9199;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Related Products of 5238-56-2, 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. 5238-56-2 name is N-(2-Hydroxyethyl)methacrylamide, 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.

General procedure: To a solution of glycosyl donor10 1 (0.635 gm, 1 mmol), glycosyl acceptor 10b (0.142 g 1.1 mmol) and 4 A molecular sieves powder (100 mg) in anhydrous CH2Cl2 (10 mL) was added AuBr3 (0.031 g, 0.07 mmol) under argon atmosphere at room temperature. The reaction mixture was stirred at room temperature for the specified time and the completion of the reaction is judged by TLC analysis. The reaction mixture was filtered through Celite and the filtrate was concentrated in vacuo to obtain a crude residue which was purified by conventional silica gel column chromatography using ethyl acetate-petroleum ether as mobile phase to obtain compound 11b.

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

Reference:
Article; Thadke, Shivaji A.; Kar, Mritunjoy; Gupta, Sayam Sen; Hotha, Srinivas; Carbohydrate Research; vol. 346; 12; (2011); p. 1511 – 1518;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

758-96-3, name is N,N-Dimethylpropionamide, belongs to amides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Application In Synthesis of N,N-Dimethylpropionamide

Scheme AStep a1a: compound A2 (N,N-2-trimethyl-3-oxopentanamide)32.1 ml (0.35 mol) phosphoryl trichloride (POCI3) were dissolved in 100 mL of toluene. 32.6 ml (0.3 mol) A , V-dimethylpropionamide (A1) (dissolved in 50 mL toluene) were added to the resulting solution under stirring under an inert gas atmosphere. The reaction mixture was heated to 80C for 6 h, allowed to cool to RT and stirred for another 12 h at RT. After evaporation of toluene under reduced pressure, the resulting mixture was stirred for 2 h. 100 mL toluene were then added, the resulting mixture was cooled to below 0C and icy water (100 mL) was added. Then, 24 g of solid NaOH, dissolved in water, were added to the mixture. After 1 h of stirring, 47.7 g Na2C03 as solid were added and the resulting mixture was stirred for 16 h at RT. The organic layer was separated, dried over MgS04 and distilled (0.8 bar, 78-82C). 10.8 g (46%) of A2 was obtained in form of a colorless solid.

The synthetic route of 758-96-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GRUeNENTHAL GMBH; BUSCHMANN, Helmut, Heinrich; HOLENZ, Joerg; WO2011/157390; (2011); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics