Month: March 2021

Adding a certain compound to certain chemical reactions, such as: 1444-94-6, name is 1,2-Cyclohexanedicarboximide, 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 1444-94-6, Application In Synthesis of 1,2-Cyclohexanedicarboximide

General procedure: To a suspension of corresponding cyclic imide 1a-1k (4mmol), potassium carbonate (4.4mmol) in DMF (5mL), 1-bromo-4-chlorobutane (1,2-dibromoethane (5 eq) for 2l, 1-bromo-3-chloropropane for 2m, 1-bromo-5-chloropentane for 2n) (4.4mmol) was added dropwise at 0C. The mixture was stirred at room temperature overnight and then partitioned between ethyl acetate (EA, 20mL) and water (30mL). The organic layer was washed successively with water (3¡Á30mL), saturated brine, and dried over anhydrous Na2SO4. The solvent was evaporated under vacuum and the residue was purified by column chromatography using petroleum ether(PE): EA (8:1) as eluent to give 2a-2n.

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, 1,2-Cyclohexanedicarboximide, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Xu, Mingshuo; Wang, Yu; Yang, Feipu; Wu, Chunhui; Wang, Zhen; Ye, Bin; Jiang, Xiangrui; Zhao, Qingjie; Li, Jianfeng; Liu, Yongjian; Zhang, Junchi; Tian, Guanghui; He, Yang; Shen, Jingshan; Jiang, Hualiang; European Journal of Medicinal Chemistry; vol. 145; (2018); p. 74 – 85;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 3144-09-0, 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. 3144-09-0, name is Methylsulfonamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Embodiment 80Under 80 C , the methanesulfonamide (0.75mmol, 71.3 mg) and (E) – 1,3-diphenyl-2-propen-1-ol (0.5mmol, 105.0 mg) and [BsTdmim]OTf (10mol %, 27.5 mg), 1,4-dioxane 2.0 ml is placed in a dry reaction flask, magnetic stirring reaction for 2h. After the completion of the reaction separation was done using column chromatography (by silica gel column, eluent: petroleum ether/ethyl acetate = 5/1), to obtain white solid (E)-N-(1,3-diphenylallyl)methanesulfonamide 142.1 mg, yield is 99%

The synthetic route of Methylsulfonamide has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Lanzhou Institute of Chemical Physics; Xia, Chungu; Han, Feng; Wang, Lei; Li, Zhen; (27 pag.)CN103073372; (2016); B;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 27466-83-7, 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. 27466-83-7, name is 4-Bromo-N-methylbenzamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Intermediate Preparation 154′-(2-(S)-Pyrrolidin-ylmethyl-pyrrolidine-1-carbonyl)-biphenyl-4-carboxylic acid methylamide Procedure Z’: To a stirring solution of 4-bromophenylmethyl amide (11.0 mmol, CAS No. 27466-83-7), bis-(pinacolato)diboron (1.1 mmol) and potassium acetate (3.0 mmol) in dimethyl sulfoxide (0.10M), add palladium(II) dichloride (dppf) complex with dichloromethane (1:1) (0.08 mmol). Heat reaction to 100 C. for 1.5 hours. After this time, cool the reaction to room temperature and add (4-bromo-phenyl)-(2-(S)-pyrrolidin-1-ylmethyl-pyrrolidin-yl)methanone (the product from preparation 14) (1.0 mmol), 2M aqueous sodium carbonate (3.0 mmol) add palladium(II) chloride (dppf) complex with dichloromethane (1:1) (0.08 mmol). Heat reaction to 100 C. for 18 hours. After this time, remove the heat and wash the reaction with water while extracting with 10% isopropanol/dichloromethane. Dry the organics with sodium sulfate, filter and concentrate in vacuo. Purify the title compound via radial chromatography eluting with 2M ammonia in methanol and dichloromethane. MS (m/e): 392.3 (M+1)

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

Reference:
Patent; Beavers, Lisa Selsam; Finley, Don Richard; Finn, Terry Patrick; Gadski, Robert Alan; Hipskind, Philip Arthur; Hornback, Wiliam Joseph; Jesudason, Cynthia Darshini; Pickard, Richard Todd; Takakuwa, Takako; Vaught, Grant Mathews; US2010/48580; (2010); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 25900-61-2, 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. 25900-61-2, name is 3-Amino-N-methylbenzamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 9; N-(2-Diethylamino-ethyl)-4-(3-indan-5-yl-3H-[1 ,2,3]triazolo[4,5-d]- pyrimidin-5-ylamino)-benzamide (7); To a solution of 2,4-dichloro-5-nitropyrimidine (25.0 mg, 0.13 mmol) in THF (0.2 mL) was added a solution of 3-amino-N-methyl-benzamide (19.5 mg, 0.13 mmol) in isopropyl alcohol (0.5 mL)/dimethylformarnide (0.3 mL), and CsHCO3 (25.2 mg, 0.13 mmol) in water (0.016 mL total volume). The mixture was stirred at rt for 1.5 hr at which time 4-amino-N-(2-diethylamino-ethyl)-benzamideEtaCl (procainamide hydrochloride) (38.9 mg, 0.14 mmol) in isopropyl alcohol (0.5 mL)/dimethylformamide (0.3 mL) was added. The mixture was stirred at 50C for 20 hr, cooled to rt, and acetic acid (0.1 mL) was added. To the resulting slurry was added Zn dust (45 mg, 0.69 mmol); after stirring for 15 min at rt, the reaction solution was loaded onto a 1 g silica gel SPE cartridge and eluted with 6 mL of MeOH. The eluent was concentrated at reduced pressure, dried at approximately 1 mm Hg for 18 hr, and re-suspended in MeOH (1.0 mL). To this slurry was added HOAc (0.05 mL) and sodium nitrite (0.09 g, 1.3 mmol) in water (total volume 0.2 mL). The mixture was stirred at rt for 11 hr, loaded onto a 1 g C-18 SPE cartridge, and eluted with 6 mL of MeOH. The eluent was concentrated and the resulting residue was purified by reverse-phase liquid chromatography using a gradient of 90:10 (water:acetonitrile, with 0.1% TFA) to 10:90 (wateracetonitrile, with 0.1% TFA) to furnish (7) (0.0128 g, 0.018 mmol) as the bis TFA salt. HRMS (ES-TOF) calcd. for C25H30N9O2 m/z 488.2522 (M+H),+ found: 488.2514

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

Reference:
Patent; JANSSEN PHARMACEUTICA N.V.; WO2006/76442; (2006); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 72505-21-6, 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. 72505-21-6 name is 4-(Trifluoromethyl)thiobenzamide, 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: A solution of 3-bromo-1-benzofuran-2(3H)-one (0.5 g,2.35 mmol) in toluene (5 mL) was added dropwise to a suspensionof the corresponding thioamide (2.35 mmol) and pyridine (65 mL,0.8 mmol) in toluene (5 mL) at room temperature. The reactionmixturewas stirred and heated at 80C for 2 h and then cooled. The amorphous precipitate was collected by filtration and thenrecrystallized from 80% aqueous ethanol to give products 1a-h as orange crystals. Alternative method for synthesis of 1a is alsodescribed in Ref. [25].

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

Reference:
Article; Kammel, Richard; Tarabova, Denisa; Machalicky, Old?ich; Nepra?, Milo?; Frumarova, Bo?ena; Hanusek, Ji?i; Dyes and Pigments; vol. 128; (2016); p. 101 – 110;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Related Products of 20348-09-8, 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. 20348-09-8, name is 2H-Pyrido[3,2-b][1,4]oxazin-3(4H)-one belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To 2H-pyrido[3,2-b][1 ,4]oxazin-3(4H)-one (45.0 g, 300 mmol) in DMF (360 mL) at 20 C was added NBS (74.7 g, 420 mmol) in one portion, and the resulting brownish suspension was heated at 50 C for 20 hours. The mixture was cooled to 25 C, and the content was poured into stirred water (1 L) in a 3 L flask fitted with an overhead mechanical stirrer. The resulting aqueous suspension was stirred at room temperature for 30 minutes followed by filtration. The yellowish cake was washed with 10% Na2S203 solution (100 mL) followed by water (2 x 100 mL). The cake was aspirated at room temperature under house vacuum overnight. The solids were washed with Et20 (100 mL), aspirated under house vacuum at room temperature for 18 hours, and then dried under high vacuum at 50 C for 72 hours to afford the title compound (65.30 g) as a light tan-colored powdery solid. LC-MS (ES) m/z = 229, 231 [M+H]+. 1H NMR (400 MHz, DMSO-d6): delta 4.68 (s, 2H), 7.66 (d, J = 2.0 Hz, 1 H), 8.02 (d, J = 2.0 Hz, 1 H), 1 1 .44 (br. s., 1 H).

The synthetic route of 2H-Pyrido[3,2-b][1,4]oxazin-3(4H)-one has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; MEDINA, Jesus Raul; TIAN, Xinrong; NG DI MARCO, Christina; GRAYBILL, Todd L.; HEERDING, Dirk A.; LI, William Hoi Hong; MANGATT, Biju; MARTYR, Cuthbert D.; RIVERO, Raphael Anthony; (570 pag.)WO2019/49061; (2019); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 5900-59-4,Some common heterocyclic compound, 5900-59-4, name is 2-Amino-4-chlorobenzamide, molecular formula is C7H7ClN2O, 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 A To a mixture of 0.34 g of 2-amino-4-chlorobenzamide, 0.57 g of monochloroacetic acid, 0.90 g of sodium iodide and 0.24 g of magnesium oxide was added 2 ml of dimethylformamide and the mixture was stirred at a temperature between 90¡ã and 100¡ã C. for 2.5 hours. After cooling, the reaction mixture was poured into 50 ml of a 2.6percent aqueous sodium carbonate solution. The resulting precipitates were filtered off and the filtrate was extracted with 50 ml of chloroform. The aqueous layer was acidified with concentrated hydrochloric acid to precipitate crystals. The crystals were collected by filtration and recrystallized from aqueous methanol to obtain 0.20 g of N-(2-carbamoyl-5-chlorophenyl)glycine as needles having a melting point of 217¡ã-222¡ã C. (decomposition). Elemental Analysis for C9 H9 O3 N2 Cl: Calcd.(percent): C, 47.28; H, 3.97; N, 12.25. Found (percent): C, 47.11; H, 3.74; N, 12.32.

The synthetic route of 5900-59-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Daiichi Seiyaku Co., Ltd.; US4297357; (1981); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 864448-41-9, These common heterocyclic compound, 864448-41-9, name is tert-Butyl 3-oxa-7,9-diazabicyclo[3.3.1]nonane-7-carboxylate, 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 solution tert-butyl 3-oxa-7,9-diazabicyclo[3.3.1]nonane-7-carboxylate (400mg, L75 mmol) and Et3N (0.49 niL, 3.5 mrnol) in DCM (10 mL) was added CbzCl (448 mg, 2.63 mmoi) at room temperature. The reaction mixture was stirred at room temperature for 2 hours and then water (10.0 mL) was added, and the mixture is extracted three times with EtOAc (30 rnL each). The combined organic phase was dried over Na2SO4 and concentrated. The residue was purifiedby silica gel colunm chromatography (PE: EtOAc, from 10:1 to 2: 1) to give a white solid (300 mg). The solid was dissolved in ACN (8 mL) and water (2 rnL), to which were added RuC13 (35 mg, 0.170 mmol) and Na104 (532 mg, 2.48 mmoi). The reaction mixture was stirred at room temperature for 36 hours and water (10 niL) was added, and the mixture was extracted three times with EtOAc (20 mL), The combined organic phase was dried over Na2SO4 andconcentrated. The residue was purified by column (PE: EtOAc, from 10:1 to 1: 1) to give the desired product 13a as a yellow oil (150 mg). LCMS (M-100+H) 277.1

The synthetic route of 864448-41-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; HU, Taishan; KOU, Buyu; LIU, Haixia; ZHANG, Zhisen; ZHOU, Zheng; (54 pag.)WO2018/11162; (2018); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Related Products of 16982-21-1,Some common heterocyclic compound, 16982-21-1, name is Ethyl 2-amino-2-thioxoacetate, molecular formula is C4H7NO2S, 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 1-bromo-3-methylbutan-2-one (1.1 g, 6.66 mmol), ethyl thioxamate (600 mg, 4.51 mmol) in 5.0 mL ethanol was refluxed overnight. After the completion of the reaction the solvent was removed and the crude mixture was dissolved in ethyl acetate. The organic layer was washed with water, brine and was dried under sodium sulfate. Evaporation of the solvent produced the desired product mixed with impurities which was used for the next step without further purification (400 mg, 30% yield).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Ethyl 2-amino-2-thioxoacetate, its application will become more common.

Reference:
Patent; LaVoie, Edmond J.; Parhi, Ajit; Pilch, Daniel S.; Zhang, Yongzheng; Kaul, Malvika; US2015/133465; (2015); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Related Products of 125414-41-7, 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 125414-41-7 as follows.

2-(tert-butoxycarbonylamino)propane-l ,3-diyl ditetradecanoate To a solution of tetradecanoic acid (1.051 g) in dichloromethane (10 mL) at 00C were added tert-butyl l,3-dihydroxypropan-2-ylcarbamate (0.40 g), 4-(dimethylamino)pyridine (0.562 g), N-methylmorpholine (1.150 mL), and l-ethyl-3-(3-(dimethylamino)propyl)carbodiimide hydrochloride (0.882 g). The mixture was stirred at room temperature overnight. The mixture was partitioned between water and dichloromethane. The aqueous layer was extracted with dichloromethane. The extract were dried over Na2SO4, filtered, and concentrated. The concentrate was purified by flash chromatography (1 :10 ethyl acetate/hexanes). MS (ESI) m/z 512.4 (M-CO2-tert-butyl+l)+.

According to the analysis of related databases, 125414-41-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ABBOTT LABORATORIES; WO2009/129385; (2009); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics