Tag: M.W=200-300

Adding a certain compound to certain chemical reactions, such as: 94838-59-2, name is tert-Butyl 4-aminophenethylcarbamate, 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 94838-59-2, Computed Properties of C13H20N2O2

Tert-butyl (4-aminophenethyl)carbamate (4.5 g, 21.83 mmol, 1.0 eq) was dissolved in DCM (150 mL) and cooled to 0C using an ice bath. DMAP (1.6 eq) was added in one portion to the stirring mixture followed by dropwise addition of bromoacetyl bromide (1.2 eq) in 50 mL DCM. The mixture was stirred for 30 minutes at 0C and then 1.5 hours at room temperature before it was concentrated in vacuo. The crude material was purified using column chromatography on Si02 with 75-100% EtOAc in heptane as eluent. This gave a colorless solid which was used directly in the next example.

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Reference:
Patent; UNIVERSITETET I OSLO; GOLDING, Louise; RONGVED, Pal; ASTRAND, Ove Alexander H°gmoen; SAMUELSEN, Ørjan; SCHNAARS, Christian; KILDAHL-ANDERSEN, Geir; (234 pag.)WO2018/33719; (2018); A1;,
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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. 162787-61-3, name is 2-(Methylsulfonamido)benzoic acid, A new synthetic method of this compound is introduced below., Formula: C8H9NO4S

In a separate reaction vessel, O-Benzoic acid methanesulfamide(0.039g, 0.183 mmol),HATU(0.1 16g, 0.305 mmol), and pyridine(29ul, 0.366 mmol), were dissolved in anhydrous DMF (5 ml). The reaction mixture was stirred under nitrogen for 2 hours to activate the acid. When activation was approximately 80% complete by LC/MS (2 hr) the piperidine solution in DMF (0.028g, 0.121 mmol), along with DIPEA (86ul, 0.488mmol) were added. The reaction was stirred overnight while monitoring by LC/MS. Solvents were removed by rotary evaporation. The residue was taken up in DCM (100 ml)and washed with water (5 x 100 ml). The organic layer was collected, dried over MgS04, filtered and evaporated. The residue was taken up in DCM and columned on silica gel using a gradient of 0 to 10% MeOH to provide compound 18 : DCM. (Yield- 32.45 mg, 0.076 mmol, 62 %).1H-NMR (CD3CN, 300 MuEtazeta):delta 1.50 (m, 2H), 1.74 (m, 1H), 2.20 (bs, 1H), 2.31 (s, 3H), 2.43 (s, 1H), 2.99 (s, 3H), 3.10 (m, 1H), 3.35 (m, 1H), 6.22-6.46 (m, 1H), 7.25-7.70 (m, 4H), 8.80- 9.00 (m, 1H).

The synthetic route of 162787-61-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GILEAD SCIENCES, INC.; BABAOGLU, Kerim; BOOJAMRA, Constantine, G.; EISENBERG, Eugene, J.; HUI, Hon Chung; MACKMAN, Richard, L.; PARRISH, Jay, P.; SANGI, Michael; SAUNDERS, Oliver, L.; SIEGEL, Dustin; SPERANDIO, David; YANG, Hai; WO2011/163518; (2011); A1;,
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Electric Literature of 24036-52-0,Some common heterocyclic compound, 24036-52-0, name is 6-Bromo-2H-1,4-benzoxazin-3(4H)-one, molecular formula is C8H6BrNO2, 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: Toluene (4.5mL) was added to a flask containing 6-bromo-3,4-dihydroquinolin-2(1H)-one (300mg, 1.33mmol), 3-(trifluoromethoxy)aniline (231muL, 1.73mmol), Pd2(dba)3 (15.2mg, 0.02mmol), 2-dicyclohexylphosphino-2?,4?,6?-triisopropylbiphenyl (31.6mg, 0.07mmol) and NaOt-Bu (192mg, 2.00mmol) under an argon atmosphere. The mixture was stirred at 100C for 9h. After cooling, the reaction mixture was diluted with EtOAc, and filtered through a pad of Celite. The filtrate was concentrated in vacuo. Crude material was purified by flash chromatography with n-hexane/EtOAc (2:3) to afford the desired diaryl amine 11i

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6-Bromo-2H-1,4-benzoxazin-3(4H)-one, its application will become more common.

Reference:
Article; Takeuchi, Tomoki; Oishi, Shinya; Kaneda, Masato; Misu, Ryosuke; Ohno, Hiroaki; Sawada, Jun-Ichi; Asai, Akira; Nakamura, Shinya; Nakanishi, Isao; Fujii, Nobutaka; Bioorganic and Medicinal Chemistry; vol. 22; 12; (2014); p. 3171 – 3179;,
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These common heterocyclic compound, 79722-21-7, name is tert-Butyl benzyloxycarbamate, 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. Computed Properties of C12H17NO3

General procedure: Nucleophile (1-3 mol equiv), tris-(dibenzylideneacetone)dipalladium (2.5 mol %), tris-(2-furyl)phosphine (10 mol %) and potassium carbonate (2 mol equiv) were added to a solution of the aryl halide (1 mmol) in dry dimethylformamide (10 mL) in a Schlenk tube. The reaction mixture was then degassed using the freeze, pump, thaw (F.P.T.) technique (one cycle). Allene gas was then introduced at the required pressure (1 atm) and the Schlenk tube contents stirred and heated at 80 C for 16 h. After cooling and venting, DCM (20 mL) was added and the mixture filtered to remove inorganic salts. The filtrate was concentrated in vacuo and the residue was purified by column chromatography.

The synthetic route of tert-Butyl benzyloxycarbamate has been constantly updated, and we look forward to future research findings.

Reference:
Article; Elboray, Elghareeb E.; Gao, Chuanjun; Grigg, Ronald; Tetrahedron; vol. 68; 14; (2012); p. 3103 – 3111;,
Amide – Wikipedia,
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Electric Literature of 1012884-46-6,Some common heterocyclic compound, 1012884-46-6, name is 11-Chloro-2-methyl-2,3-dihydro-1H-dibenzo[2,3:6,7]oxepino[4,5-c]pyrrol-1-one, molecular formula is C17H12ClNO2, 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.

Magnesium metal turnings (10 g) were added to a suspension of 11-chloro-2-methyl-2,3-dihydro-1H-dibenzo[2,3:6,7]oxepino[4,5-c]pyrrol-1-one (7 g) in methanol (50 mL). The reaction mixture was slowly heated to refluxing temperature. Brisk effervescence was observed. The reaction mixture was cooled to control the reaction and again refluxed for about 2 hours. The reaction mass was diluted with methanol (30 mL), further refluxed for about 30 minutes, cooled to ambient temperature, slurried in water (150 mL) and filtered. pH of the filtrate was adjusted to 1-2 by adding concentrated hydrochloric acid. A clear solution was obtained. The solution was extracted with ethyl acetate (3x50mL) followed by washing with water (3×50 mL). Ethyl acetate was recovered to obtain a mixture of diastereomers as brown oil (4.6 g) followed by separation of the two isomers using silica gel column chromatography eluting with ethyl acetate-hexane mixture. cis-isomer: 50% trans-isomer 9%

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 11-Chloro-2-methyl-2,3-dihydro-1H-dibenzo[2,3:6,7]oxepino[4,5-c]pyrrol-1-one, its application will become more common.

Reference:
Patent; RANBAXY LABORATORIES LIMITED; ARYAN, Ram Chander; MISHRA, Anamika; NAIDU, Pudi, Giri, J.; SHARMA, Ramnik; WO2013/11461; (2013); A1;,
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. 201162-53-0, name is 3-Boc-3,8-Diazabicyclo[3.2.1]octane, This compound has unique chemical properties. The synthetic route is as follows., Safety of 3-Boc-3,8-Diazabicyclo[3.2.1]octane

tert-butyl 3,8- diazabicyclo[3.2.ljoctane-3-carboxylate (500 mg, 2.36 mmol) was dissolved in methanol (9 ml) for the addition of hydrochloric acid (4 M in dioxane, 2.95 mL, 11.8 mmol). The reaction mixture was stirred 16 h, then concentrated in vacuo and dried under high vacuum to afford the title compound (0.44 g, 2.38 mmol) in quantitative yield. LCMS MZ (M+H) 113.

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 201162-53-0.

Reference:
Patent; GENENTECH, INC.; CONSTELLATION PHARMACEUTICALS, INC.; ALBRECHT, Brian, K.; COTE, Alexandre; CRAWFORD, Terry; DUPLESSIS, Martin; GOOD, Andrew, Charles; LEBLANC, Yves; MAGNUSON, Steven, R.; NASVESCHUK, Christopher, G.; ROMERO, F. Anthony; TANG, Yong; TAYLOR, Alexander, M.; (271 pag.)WO2016/138114; (2016); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 141449-85-6, A common heterocyclic compound, 141449-85-6, name is tert-Butyl hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate, molecular formula is C11H20N2O2, 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.

According to Synthetic Method 2: 2-bromo-4-methylthiazole-5-carboxylic acid ethyl ester (2.592 g, 10.36 mmol),Hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylic acid tert-butyl ester (2.000 g, 9.42 mmol), sodium carbonate (2.51 g, 23.6 mmol) and acetonitrile (40 mL) were added to a 100 mL reaction flask The reaction was carried out under reflux at 80 C for 4 hours.The reaction was completed by TLC and the reaction was stopped. Cool to room temperature, spin dry, purified by silica gel column ( petroleum ether / ethyl acetate (v / v) = 3 / 1), concentrated and dried to give the title compoundThe material was a pale yellow solid (2.70 g, yield: 75.1%).

The synthetic route of 141449-85-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Jin Chuanfei; Xu Tengfei; Zhang Yingjun; Xue Yaping; (33 pag.)CN109956945; (2019); A;,
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Amide – an overview | ScienceDirect Topics

Some common heterocyclic compound, 33045-52-2, name is Methyl 2-methoxy-5-sulfamoylbenzoate, molecular formula is C9H11NO5S, 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. COA of Formula: C9H11NO5S

EXAMPLE 23 N-(1-cyclopentyl-2-pyrrolidinyl-methyl)-2-methoxy-5-sulphamoyl-benzamide 23 g of methyl 2-methoxy-5-sulphamoyl benzoate (0.09 mole) is dissolved hot, at about 90 C., in 115 ml of glycol in a 500 ml flask fitted with an agitator and a thermometer. The solution is cooled to 50 C. and the ester re-crystallises. 19 g of 1-cyclopentyl-2-amino-methyl-pyrrolidine is added. The suspension obtained is kept at 50 C. After 30 hours the ester is completely dissolved. The solution continues to be heated until a sample taken is found to be completely soluble in acetic acid. The solution is then cooled and the benzamide crystallises slowly. 150 ml of water is added and the precipitate is drained, washed with water and dried. 23 g (68%) of benzamide is obtained with a melting point of 147-148 C.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 33045-52-2, its application will become more common.

Reference:
Patent; Societe d’Etudes Scientifiques et Industrielle de l’Ile de France; US4673686; (1987); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 40724-47-8, These common heterocyclic compound, 40724-47-8, name is 4-Bromomethylbenzenesulfonamide, 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.

In this example, Compound 1 of the Scheme 2 is coupled with compound 2 of Scheme 2 at the presence of an activating agent BOP to give product 3 of Scheme 2, which then alkylated with substituted benzyl bromide 4 of Scheme 2 to produce the desired product 6 of Scheme 2 and by product 5 of Scheme 2. Compound 6 of Scheme 2 is purified by a silica gel column and then reacted with TFA to cleave the Boc group. Compound 7 of Scheme 2 is alkylated with benzyl bromide, and the reaction mixture is purified by HPLC to yield final product compound of Formula I, which in the exemplified scheme is a white solid with purity >98percent, overall yield about 32percent.

Statistics shows that 4-Bromomethylbenzenesulfonamide is playing an increasingly important role. we look forward to future research findings about 40724-47-8.

Reference:
Patent; INTRA-CELLULAR THERAPIES, INC.; LI, Peng; PENG, Youyi; TOMESCH, John; WENNOGLE, Lawrence P.; ZHANG, Qiang; (15 pag.)US2018/333403; (2018); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

1103234-56-5, name is 2,6-Difluoro-3-(propylsulfonamido)benzoic acid, 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. Recommanded Product: 2,6-Difluoro-3-(propylsulfonamido)benzoic acid

Example 4Propane-1 -sulfonic acid {3-[5-(4-chloro-phenyl)-1 H-pyrrolo[2,3-b]pyridine-3-carbonyl]- 2,4-difluoro-phenyl}-amide (1 )A suspension of sulfonamide acid (9) (1 .2 eq.) in CH2CI2 was treated at roomtemperature with cat. amount of DMF (0.1 1 eq.). Within 30 min a solution ofoxalylchloride (1 .30 eq.) in CH2CI2 was added and the reaction mixture was stirred for 2 h, whereby the corresponding acid chloride was formed. A suspension of aluminium chloride (AICI3, 4 eq.) in CH2CI2 was treated at 0C with a solution of Cl-phenyl azaindole (8) in CH2CI2. To the reaction mixture was subsequently added at room temperature the freshly prepared (above described) acid chloride. Stirring at room temperature for 3 h, aqueous work-up and crystallization from THF/heptane provided the title compound (1 ) as off-white powder in 85% yield. MS (Turbo Spry): 509 (48%), 507 (M+NH4+, 100%), 492 (40%), 490 (M+H+, 84%).

The synthetic route of 1103234-56-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; BRUMSTED, Corey James; MOORLAG, Hendrik; RADINOV, Roumen Nikolaev; REN, Yi; WALDMEIER, Pius; WO2012/10538; (2012); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics