Author: tianli

Adding some certain compound to certain chemical reactions, such as: 4093-29-2, name is Methyl 4-acetamido-2-methoxybenzoate, 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 4093-29-2. 4093-29-2

[0543] To a solution of 269-3 (4.46 g, 20 mmol), PdOAc (0.45 g, 2 mmol) and Cu(OAe)2 (7.26 g, 40 mmol) in 1.2-dichloroethane ( 150 mL) was added anhydrous CuBr2 (8.93 g. 40 mmol) under N2 atmosphere. The mixture was stirred at 90 C for 72 h. After cooling to r.t., the reaction was quenched by water, and filtered through a celite pad. The solution was washed with brine, dried by anhydrous Na2S04 and concentrated at low pressure. The residue was purified by flash column chromatography on silica gel (PE:EA 1 : 1 ) to give 269-4 (6.04 g, 51 .3%). +ESI-MS:m/z 303.7 [M+I I]

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 Methyl 4-acetamido-2-methoxybenzoate.

Reference:
Patent; ALIOS BIOPHARMA, INC.; WANG, Guangyi; BEIGELMAN, Leonid; TRUONG, Anh; NAPOLITANO, Carmela; ANDREOTTI, Daniele; HE, Haiying; STEIN, Karin, Ann; WO2015/26792; (2015); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

1746-77-6, These common heterocyclic compound, 1746-77-6, name is Isopropyl 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.

Intermediate 491 -methylethyl (2E)-2-butenoylcarbamateIsopropyl carbamate (30 g, 291 mmol, available from TCI) was charged to a 3L Lara vessel and dry Tetrahydrofuran (THF) (150 ml) added. (2E)-2-butenoyl chloride (31.2 ml, 326 mmol, available from Aldrich) was added under nitrogen and the jacket cooled to – 30C. When the solution temperature reached -17C 1 M Lithium tert-butoxide (655 ml, 655 mmol) was added by peristaltic pump over 2 hours, keeping the reaction temperature between -10C and -18C. Once the addition was complete the mixture was complete the mixture was stirred for 30 mins and brought to 0C. Diethyl ether (450ml) and 1 M HCI (375ml) were added and the mixture brought to 20C with vigourous stirring. The stirring was stopped, the layers allowed to separate and the aqueous layer run off. Brine (375ml) was added and the mixture stirred vigourously. The stirring was stopped, the layers allowed to separate and the aqueous layer run off. The organic layer was dried (magnesium sulfate), filtered and evaporated to a brown oil (60g). The mixture was loaded on to a 40+M Biotage silica column and eluted with DCM:ethyl acetate (1 :1 to 0:1 , 10CV). The product containing fractions were evaporated to dryness and loaded on to a 1500g Redisep Isco silica column and eluted with a gradient of 0 to 40% ethyl acetate in cyclohexane. The clean, product containing fractions were evaporated to an off white solid (15.41 g). LCMS (Method C): Rt = 0.68 , MH+ = 172

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 1746-77-6.

Reference:
Patent; GLAXOSMITHKLINE LLC; DEMONT, Emmanuel, Hubert; GARTON, Neil, Stuart; GOSMINI, Romain, Luc, Marie; HAYHOW, Thomas, George, Christopher; SEAL, Jonathan; WILSON, David, Matthew; WOODROW, Michael, David; WO2011/54841; (2011); 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. 4664-01-1 name is 3,4-Pyridinedicarboximide, 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. 4664-01-1

NaOH (10% aqueous, 640 ml) was cooled to 7 C. and bromine (15 ml, 286.82 mmol) added dropwise. Pyrrolo[3,4-c]pyridine-1,3-dione (41.711 g, 281.6 mmol) was then added to the reaction mixture before it was heated to 80 C. for 30 minutes. After this time the reaction was allowed to warm to 37 C. and the pH modified to 5.5 by the addition of acetic acid (70 ml). A suspension formed that was removed by filtration and washed with 20 ml of ice cold methanol to give the title compound (26.58 g, 68.33%) in a suitably clean form to be used without any further purification. m/z (LC-MS, ESP): 139 [M+H]+, R/T=0.72 mins.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3,4-Pyridinedicarboximide, and friends who are interested can also refer to it.

Reference:
Patent; Kudos Pharmaceuticals Ltd; US2006/199804; (2006); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

7341-96-0,Some common heterocyclic compound, 7341-96-0, name is Propiolamide, molecular formula is C3H3NO, 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: 2-Azanorbornene 1 (2 mmol) was dissolved in dry CHCl3 (15mL) at ambient temperature, then the substituted acetylene (2.2 mmol) was added to the solution and the homogenous mixture stirred at r.t (24 h for MP and PA; 72 h for dialkyl acetylene dicarboxylates; TLC monitoring). Evaporationof the solvent under reduced pressure gave a crude brown oil which was purified by silica gel column chromatography (hexane-EtOAc with increasingpolarity as eluent) to provide products 2-4 as colorless oils or white powders. In the case of the reaction with MP, the obtained products 2a-e were unstable at r.t in air (quickly became dark), but relatively stable under a N2 atmosphere at -16 C.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 7341-96-0, its application will become more common.

Reference:
Article; Nasirova, Dinara K.; Malkova, Anastasia V.; Polyanskii, Kirill B.; Yankina, Kristina Yu.; Amoyaw, Prince N.-A.; Kolesnik, Irina A.; Kletskov, Alexey V.; Godovikov, Ivan A.; Nikitina, Eugeniya V.; Zubkov, Fedor I.; Tetrahedron Letters; vol. 58; 46; (2017); p. 4384 – 4387;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

These common heterocyclic compound, 563-83-7, name is Isobutyramide, 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. 563-83-7

Compound 119 (10 g, 0.11 mol) , Lawson’s reagent (24 g, 0.06 mol) was added to a round bottom flask containing 150 mL of anhydrous tetrahydrofuran, protected with nitrogen, and stirred at 70 for 16 h. LCMS monitoring, after the reaction was completed, quenched with saturated sodium bicarbonate solution, extracted with EtOAc (400 mL ¡Á 2) , and the combined extracts were washed with saturated aqueous sodium chloride (100 mL) , dried with anhydrous Na 2SO 4, concentrated under reduced pressure, and then purified by column chromatography (eluent: ethyl acetate/petroleum ether, 1/3, v/v) , obtained 5 g of a yellow soild, yield: 42.4%. 1H NMR (400 MHz, CDCl 3) : delta ppm 1.29 (d, J = 6.8 Hz, 6H) , 2.84-2.97 (m, 1H) , 6.95 (s, 1H) , 7.73 (s, 1H) . LCMS: Rt = 0.82 min, MS Calcd.: 103.0, MS Found: 104.2 [M+H] +

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 563-83-7.

Reference:
Patent; ZHUHAI YUFAN BIOTECHNOLOGIES CO., LTD; LIAO, Xuebin; (208 pag.)WO2019/206049; (2019); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

6292-59-7, name is 4-(tert-Butyl)benzenesulfonamide, 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. 6292-59-7

Example 5 A solution of 1 g of 2-(1,3-benzodioxol-5-yl)-2-(1,3-dihydro-1,3-dioxoisoindol-5-yloxy)acetic acid and 0.71 g of carbonyldiimidazole in 100 ml of THF is heated at 60¡ã for 2 hours. 0.93 g of 4-tert-butylbenzenesulfonamide and 0.67 g of 1,8-diaza-bicyclo[5.4.0]-undec-7-ene are then added and the mixture is stirred for a further 1 hour at this temperature. After customary working up, 2-(1,3-benzodioxol-5-yl)-2-(1,3-dihydro-1,3-dioxo-isoindol-5-yloxy)-N-(4-tert-butylphenylsulfonyl)acetamide, m.p. 215¡ã, is obtained.

Statistics shows that 6292-59-7 is playing an increasingly important role. we look forward to future research findings about 4-(tert-Butyl)benzenesulfonamide.

Reference:
Patent; Merck Patent Gesellschaft mit Beschrankter Haftung; US5821256; (1998); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding some certain compound to certain chemical reactions, such as: 83948-53-2, name is tert-Butyl N-(3-Bromopropyl)carbamate, 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 83948-53-2. 83948-53-2

The synthesis of the second key synthon 23 is described in scheme 2. This synthon will bear a masked (Boc protecting group) amine function enabling for example a bioconjugation reaction with an antibody or a biomolecule. The compound 17 was prepared according to the procedures descrinbed in the literature (WO 2014/111661). The diol 8 is activated in ditosylate form then condensed with the compound 19 resulting in the compound 21 with a good yield. The Sonogashira reaction followed by the deprotection of the nosy group enables the synthon 23 to be obtained.

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 tert-Butyl N-(3-Bromopropyl)carbamate.

Reference:
Patent; CISBIO BIOASSAYS; UNIVERSITE PAUL SABATIER; CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE; LAMARQUE, Laurent; PICARD, Claude; GALAUP, Chantal; LEYGUE, Nadine; ZWIER, Jurriaan; BOURRIER, Emmanuel; (48 pag.)US2018/362549; (2018); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

109903-35-7, Adding a certain compound to certain chemical reactions, such as: 109903-35-7, name is 4-Amino-N-methylbenzenemethanesulfonamide, 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 109903-35-7.

4-Amino-3-iodo-N-methylbenzenemethanesulfonamide To a suspension of 1.06 g (5.31 mmol, 1.0 equiv.) of 4-amino-N-methylbenzenemethanesulfonamide in 20 mL of acetonitrile was added 0.862 g (5.31 mmol, 1.0 equiv.) of iodine monochloride. The reaction was stirred for 15 minutes at room temperature. The mixture was partitioned between 25 mL of ethyl acetate and 15 mL of 20% aqueous sodium thiosulfate. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to yield an oil. The oil was filtered through a plug of silica gel using 40% ethyl acetate in hexane to yield 1.13 g (65%) of 4-amino-3-iodo-N-methylbenzenemethanesulfonamide.

According to the analysis of related databases, 109903-35-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Bristol-Myers Squibb Company; US5434154; (1995); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

16982-21-1, 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 16982-21-1 as follows.

To a boiling solution of ethyl thiooxamate (13,3 g ,10Og, 100 mmol) in ethanol (100 mL) was added l-bromo-3-methylbutan-2-one (17,6 g ,g, 106 mmol) dropwise during 15 minutes. The solution was refluxed for one hour. The solution was added to 250 mL of ice-cold water and basified with concentrated ammonia solution. This mixture was extracted twice with AcOEtethyl acetate. The organic phase was washed with brine, dried (Na2SO4) and evaporated under reduced pressure. The crude product was purified by column chromatography with dichloromethane to dichloromethane with 2% MeOH methanol to give 13,1 g (65%) of the target product: 1H-NMR-CDCl3: 7,20 (s, IH), 4,49 (m, 2H), 3,25 (m, IH), 1,42 (t, 3H), 1,35 (d, 6H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 16982-21-1, and friends who are interested can also refer to it.

Reference:
Patent; TIBOTEC PHARMACEUTICALS LTD.; MEDIVIR AB; WO2007/14921; (2007); A1;,
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 4093-31-6 as follows. 4093-31-6

Stage B Preparation of 4-amino-5-chloro-2-methoxybenzoic acid Methyl 4-acetamido-5-chloro-2-methoxybenzoate is dissolved in ethanol and aqueous potassium hydroxide added. The solution is refluxed for a short time, cooled and concentrated hydrochloric acid added. The resulting precipitate is filtered off, washed with water and dried to give the title compound as a white solid.

According to the analysis of related databases, 4093-31-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Palmer, Richard Michael John; Meyers, Nicholas Leslie; Knight, John; US2005/49416; (2005); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics