Category: amides-buliding-blocks

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;,
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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;,
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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;,
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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;,
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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,
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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;,
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17193-28-1, These common heterocyclic compound, 17193-28-1, name is 1-Amino-1-cyclopentanecarboxamide, 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.

EXAMPLE 1 2-butyl-1,3-diaza-spiro[4,4]non-1-en-4-one-monohydrochloride 20 g (0.156 mol) of 1-aminocyclopentane-1-carboxamide and 31 g (0.19 mol) of trimethyl orthovalerate are refluxed at 70-80 C. inner temperature for 1 hour. The condenser is then changed to a “No hold up” condenser, while heating and stirring are continued to distille off volatile components. The reaction is completed in vacuo. The residue is dissolved in 150 ml of acetone the pH is adjusted to 1-2, after cooling the resulting suspension the product is filtered off. 31 g of the title compound is obtained, yield 86.4%. IR: 3600-2200: vibr, NH; 1779: gammac=o; 1642 gammac, 1517: deltaNH (IRFT Perkin Elmer)

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 17193-28-1.

Reference:
Patent; Sanofi-Synthelabo; US6162923; (2000); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

127828-22-2,Some common heterocyclic compound, 127828-22-2, name is tert-Butyl (2-(2-aminoethoxy)ethyl)carbamate, molecular formula is C9H20N2O3, 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 2-(2-aminoethoxy)ethylcarbamate (570 mg, 2.8 mmol) was taken up in CH3CN (8 mL) and DMF (8 mL) along with Acipimox (435 mg, 2.8 mmol) HATU (1.17 g, 3.1 mmol) and DIEA (730 muL, 4.2 mmol). The resulting reaction mixture was stirred at room temperature for 18 h. It was then diluted with EtOAc (50 mL), washed with water (3*10 mL), brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (9:1 CH2Cl2/MeOH) to afford 5-((2-(2-((tert-butoxycarbonyl)amino)ethoxy) ethyl)carbamoyl)-2-methylpyrazine 1-oxide (810 mg, 85%).

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 (2-(2-aminoethoxy)ethyl)carbamate, its application will become more common.

Reference:
Patent; Milne, Jill C.; Jirousek, Michael R.; Bemis, Jean E.; Vu, Chi B.; US2011/82156; (2011); A1;,
Amide – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 283173-80-8, name is 2-Bromo-8-fluoro-4,5-dihydro-1H-azepino[5,4,3-cd]indol-6(3H)-one, 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 283173-80-8, 283173-80-8

l, r-Bis(diphenylphosphino)ferrocene palladium (II) dichloride (2.5 moles, 1.83 kg) was added to a solution of Formula-Al (1.0 moles) in a 1:2 mixture of 4.2 L of dichloromethane and degassed dimethylacetamide. The reaction mass was stirred for 1 hour at about 20 C. Thereafter, the reaction mixture temperature was raised to 95 C and stirred for 1 hour. In a separate vessel, Formula-C3 (1.2 moles) was dissolved in dimethylacetamide (1.1 L) and added to 2.8 L of an aqueous solution of sodium carbonate (2.0 moles) and stirred for 3 hours at 20 C. The contents of the separate vessel were added to the first reaction mixture, maintaining the temperature above 90 C. The combined reaction mixture was stirred for 2 hours, cooled to room temperature, and further stirred for 4 hours. Water (2.8 L) was added to the reaction mixture which was filtered. The obtained solid was crystallized in methanol to obtain a compound of Formula-B 1.

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, 2-Bromo-8-fluoro-4,5-dihydro-1H-azepino[5,4,3-cd]indol-6(3H)-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MYLAN LABORATORIES LTD; JAYACHANDRA, Sureshbabu; SETHI, Madhuresh; KAUSHIK, Vipin Kumar; RAVI, Vijaya, Krishna; TELAGAMSETTY, Bhaskar Kumar; (44 pag.)WO2019/130229; (2019); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics