Amides-buliding-blocks

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. 621-38-5, name is 3-Bromoacetanilide, A new synthetic method of this compound is introduced below., 621-38-5

Step 1: To DMF (16 mL) was added POCI3 (48.8 mL. 523 mmol) dropwise via cannula over 30 minutes at 0 C. and the reaction mixture was stirred for another 30 minutes at this temperature. Then, N-(3-brornophenyi)acetamide (16 g, 75 minol) was added to the mixture and the reaction was stirred at 80 C for 2 It The solvent was then removed under reduced pressure to afford crude residue which was diluied with 200 mL of saturated aqueous NaHCO3 and extracted with1000 inL of EtOAc. The organic phase was washed with water (600 mL), brine (300 mL), dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluted with 20% EtOAc/PE) to afford 7-brorno-2.-chloroquinoline-3-carbaldehyde as a solid. Then, 7-bromo-2- cliloroquinoline-3-carbaldehyde (1.8 g, 6.65 mmol) was coevaporated with toluene (5 rnL) threetimes. To a. solution of 7-brorno-2-chloroquinohne-3-carbaldehvde (1.8 g, 6.65 mmol) in DCM(27 ni) was added DAST (1.76 mL, 13.31 mmol) at 0 C, and the nixiure was then stuffed at50 C for 1.5 h. The reaction was diluted with 50 rnL of saturated aqueous Nal-{C03 at 0 C andextracted with 250 rnL EtOAc. The organic phase was washed with water (100 mL), brine (100mL), dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated underreduced pressure. The resulting residue was purified by silica gel column chromatography(eluted with 30% DCM/PE) to afford 7-brorno-2-chloro-3-(difluorornethyl)quinoline as a solid.MS: 292/294 (M ¡À 1/M ¡À 3).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; MERCK SHARP & DOHME CORP.; IDENIX PHARMACEUTICALS LLC; MACHACEK, Michelle; WITTER, David; GIBEAU, Craig; HUANG, Chunhui; KAWAMURA, Shuhei; SLOMAN, David, L.; SILIPHAIVANH, Phieng; QUIROZ, Ryan; WAN, Murray; SCHNEIDER, Sebastian; YEUNG, Charles, S.; REUTERSHAN, Michael, H.; HENDERSON, Timothy, J.; PAPARIN, Jean-Laurent; RAHALI, Houcine; HUGHES, Jonathan, M., E.; SANYAL, Sulagna; YE, Yingchun; CANDITO, David, A.; FIER, Patrick, S.; SILVERMAN, Steven, M.; (277 pag.)WO2020/33288; (2020); A1;,
Amide – Wikipedia,
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27366-72-9, 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. 27366-72-9, name is 2-(Dimethylamino)ethanethioamide hydrochloride, This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 10 Preparation of N-4-(2-dimethylaminomethyl-4-thiazolyl)butyl-N’-methyl 2-nitro-1,1-ethenediamine. Following the procedure of Example 1, a stirred solution containing 3.2 g. of dimethylaminothioacetamide hydrochloride, and 6.48 g of bromomethyl 4-phthalimidobutyl ketone [prepared by the procedure of Chem. Listy., 49, 1385 (1955); C.A., 50, 5573c (1956)]; in 50 ml. of ethanol was heated at refluxing temperature for about 5 hours and was then cooled. Volatile constituents were removed by evaporation in vacuo leaving 2-dimethylaminomethyl-4-(4-phthalimido-1-butyl)thiazole as a semi-solid residue. The compound was utilized without further purification. A solution was prepared containing the above product in 50 ml. of methanol.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Eli Lilly and Company; US4382090; (1983); A;,
Amide – Wikipedia,
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61903-11-5, 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 61903-11-5 as follows.

(e). 1-{4-[1-(4-Fluoro-phenyl)-8,9-dimethoxy-5,6-dihydro-imidazo[5,1-a]isoquinoline-3-carbonyl]-[1,41]diazepan-1-yl}-ethanone; hydrochloride salt A solution of the product of 50d (60 mg) in dioxane (1 ml) was treated with a solution of LiOH (20 mg) in water (0.3 ml). The mixture was stirred for 45 min and neutralized by addition of an aqueous HCl solution (0.5 N). The aqueous material was freeze-dried and diluted with DMF (1 ml). N-acetylhomopiperidine (30 mg), N-ethylmorpholine (30 ml) and TBTU (60 mg) were added. The reaction mixture was stirred for 4 h, poured in water and extracted with ethyl acetate. The organic layer was dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by chromatography on silica gel (dichloromethane/acetone as eluent). The product was dissolved in a mixture of acetone/ether (v:v, 1:1) and treated with one equivalent of a 0.4N HCl solution in ether. Yield: 10 mg. MS-ESI: [M+H]+=493.4; TLC Rf=0.50 (dichloromethane/acetone 1:1); NMR (DMSO-d6) delta 2.00 (m, 3, acetyl(rotamers)), 3.47 and 3.80 (2*s, 6, OCH3), 6.95 and 7.02 (2*s, 2, H7 and H10), 7.30 and 7.69 (2*m, F-Ar-H); 19F-NMR (DMSO-d6)-114.9; hFSHRago (CHO luc) EC50=315 nM.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 61903-11-5, and friends who are interested can also refer to it.

Reference:
Patent; N.V. Organon; US2010/324021; (2010); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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. 51-06-9, name is 4-Amino-N-(2-diethylaminoethyl)benzamide, A new synthetic method of this compound is introduced below., 51-06-9

To a solution of procainamide (26 mg, 0.112 MMOL) in DICHLOROMETHANE (1.5 mL) under inert atmosphere were triethylamine (31 uL) and 4-trifluoromethoxyphenyl isocyanate (30 , uL, 0.145 MMOL) added. The reaction was stirred for three days. PS-Trisamine (0. 16 g, 3.58 mmol/g, 0.56 MMOL) was added and the reaction was stirrede for two more days. The resin was filtered off and the reaction mixture was concentrated in vacuo. The crude product was purified by acidic ion exchange chromatography (SCX-colon) giving 29 mg (59%) of the title product. LCMS (AN20P10) : RT = 5.52 min, (M-1) = 439.0 m/z.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; 7TM PHARMA A/S; LITTLE, Paul Brian; WO2004/48319; (2004); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Some common heterocyclic compound, 144-80-9, name is N-((4-Aminophenyl)sulfonyl)acetamide, molecular formula is C8H10N2O3S, 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. 144-80-9

General procedure: A mixture of appropriate sulfonamide 1 (10 mmol) in DMF (20 mL) and the appropriate isothiocyanate (10 mmol) in dioxin (20 mL) was heated on a water bath for 1 h, cooled and then poured onto ice cooled water. The pale yellow solid thus obtained was filtered and recrystallized from ethanol as needles.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 144-80-9, its application will become more common.

Reference:
Article; Faidallah, Hassan M.; Khan, Khalid A.; Journal of Fluorine Chemistry; vol. 142; (2012); p. 96 – 104;,
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1114-51-8, A common heterocyclic compound, 1114-51-8, name is N,N-Diethylpropionamide, molecular formula is C7H15NO, 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.

(1.43) from DAQ and N-diethylpropionamide the 2,6-bis-(diethylamino-1-propylene-imino)-anthraquinone having a melting point of 78 C.

The synthetic route of 1114-51-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hoechst Aktiengesellschaft; US4078086; (1978); A;,
Amide – Wikipedia,
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A common heterocyclic compound, 7341-96-0, name is Propiolamide, molecular formula is C3H3NO, 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. 7341-96-0.

General procedure: CuI (0.01mmol) was added to a mixture of isatin (1) (1.0 mmol), L-proline (2) (1.0 mmol) and alkyne (3)(1.0 mmol) in acetonitrile and the reaction mixture was stirred at 80 C for2-3 h under nitrogen. The solvent was then removed under reduced pressure andthe concentrated reaction mass was purified by column chromatography on silicagel using 50% hexane-ethyl acetate to afford the desired compound.. 2-oxo-5′,6′,7′,7a’-tetrahydrospiro[indoline-3,3′-pyrrolizine]-2′-carboxamide 4a) Off white solid; Yield: 92%; mp: 260-263 C; lHNMR (400 MHz, DMSO-d6): d 10.0 (s, 1H), 7.50 (s, 1H), 7.20-7.15 (m, 1H),7.00-6.70 (m, 5H), 4.45-4.35 (m, 1H), 2.50-2.40 (m, 2H), 2.05-1.95 (m, 1H),1.80-1.45 (m, 3H); 13C NMR (100 MHz, DMSO-d6): delta 178.5,163.8, 143.2, 139.1, 137.7, 128.8, 127.3, 125.4, 120.4, 109.4, 76.9, 71.6, 47.8,30.6, 26.8; IR (KBr): 3275, 2873, 1663, 1598, 1472, 1384, 1205, 745 cm-1;m/z (ES): 270.12 (M+1, 100 %); HRMS: m/z [M + H] calcd for C15H16N3O2:270.1243; found: 270.1240.

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

Reference:
Article; Singh, Shambhu Nath; Regati, Sridhar; Paul, Abir Kumar; Layek, Mohosin; Jayaprakash, Sarva; Reddy, K. Venkateshwara; Deora, Girdhar Singh; Mukherjee, Soumita; Pal, Manojit; Tetrahedron Letters; vol. 54; 40; (2013); p. 5448 – 5452;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding some certain compound to certain chemical reactions, such as: 3984-14-3, name is N,N-Dimethylsulfamide, 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 3984-14-3. 3984-14-3

Intermediate 3 1H-Indole-6-carboxamide, 2-bromo-3-cyclohexyl-N-[(dimethylamino)sulfonyl]-. 1,1′-Carbonyldiimidazole (1.17 g, 7.2 mmol) was added to a stirred solution of 2-bromo-3-cyclohexyl-1H-indole-6-carboxylic acid (2.03 g, 6.3 mmol) in THF (6 mL) at 22 C. The evolution of CO2 was instantaneous and when it slowed the solution was heated at 50 C. for 1 hr and then cooled to 22 C. N,N-Dimethylsulfamide (0.94 g, 7.56 mmol) was added followed by the dropwise addition of a solution of DBU (1.34 g ,8.8 mmol) in THF (4 mL). Stirring was continued for 24 hr. The mixture was partitioned between ethyl acetate and dilute HCl. The ethyl acetate layer was washed with water followed by brine and dried over Na2SO4. The extract was concentrated to dryness to leave the title product as a pale yellow friable foam, (2.0 g, 74%, >90% purity, estimated from NMR). 1H NMR (300 MHz, DMSO-D6) delta ppm 1.28-1.49 (m, 3 H) 1.59-2.04 (m, 7 H) 2.74-2.82 (m, 1 H) 2.88 (s, 6 H) 7.57 (dd, J=8.42, 1.46 Hz, 1 H) 7.74 (d, J=8.78 Hz, 1 H) 7.91 (s, 1 H) 11.71 (s, 1 H) 12.08 (s, 1 H).An alternative method for the preparation of 1H-indole-6-carboxamide, 2-bromo-3-cyclohexyl-N-[(dimethylamino)sulfonyl]- is described below.To a 1 L four necked round bottom flask equipped with a mechanical stirrer, a temperature controller, a N2 inlet, and a condenser, under N2, was added 2-bromo-3-cyclohexyl-1H-indole-6-carboxylic acid (102.0 g, 0.259 mol) and dry THF (300 mL). After stirring for 10 min, CDI (50.3 g, 0.31 mol) was added portion wise. The reaction mixture was then heated to 50 C. for 2 h. After cooling to 30 C., N,N-dimethylaminosulfonamide (41.7 g, 0.336 mol) was added in one portion followed by addition of DBU (54.1 mL, 0.362 mol) drop wise over a period of 1 h. The reaction mixture was then stirred at rt for 20 h. The solvent was removed in vacuo and the residue was partitioned between EtOAc and 1 N HCl (1:1, 2 L). The organic layer was separated and the aqueous layer was extracted with EtOAc (500 mL). The combined organic layers were washed with brine (1.5 L) and dried over MgSO4. The solution was filtered and concentrated in vacuo to give the crude product (111.0 g). The crude product was suspended in EtOAc (400 mL) at 60 C. To the suspension was added heptane (2 L) slowly. The resulting suspension was stirred and cooled to 0 C. It was then filtered. The filter cake was rinsed with small amount of heptane and house vacuum air dried for 2 days. The product was collected as a white solid (92.0 g, 83%). 1H NMR (MeOD, 300 MHz) delta 7.89 (s, H), 7.77 (d, J=8.4 Hz, 1H), 7.55 (dd, J=8.4 and 1.8 Hz, 1H), 3.01 (s, 6H), 2.73-2.95 (m, 1H), 1.81-2.05 (m, 8H), 1.39-1.50 (m, 2H); m/z 429 (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 N,N-Dimethylsulfamide.

Reference:
Patent; Bristol-Myers Squibb Company; US2008/227769; (2008); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

2675-89-0, 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. 2675-89-0, name is 2-Chloro-N,N-dimethylacetamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

[Example 9] [2-(Dimethylamino)-2-oxoethyl] (6-{(pyridin-2-ylsulfonyl)[4-(thiazol-2-yl)benzyl]-aminomethyl}pyridin-2-ylamino)acetate To 1 ml of an N,N-dimethylformamide solution containing 174 mg (0.351 mmol) of (6-{(pyridin-2-ylsulfonyl)[4-(thiazol-2-yl)benzyl]aminomethyl}pyridin-2-ylamino)acetic acid obtained by the same manner as in Reference example 3-(b) were added 97 mg (0.70 mmol) of potassium carbonate and 47 mul (0.46 mmol) of2-chloro-N,N-dimethylacetamide, and the mixture was stirred at room temperature for 4 hours. After completion of the reaction, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated sodium chloride solution, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was applied to silica gel column chromatography (eluent; ethyl acetate_methanol=9:1 (V/V)), and the fractions containing the objective material were concentrated under reduced pressure to obtain 203 mg of the title compound as white foam substantially quantitatively. Mass spectrum (FAB, m/z): 581 (M++1). 1H-NMR spectrum (DMSO-d6, delta ppm): 8.67 (ddd, J=4.7, 1.8, 0.9 Hz, 1H), 7.96 (ddd, J=7.7, 7.7, 1.8 Hz, 1H), 7.92 (d, J=3.2 Hz, 1H), 7.88-7.83 (m, 2H), 7.81 (ddd, J=7.8, 1.0, 0.9 Hz, 1H), 7.78 (d, J=3.2 Hz, 1H), 7.59 (ddd, J=7.7, 4.7, 1.0 Hz, 1H), 7.38-7.33 (m, 2H), 7.21 (dd, J=8.3, 7.1 Hz, 1H), 6.92 (t, J=6.0 Hz, 0.8H), 6.35 (d, J=8.3 Hz, 1H), 6.31 (d, J=7.1 Hz, 1H), 4.77 (s, 2H), 4.73 (s, 2H), 4.27 (s, 2H), 3.98 (d, J=6.0 Hz, 2H), 2.87 (s, 3H), 2.78 (s, 3H). Rf value: 0.20 (ethyl acetate_methanol=50:1).

The synthetic route of 2675-89-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Ube Industries, Ltd.; EP2476678; (2012); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

1882-71-9, name is 2-Amino-5-methoxybenzamide, 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. 1882-71-9

General procedure: A solution of anthranilamide (30 mmol) in 1N HCl (120 mL) was stirred at 0 C for 20 min. Then, sodium nitrite (60 mmol) dissolved in deionized water (100 mL) was added dropwise to the above solution for 40 min. After another 2 h of stirringat 0 C, 30% NaOH solution was added slowly to adjustp H value to 8.0. The reaction mixture was allowed to stir vigorously for 15 min. The precipitated product was filtered, washed with deionized water (200 mL), and dried to afford compounds 10 in yields of 40-92%.

Statistics shows that 1882-71-9 is playing an increasingly important role. we look forward to future research findings about 2-Amino-5-methoxybenzamide.

Reference:
Article; Chen, Xiulei; Zhou, Zhen; Li, Zhong; Xu, Xiaoyong; Phosphorus, Sulfur and Silicon and the Related Elements; (2019);,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics