Month: January 2021

Some common heterocyclic compound, 198211-38-0, name is tert-Butyl 3-azabicyclo[3.1.0]hexan-6-ylcarbamate, molecular formula is C10H18N2O2, 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. Safety of tert-Butyl 3-azabicyclo[3.1.0]hexan-6-ylcarbamate

General procedure: Intermediate C17.ii (130 mg) and K2C03 (69 mg) were suspended with DMF. 6-(Boc-amino)-3-azabicyclo[3. 1.0]hexane (81 mg; commercial) was added portionwise and themixture was stirred at rt for 1 day. The mixture was concentrated under reduced pressure and the residue was portioned between EA and water. The aq. layer was extracted with EA and the combined org. layers were washed with water and brine, dried over Mg504 and concentrated under reduced pressure. The title compound was obtained, after purificationby CC (Combiflash; Hept/EA 0:1 to 1:0), as a yellow oil (108 mg; 62% yield). M53 (ESI, mlz): 457.10 [M+H+]; tR = 0.73 mm.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 198211-38-0, its application will become more common.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; CREN, Sylvaine; FRIEDLI, Astrid; RUEEDI, Georg; ZUMBRUNN, Cornelia; (200 pag.)WO2016/59097; (2016); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 4424-80-0,Some common heterocyclic compound, 4424-80-0, name is 4,5-Dihydro-1H-benzo[b]azepin-2(3H)-one, molecular formula is C10H11NO, 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.

Step 1 Production of 2,3,4,5-tetrahydro-1H-benzo[b]azepine Lithium aluminum hydride (100 mg) was suspended in tetrahydrofuran (10 mL), 1,3,4,5-tetrahydrobenzo[b]azepin-2-one (245 mg) was added under ice-cooling by small portions. After heating under reflux for 5.5 hrs, water (0.1 mL), 15% aqueous sodium hydroxide (0.1 mL) and water (0.3 mL) were successively added under ice-cooling, and the mixture was stirred at room temperature. The mixture was dried over anhydrous sodium sulfate, and concentrated to give the title compound (301.6 mg) as a yellow oil.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4,5-Dihydro-1H-benzo[b]azepin-2(3H)-one, its application will become more common.

Reference:
Patent; Japan Tobacco Inc.; US2008/64871; (2008); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 16375-88-5,Some common heterocyclic compound, 16375-88-5, name is N-(4-(Hydroxymethyl)phenyl)acetamide, molecular formula is C9H11NO2, 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: Bismuth vanadate (32.3 mg, 100 mmol) was added to a Schlenkflask containing benzyl alcohol stock solution (1 mL, 0.1 mmol inacetonitrile) and acetonitrile (9 mL). The mixture was left to stirfor 30 min to disperse the catalyst under a dioxygen atmospherevia a balloon. The mixture was then irradiated with a 30W blueLED array at a distance of 2 cmwith an irradiance of 245mWcm2.The mixture reached ca. 40 C by the end of the reaction and afterirradiation, the catalyst was removed using centrifugation at4000 rpm for 30 min. For GC analysis, 1 mL of supernatant wastaken and 1 lL injected. For NMR analysis, the supernatant wasreduced in volume using a rotary evaporator at 65 mbar at 20 C,and the residue dissolved in d6-DMSO containing maleic acid asan internal standard.

The synthetic route of 16375-88-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Unsworth, Christopher A.; Coulson, Ben; Chechik, Victor; Douthwaite, Richard E.; Journal of Catalysis; vol. 354; (2017); p. 152 – 159;,
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. 2675-89-0, name is 2-Chloro-N,N-dimethylacetamide, A new synthetic method of this compound is introduced below., HPLC of Formula: C4H8ClNO

A solution of 4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-lH-pyrazole (0.8 g, 4.1 mmol), cesium carbonate (2.0 g, 6.2 mmol), and 2-chloro-N,N-dimethylacetamide (0.47 rnL, 4.5 mmol) in DMF (14 mL) was heated in a microwave at 900C for 1 hr. The crude reaction mixtures were then diluted with water (300 mL) and extracted with ethyl acetate (3 x 50 mL). Product was purified by silica gel column using DCM/EtOAc/MeOH (8/1.5/0.5) as eluent to provide N,N-dimethyl-2-(4-(4,4,5 ,5-tetramethyl- 1 ,3 ,2-dioxaborolan-2-yl)- 1 H-pyrazol- 1 – yl)acetamide (1.3 g) as a light yellow oil. ESI-MS:m/z 280.3 (M+H)+.

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; TAKEDA PHARMACEUTICAL COMPANY LIMITED; BRESSI, Jerome, C.; CHU, Shaosong; ERICKSON, Philip; KOMANDLA, Mallareddy; KWOK, Lily; LAWSON, John, D.; STAFFORD, Jeffrey, A.; WALLACE, Michael, B.; ZHANG, Zhiyuan; DAS, Sanjib; WO2010/19899; (2010); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Related Products of 6292-59-7, 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. 6292-59-7 name is 4-(tert-Butyl)benzenesulfonamide, 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: In air, a 10 mL of dried Schlenk tube was charged with azoxybenzene (1a; 79.2 mg, 0.40 mmol), TsNH2 (2a; 102.6 mg, 0.60 mmol), [Cp*Rh- Cl2]2 (3.1 mg, 0.005 mmol), AgSbF6 (13.7 mg, 0.04 mmol), and PhI(OAc)2 (193.2 mg, 0.60 mmol). Then the freshly distilled 1,2-dichloroethane (1.0 mL) was injected into the Schlenk tube. The reaction tube was placed in an oil bath and stirred at 80 ¡ãC for 16 h; then it was cooled to r.t. and the reaction completion was checked by TLC. H2O (10.0 mL) was subsequently added to the reaction mixture and extracted with CH2Cl2 (3 5.0 mL). The organic layers were combined, dried (MgSO4), and concentrated under reduced pressure to yield the crude product, which was further purified by flash chromatography (silica gel, PE/EtOAc 9:1 ? 5:1, v/v), affording the product 3a as a pale yellow solid (120.4 mg, 0.33 mmol, 82percent);

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

Reference:
Article; Li, Hongji; Deng, Hong; Synthesis; vol. 49; 12; (2017); p. 2711 – 2720;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 1129-26-6,Some common heterocyclic compound, 1129-26-6, name is 4-Methoxybenzenesulfonamide, molecular formula is C7H9NO3S, 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: N-acyl-indoline 1 (0.15mmol), amide 2 (0.3mmol), [RhCp*Cl2]2 (5mol%), AgOTf (20mol%), AgOAc (20mol%), PhI(OAc)2 (0.15mmol), HOAc(0.45mmol) and DCE (1.5 mL) were added into the tube and sealed. The reaction vessel was evacuated and back filled with N2 in three times. The reaction mixture was vigorously stirred at 100 C for 16 h. Then, the solvent was evaporated under reduced pressure and the residue was purified by flash column chromatography on silica gel to give the desired product.

The synthetic route of 1129-26-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Dong, Yaqun; Sun, Song; Yu, Jin-tao; Cheng, Jiang; Tetrahedron Letters; vol. 60; 20; (2019); p. 1349 – 1352;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 78191-00-1, name is N-Methoxy-N-methylacetamide, 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 78191-00-1, Product Details of 78191-00-1

a) To a solution of 1-octyne in tetrahydrofuran (THF, 180 mL) previously cooled to -78 C. is added under nitrogen n-buyllithium (2.5 M solution in hexane, 33.2 mL, 83 mmol). The colorless mixture is stirred 1 h and is then treated with N-methoxy-methylacetamide in THF (20 mL). The reaction mixture is stirred at room temperature for 4 h. After that time 3M HCl solution (100 mL) is added. Tert-butyl-methyl ether (TBME) is added and the reaction mixture is extracted with TBME (3¡Á100 mL). The combined organic layers are washed with saturated NaHCO3, dried over magnesium sulphate and the volatiles are removed on rotary evaporator. The residue is then purified by flash column chromatography (eluent: ethyl acetate/hexane 1:10) to obtain product 121 (colorless oil, 6.2 g, yield: 64%). (0445) NMR: 1H (400.1 MHz, CDCl3), delta=2.35 (2H, t, J=7.2 Hz), 2.31 (3H, s), 1.57 (2H, quint., J=7.2 Hz), 1.43-1.35 (2H, m), 1.33-1.25 (4H, m), 0.89 (3H, t, J=7.0 Hz); 13C (100.1 MHz, CDCl3), delta=184.9, 94.2, 81.4, 32.7, 31.2, 28.5, 27.6, 22.4, 18.9, 14.0.

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; BASF SE; Welker, Matthias; Turbiez, Mathieu G. R.; Chebotareva, Natalia; Kirner, Hans Juerg; (74 pag.)US9550791; (2017); B2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 5466-88-6, 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 5466-88-6 as follows.

General procedure: Phosphoric acid (3.15 g, 0.032 mol) and TFAA (21.8 mL, 0.104 mol) were added to the mixture of 4H-Benzo [1,4]oxazin-3-one (4 g, 0.026 mol) and substituted phenylacetic acid (1.1eq), at 0 C. After completion of addition, the mixture was allowed to warm to room temperature and stirred for 1 h. The reaction mixture was cooled to 0 C and adjusted the pH to 7 by adding the saturated NaHCO3 solution. The precipitated solid was filtered, washed with water and dried to give the desired product.

According to the analysis of related databases, 5466-88-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Rajitha, Chittipaka; Dubey; Sunku, Venkataiah; Javier Piedrafita; Veeramaneni, Venugopal Rao; Pal, Manojit; European Journal of Medicinal Chemistry; vol. 46; 10; (2011); p. 4887 – 4896;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 127828-22-2, 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. 127828-22-2, name is tert-Butyl (2-(2-aminoethoxy)ethyl)carbamate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A solution of 38.6 mg (0.23 mmol) of AgNO3 in 1 ml of dimethylformamide (DMF) was added portionwise over 1.5 h to a stirred solution of 78.2 mg (0.24 mmol) of 1 in 1.6 ml of DMF at room temperature in the dark. The mixture was stirred for 5 h in the dark, and the AgCl precipitate was then filtered off. The resulting pale-yellow DMF solution of [PtenCl(dmf)](NO3) was used as a starting material for the preparation of 1b and 1c as described below.A solution of 1a obtained as above was added to 40 mg (0.2 mmol) of NONBoc (2d) in the dark. The resulting solution was stirred overnight in the dark at room temperature. Then DMF was removed in vacuo. Excess of water was added to the residue, and a yellow precipitate of PtenCl2 was filtered off. The remaining filtrate of 1c was lyophilized. Yield: 87 mg. 195Pt NMR (H2O): delta -2645.

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, tert-Butyl (2-(2-aminoethoxy)ethyl)carbamate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Kreatech Biotechnology B.V.; EP1745802; (2007); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 915087-25-1, These common heterocyclic compound, 915087-25-1, name is 4-Amino-2-fluoro-N-methylbenzamide, 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.

A mixture of 4-amino-2-fluoro-N-methylbenzamide (2 g, 11.9 mmol), TMSCN (2.2 mL, 17.9 mmol), TMSOTf (0.1 mL, 0.6 mmol), and acetone (10 mL, 140 mmol) in DCM (20 mL) was stirred at room temperature overnight. The white solid was filtered, washed with a small amount of DCM, and dried to afford 1.12 g of 4-((2-cyanopropan-2-yl)amino)-2-fluoro- N-methylbenzamide as a white solid. lR NMR (300 MHz, DMSO-d6) delta 7.79 (t, 1H), 7.56 (t, 1H), 6.88 (s, 1H), 6.67 (dd, 1H), 6.54 (dd, 1H), 2.75 (d, 3H), 1.67 (s, 6H).

Statistics shows that 4-Amino-2-fluoro-N-methylbenzamide is playing an increasingly important role. we look forward to future research findings about 915087-25-1.

Reference:
Patent; ARAGON PHARMACEUTICALS, INC.; SMITH, Nicholas, D.; BONNEFOUS, Celine; JULIEN, Jackaline, D.; WO2011/103202; (2011); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics