Month: October 2020

A common heterocyclic compound, 239074-29-4, name is tert-Butyl (trans-4-(hydroxymethyl)cyclohexyl)carbamate, molecular formula is C12H23NO3, 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. 239074-29-4.

A suspension of 7-chloro-8-hydroxy-l-methyl-l,5-naphthyridin-2(lH)-one (1 g, 4.75 mmol) (for a synthesis see WO2008006648 Example l(c)) in THF (24 ml) was stirred at rt and treated with 1,1-dimethylethyl [trans-4-(hydroxymethyl)cyclohexyl]carbamate (1.089 g, 4.75 mmol, for a preparation see Example l(g)), triphenylphosphine (1.619 g, 6.17 mmol) and DIAD (1.215 ml, 6.17 mmol). The resulting yellow suspension was stirred for 30 min then heated at 8O0C for 3.5 hours. Additional triphenylphosphine (0.8 g, 3.05 mmol) and DIAD (0.6 ml, 3.05 mmol) were added and the suspension (now orange) was heated to 8O0C for 2 hours. The suspension was cooled and stirred at rt overnight. The solvent was evaporated under vacuum and to deliver an orange gum. Chromatography on silica, eluting with 0-50% DCM/CH3CN gave a white solid that contained residual triphenylphosphine oxide. Diethylether (50 mL) was added and the resulting suspension was stirred for 30 minutes, filtered under vacuum. The precipitate was dissolved in DCM, filtered and the filtrate was evaporated to give the title compound (1.16 g, 42%). MS (ES+) m/z 422 [MH+].

The synthetic route of tert-Butyl (trans-4-(hydroxymethyl)cyclohexyl)carbamate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; JONES, Graham, Elgin; MARKWELL, Roger, Edward; HENNESSY, Alan Joseph; MILES, Timothy; PEARSON, Neil David; WO2010/45987; (2010); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

354-38-1, A common compound: 354-38-1, name is 2,2,2-Trifluoroacetamide, belongs to amides-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

General procedure: The enynones (2) (0.50 mmol), trifluoroacetamide (1) (100 mg, 0.88 mmol), RuCl2(bpy)3 (9.6 mg, 0.015 mmol, 0.030 equiv), Na2CO3 (53 mg, 0.50 mmol, 1.0 equiv), and 1,2-dichloromethane (5.0 mL) were added to a reaction tube equipped with a stir bar. The tube was then exposed to blue LEDs irradiation at room temperature in air with stirring for 8 h. After the reaction was completed, the reaction mixture was extracted with 1,2-dichloromethane (30 mL),and washed with water (30 mL). The organic phase was dried with MgSO4 and evaporated in vacuo after filtration. The resulting residue was purified by column chromatography on silica gel to give the desired products 3.

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, 2,2,2-Trifluoroacetamide, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Chen, Taotao; Wu, Wei; Weng, Zhiqiang; Tetrahedron; vol. 75; 51; (2019);,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

16982-21-1, Adding a certain compound to certain chemical reactions, such as: 16982-21-1, name is Ethyl 2-amino-2-thioxoacetate, 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 16982-21-1.

(k) Ethyl 4-phenylthiazole-2-carboxylate[00397] To ethyl 2-amino-2-thioxoacetate (4 g, 30 mmol) in ethanol (50 mL) was added pyridine (0.24 g, 3 mmol). 2-Bromo-l-phenylethanone (5 g, 25 mmol) was added after 10 minutes and the mixture was then heated at reflux for 6 hours. The resulting mixture was washed with water and extracted with EtOAc and dried over anhydrous sodium sulfate. The solution was then concentrated under vacuum to give a crude product, which was purified by column chromatography to afford the title compound as a white solid (4.4 g). MS (ESI) m/z 233 (M+H+).

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, Ethyl 2-amino-2-thioxoacetate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SUNOVION PHARMACEUTICALS INC.; CAMPBELL, John, Emerson; HEWITT, Michael, Charles; JONES, Philip; XIE, Linghong; WO2011/150156; (2011); A2;,
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 65854-91-3 as follows. 65854-91-3

EXAMPLE 3 Preparation of 4-Chloro-2-trifluoroacetylaniline, hydrochloride hydrate. N-(4-Chlorophenyl)-2,2-dimethyl propanamide (36.7 kg, 173 mol) was charged to a solution of TMEDA (20.2 kg, 174 mol) in anhydrous t-butyl methyl ether (271.5 kg) and cooled to -20 C. To the cold slurry was added 2.7 N n-butyllithium in hexane (101.9 kg, 393 mol) while keeping the temperature below 5 C. After aging 2 hr at 0 to 5 C., the solution was cooled below -15 C. then rapidly reacted with ethyl trifluoroacetate (34.5 kg, 243 mol). After 30 min, the resulting solution was quenched into 3N HCl (196 L, 589 mol) keeping the temperature below 25 C. After removal of the aqueous phase, the organic solution was concentrated by distilling approximately 200 L of solvent. Acetic acid (352 kg) was added while distilling 325 kg solvent under 100 mm vacuum. After cooling the solution to 30 C., 12 N HCl (43.4 kg, 434 mol) was added and the mixture heated to 65 to 70 C. and held 4 hours. The resulting slurry was cooled to 5 C. and the product was collected by filtration, washed with ethyl acetate (50.5 kg) and dried in vacuo to give 42.1 kg (87%) of the title compound as a white crystalline solid: mp 159-162 dec; 1 H NMR (300 MHz, DMSO-d6) d 7.65-7.5 (complex, 2H), 7.1 (d, J=8 Hz, 1H), 7.0 (brs, 3H); 19 F NMR (282 MHz, DMSO-d6) delta-69.5.

According to the analysis of related databases, 65854-91-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; DuPont Pharmaceuticals Company; US6028237; (2000); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

112101-81-2, 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. 112101-81-2, name is R-5-(2-Aminopropyl)-2-methoxybenzenesulfonamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

The oily mass of formula-IIId obtained in step (i) (c) is taken and dissolved in 125.0ml of n-butanol. The solution is heated to 100C under nitrogen atmosphere. A solution of 29.1gms (0.1mole) of 2-(2-ethoxyphenoxy) ethyl iodide in 30ml of n-butanol is slowly added at 100-105C over a period of 3-4 hrs and maintained at 100-110C for further 4hrs. Then n-butanol is distilled off under vacuum at temp not exceeding 80C. The resulting mass is cooled to 20C and vacuum released under nitrogen atmosphere. 50.0ml of n-hexane is added to the mixture. An uniform slurry is made and the product is allowed to solidify at 0-5C. It is filtered and washed with 50ml of n-hexane. The product is dried at 40-50C under vacuum to obtain 22.0gms solid of quarternary ammonium salt of formula-IId. Recrystallized (from acetonitrile) has the following characteristics. MR : 200-208C 1H NMR : (200MHz, DMSO-d6) delta 1.15-1.19 (d, 3H), 1.28-1.31 (t, 3H), 2.60-2.70 (m, 2H), 3.40 (broad, 2H), 3.46-3.54 (m, 3H), 3.9 (s, 3H), 3.87-4.01 (dd, 4H), 4.20- 4.22 (t, 2H), 6.92-7.67 (aromatic, 11H), 8.15 (s, imine, 1H) IR : (KBr), 3305, 3210, 2930, 1632, 1609, 1494, 1439, 1330, 1282, 1252, 1456, 1075, 1011, 533, 522, 454 cm-1

The synthetic route of 112101-81-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NATCO PHARMA LIMITED; WO2004/16582; (2004); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

127828-22-2, A common compound: 127828-22-2, name is tert-Butyl (2-(2-aminoethoxy)ethyl)carbamate, belongs to amides-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

General procedure: To a solution of mono-Boc protected diamine linker (0.1 mmol, 1 eq) and Imatinib- COOH (54 mg, 0.1 mmol, 1 eq) in DMF (1 mL), COMU (43 mg, 0.1 mmol, 1 eq) and DIPEA (48 mircoL) were added. The reaction mixture was stirred at room temperature for 1 hour, then quenched with ice cold water. Volatiles were removed in vacuum and the crude mixture was purified by preparative HPLC (METHOD 2). Fractions containing the desired product were evaporated under reduced pressure and the reside was dissolved in DCM (1 mL) and treated with a solution of anhydrous HC1 in dioxane (4M, 1 mL). After 1 hour, volatiles were removed under reduced pressure and the reside was freeze dried in order to remove any excess of acid.L). After 1 hour, volatiles were removed under reduced pressure and the reside was freeze dried in order to remove any excess of acid. Analytical data (HRMS) are provided in table V.

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; UNIVERSITY OF DUNDEE; TESTA, Andrea; HUGHES, Scott; BUTCHER, Steven Peter; CIULLI, Alessio; (279 pag.)WO2019/238886; (2019); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

1118-92-9, The chemical industry reduces the impact on the environment during synthesis 1118-92-9, name is N,N-Dimethyloctanamide, I believe this compound will play a more active role in future production and life.

In a 10 mL single-mouth bottle, nitrogen protection, adding 0.50 mmol of compound 1i,2.5 mL of n-hexane, 350 g/L aqueous sodium chloride solution (H2O: 1.0 mmol), 2.0 mmol of sodium dispersion reagent (34.1% by weight, suspension of mineral oil,Particle size <100mum), stirred at 0 C for 180min, raised to room temperature,The reaction was quenched with saturated aqueous sodium bicarbonate.Adding ether and saturated brine to extract, the organic phase is dried,Concentrated, separated by column chromatography,Obtained 29.3 mg of the target compound 3i,The yield was 37% The chemical industry reduces the impact on the environment during synthesis N,N-Dimethyloctanamide. I believe this compound will play a more active role in future production and life. Reference:
Patent; China Agricultural University; An Jie; Li Hengchao; Zhang Bin; Yan Yuhao; Luo Shihui; Zhang Yuntong; (23 pag.)CN110054538; (2019); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

1118-69-0, name is N-Isopropylacetamide, 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. 1118-69-0

The compound of formula XIV-1 (31.05 g, 0.15 mol), the compound of formula XIII-1 (30.3 g, 0.30 mmol)Phosphorus oxychloride(20.9 mL, 0.225 mol) were added sequentially to anhydrous toluene. Triethylamine (31.3 mL, 0.225 mol) was added in an ice bathConstant pressure funnel slowly added dropwise to the reaction flask,Maintain the internal temperature is less than 60 .The reaction flask was transferred to an oil bath and heated to reflux.After 2 hours, the reaction flask was cooled to room temperature, slowly poured into 300 g of ice water mixture, 300 ml of ethyl acetate was added, sufficientAfter the mixture was separated, the aqueous layer was extracted with 200 ml of ethyl acetate again. The combined organic layers were washed with saturated brine and dried over anhydrous sulfuric acidSodium dried, concentrated under reduced pressure to give a pale yellow solid, beaten with 100 ml of petroleum ether for 10 minutes, filtered under reduced pressure to give a compound of formulaCompound XV-1 (28.0 g) as an off white solid (yield 92.3%)

Statistics shows that 1118-69-0 is playing an increasingly important role. we look forward to future research findings about N-Isopropylacetamide.

Reference:
Patent; Zhengda Tianqing Pharmaceutical Group Co., Ltd.; Zhang Yinsheng; Liu Yingshuai; Qin Hui; Li Yuan; Zhao Kaidi; Miao Lei; Hu Jie; Liu Haiyan; Wang Xiaojin; (33 pag.)CN107266421; (2017); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

These common heterocyclic compound, 5511-18-2, name is Adamantane-1-carboxamide, 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. 5511-18-2

Example 37 A solution of Example B13 (0.150 g, 0.837 mmol) in dioxane (10 mL) was treated with oxalyl chloride (0.150 g, 1.182 mmol), heated at 100 C. for 2 h, cooled to RT and concentrated to dryness. The residue was treated with a solution of Example A6 (0.150 g, 0.533 mmol) and pyridine (0.080 g, 1.011 mmol) in DCM (10 mL) and stirred at RT for 2 days. The mixture was concentrated to dryness, the residue treated with MeCN and the resulting solid collected via filtration and dried to afford N-((6-methyl-5-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)pyridin-2-yl)carbamoyl)adamantane-1-carboxamide (200 mg, 77%) as a white solid. 1H NMR (400 MHz, DMSO-d6): delta 11.18 (s, 1H), 10.32 (s, 1H), 8.35 (d, J=5.7 Hz, 1H), 8.24 (s, 1H), 7.95 (d, J=0.7 Hz, 1H), 7.90 (s, 1H), 7.61 (d, J=8.8 Hz, 1H), 7.16 (d, J=2.4 Hz, 1H), 6.60 (dd, J=5.7, 2.4 Hz, 1H), 3.83 (s, 3H), 2.25 (s, 3H), 1.98 (m, 3H), 1.89 (m, 6H), 1.66 (m, 6H); MS (ESI) m/z: 487.2 (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 5511-18-2.

Reference:
Patent; Deciphera Pharmaceuticals, LLC; Flynn, Daniel L.; Caldwell, Timothy Malcolm; Kaufman, Michael D.; Patt, William C.; Samarakoon, Thiwanka; Vogeti, Lakshminarayana; Yates, Karen M.; US2014/275080; (2014); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

404-24-0, 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. 404-24-0, name is 2,2,2-Trifluoro-N-phenylacetamide, This compound has unique chemical properties. The synthetic route is as follows.

A solution of 2-(2-aminobenzoyl)pyridine (1.29 g, 6.32 mmol, Syn. Comm. 1996, 26, 721-727) and trifluroacetic anhydride (1.10 mL, 7.79 mmol) in CHCl3 (35 mL) was heated at 42 C for 5 h. The reaction mixture was concentrated under reduced pressure and the residue was dissolved in EtOAc (ca. 250 mL), washed with saturated aqueous NaHCO3 (2 x 50 mL), H2O (1 x 50 mL), brine (1 x 50 mL), dried (Na2SO4) and concentrated under reduced pressure to give 1.91 g (99%) of the trifluoracetanilide. A mixture of KNO3 (905 mg, 8.96 mmol) in concentrated H2SO4 (12 mL) was added to a mixture of amide (1.76 g, 5.97 mmol) in concentrated H2SO4 (18mL) maintaining the reaction temperature at ? 16 C with an ice bath. The reaction mixture was allowed to warm to room temperature, stirred 4 h, and poured onto ice (ca. 150 g). The mixture was neutralized by slow addition of 25% aqueous NaOH (ca. 175 mL) maintaining the temperature at ? 18 C with an ice bath. The aqueous layer was extracted with EtOAc (2 x 200 mL). The combined organic extracts were washed with H2O (1 x 100 mL), brine (1 x 100 mL), dried (Na2SO4) and concentrated under reduced pressure to give a solid. Purification by flash chromatography, elution with 20% EtOAc-hexane, to provide 1.19 g (59%) of the 4-nitro-trifluoracetanilide compound as a yellow solid. A mixture of the nitro compound prepared as above (1.14 g, 3.36 mmol), MeOH (33 mL), and H2O (13mL) was treated with K2CO3 (2.32 g, 16.8 mmol) and heated at reflux for 2h. The reaction mixture was cooled to room temperature and MeOH was removed under reduced pressure. The aqueous residue was extracted with EtOAc (2 x 200 mL). The combined organic extracts were washed with H2O (1 x 100 mL), brine (1 x 100 mL), dried (Na2SO4) and concentrated under reduced pressure to give Int-4, in quantitative yield, as a yellow solid.

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; CeNes Limited; EP1183243; (2006); B1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics