Month: August 2021

Adding a certain compound to certain chemical reactions, such as: 618-48-4, name is 3-Chlorobenzamide, 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 618-48-4, SDS of cas: 618-48-4

General procedure: DDQ (20 mol%, 9.08 mg, 0.04 mmol) and BPO (20 mol%,9.69 mg, 0.04 mmol) were added to a mixture of 1,3-diarylpropene1 (0.24 mmol) and substrate 2 (0.2 mmol) in CH3NO2 (1 mL). Thereaction was carried out at 100 C under an oxygen atmosphere(oxygen balloon) for 24 h. The resulting mixture was purified by flashcolumn chromatography on silica gel (petroleum ether:ethyl acetate =10:1-20:1) to give the desired pure product 3a-k.

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:
Article; Cheng, Dongping; Zhou, Xiayi; Yuan, Kun; Yan, Jizhong; Journal of Chemical Research; vol. 40; 3; (2016); p. 127 – 129;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 50667-69-1, These common heterocyclic compound, 50667-69-1, name is 2,2,2-Trifluoro-N-(hydroxymethyl)acetamide, 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 solution of 2,3,4,5-tetrachloro-6-(2-(4′-carboxyphenyl)-7-chloro-6-hydroxy-3-oxo-3H-xanthen-9-yl)-benzoic acid (200 mg, 0.32 mmol, as prepared in Example 1), and N-(hydroxymethyl) trifluoroacetamide (44 mg, 0.31 mmol, Lancaster, Inc) in sulfuric acid (3 mL) was stirred at room temperature over a period of 16 h then poured into crushed ice (25 g). The crude product was extracted with EtOAc (250 mL) and the combined organic portions were washed with water (150 mL) and saturated NaCl (150 mL), dried (MgSO4) and concentrated. Purification via column chromatography (silica gel, 60 g, 1/1 EtOAc/hexanes 1% AcOH) gave the title compounds as a mixture (105 mg, 62%).

The synthetic route of 50667-69-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; O’Neill, Roger; Fisher, Peter V.; US2004/73014; (2004); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

316146-27-7, name is N-(4-Bromophenyl)-3-phenylpropanamide, 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. Computed Properties of C15H14BrNO

Intermediate 2 The reaction was carried out twice . POCI3 (1.225 mol) was added dropwise at 10 0C to DMF (0.525 mol) . Then intermediate 1 (0.175 mol) was added at room temperature. The mixture was stirred overnight at 80 0C, poured out on ice and extracted with CH2CI2 . The organic layer was dried (MgSO/t), filtered, and the solvent was evaporated, yielding 77.62 g (67percent) of intermediate 2. The product was used without further purification.

The synthetic route of 316146-27-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA N.V.; WO2007/14934; (2007); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Some common heterocyclic compound, 917342-29-1, name is tert-Butyl (trans-4-(2-hydroxyethyl)cyclohexyl)carbamate, molecular formula is C13H25NO3, 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. Recommanded Product: tert-Butyl (trans-4-(2-hydroxyethyl)cyclohexyl)carbamate

The compound 20 (3.40 g, 13.97 mmol) was dissolved in dichloromethane (34 mL). To the solution was added 4 mol/L hydrochloric acid (dioxane solution, 34.9 mL, 140 mmol). The mixture was stirred at room temperature for 3 hours. To the mixture, methanol (5 mL) was added and the mixture was stirred at room temperature for 1 hour. The solvent was evaporated under reduced pressure to give a compound 21 as a crude product.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 917342-29-1, its application will become more common.

Reference:
Patent; Shionogi & Co., Ltd.; TOBINAGA, Hiroyuki; MASUDA, Koji; KASUYA, Satoshi; INAGAKI, Masanao; YONEHARA, Mitsuhiro; MASUDA, Manami; (289 pag.)US2019/161501; (2019); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 71999-74-1, 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. 71999-74-1, name is N-Boc-2-chloroethylamine belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 142 Synthesis of the compound of the following formula (E-51) which has a substituent(s) of Example 142 of Table 23: N-(2,6-dichlorobenzoyl)-4-[6-(2-dimethylaminoethoxy)-1-methyl-2,4-quinazol ine-dione-3-yl]-L-phenylalanine t-Butyl 2-chloroethylcarbamate (157 mg), DMF (3 mL) and potassium carbonate (1384 mg) were added to the compound of Example 154 (450 mg) and stirred at 90 C. overnight. The mixture was extracted with ethyl acetate and treated in accordance with the ordinary method. The obtained crude material was dissolved in 4N hydrogen chloride dioxane solution (2 mL) and stirred at room temperature for 2 hours. After removing the solvent, the residue was purified with high performance liquid chromatography (water/acetonitrile, each containing 0.1% TFA) to obtain 350 mg of a purified material. Acetonitrile (5 mL), formalin (37 muL), acetic acid (26 muL) and triacetoxy sodium boron (98 mg) were added to the obtained purified material (170 mg) and stirred at room temperature for 2 hours. After removing the solvent, the residue was purified with high performance liquid chromatography (water/acetonitrile, each containing 0.1% TFA) to obtain 150 mg of a purified material. 4N hydrogen chloride dioxane solution (1 mL) and water (200 muL) were added to the obtained purified material (20 mg) and stirred at 90 C. for 2 hours. After removing the solvent, the residue was purified with high performance liquid chromatography (water/acetonitrile, each containing 0.1% TFA) to obtain 11 mg of a purified material. MS(ESI MH+): 599 Example 155 Synthesis of the Compound of the Following Formula (E-51) which has a Substituent(s) of Example 155 of Table 25: N-(2,6-dichlorobenzoyl)-4-[6-(2-dimethylaminoethoxy)-1-methyl-2,4-quinazol ine-dione-3-yl]-L-phenylalanine isopropylester t-Butyl 2-chloroethylcarbamate (157 mg), DMF (3 mL) and potassium carbonate (1384 mg) were added to the compound of Example 154 (450 mg) and stirred at 90 C. overnight. The mixture was extracted with ethyl acetate and treated in accordance with the ordinary method. The obtained crude material was dissolved in 4N hydrogen chloride dioxane solution (2 mL) and stirred at room temperature for 2 hours. After removing the solvent, the residue was purified with high performance liquid chromatography (water/acetonitrile, each containing 0.1% TFA) to obtain 350 mg of a purified material. Acetonitrile (5 mL), formalin (37 muL), acetic acid (26 muL) and triacetoxy sodium boron (98 mg) were added to the obtained purified material (170 mg) and stirred at room temperature for 2 hours. After removing the solvent, the residue was purified with high performance liquid chromatography (water/acetonitrile, each containing 0.1% TFA) to obtain 150 mg of the intended compound. MS(ESI MH+): 641

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, N-Boc-2-chloroethylamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Ajinomoto Co., Inc.; US2005/222141; (2005); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 96-30-0,Some common heterocyclic compound, 96-30-0, name is 2-Chloro-N-methylacetamide, molecular formula is C3H6ClNO, 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 3. Preparation of 2-[4-(5-cyano-2-methoxyphenoxy)piperidin-l-yl]-JV- methylacetamide (Compound (V)).; Compound (VI) (28.36 g, 95.82 mmoles), 2-chloro-N- methylacetamide (12.37 g, 114.98 mmoles) and potassium carbonate (33.11 g, 239.55 mmoles) were suspended in acetonitrile (161.36 g). The reaction mixture was heated at reflux for 3 hours. The reaction mixture was cooled to 200C and water (386.26 g) was charged. The reaction was heated to 75C and the volume reduced by distillation. Upon cooling crystallisation occurred. The resulting solid was isolated by filtration, washed twice with water (77.25 g and 128.75 g) and then dried to give compound (V) (27.95 g, 94% yield); 1H NMR (400 MHz, DMSO-J6) delta ppm 1.68 (m, 2 H) 1.91 (m, 2 H) 2.29 (m, 2 H) 2.61 (d, J=4.7 Hz, 3 H) 2.67 (m, 2 H) 2.88 (s, 2 H) 3.83 (s, 3 H) 4.41 (tt, J=8.3, 4.0 Hz, 1 H) 7.11 (d, J=8.4 Hz, 1 H) 7.40 (dd, J=8.4, 1.9 Hz, 1 H) 7.47 (d, J=I.9 Hz, 1 H) 7.68 (q, J=4.7 Hz, 1 H); Mass Spectrum: m/z (M + H)+ 304.2.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Chloro-N-methylacetamide, its application will become more common.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; BOARDMAN, Kay, Alison; CUNNINGHAM, Oliver, Robert; GOUNDRY, William; LAFFAN, David, Dermot, Patrick; WO2010/122340; (2010); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Some common heterocyclic compound, 143557-91-9, name is tert-Butyl 3-endo-3-hydroxy-8-azabicyclo[3.2.1]octane-8-carboxylate, molecular formula is C12H21NO3, 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. HPLC of Formula: C12H21NO3

Compound I (4.23 g) was dissolved in DMF (100 mL), and thereto were added benzyl bromide (3.32 mL) and sodium hydride (1.62 g), and the mixture was stirred at room temperature overnight. To the reaction mixture was added water, and the mixture was extracted with diisopropylether. The organic layer was dried over sodium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=3/1) to give the title compound II (4.98 g).1H-NMR (CDCl3) delta1.47 (s, 9H), 1.93-2.05 (m, 6H), 2.13-2.19 (m, 2H), 3.72 (m, 1H), 4.12-4.26 (m, 2H), 4.49-4.50 (m, 2H), 7.26-7.30 (m, 1H), 7.32-7.41 (m, 4H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 143557-91-9, its application will become more common.

Reference:
Patent; DAINIPPON SUMITOMO PHARMA CO., LTD.; US2012/225876; (2012); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 83922-54-7, 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. 83922-54-7 name is 4-(Methylsulfonamido)benzaldehyde, 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.

Step 1) diethyl (hydroxy (4- (methylsulfonamido) phenyl) methyl) phosphonate To a mixture of N- (4-formylphenyl) methanesulfonamide (2 g, 10 mmol) and diethyl phosphate (1.4 g, 10 mmol) was added a solution of sodium methoxide in methanol (0.5 mL, 0.25 mmol) . The mixture was stirred at rt for 12 hours. The reaction mixture was diluted with dichloromethane (20 mL) and washed with saturated aqueous NH4Cl (10 mL) , and dried over anhydrous Na2SO4and concentrated in vacuo. The residue was purified by silica gel column chromatography eluted with PE : EtOAc (V : V) 10 : 1 to give diethyl (hydroxy (4- (methylsulfonamido) phenyl) methyl) phosphonate as gray oil (2.9 g, 87) .[1120]MS (ESI, pos. ion) m/z: 338.3 [M+H]+.

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

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; ZHANG, Yingjun; XIE, Hongming; WU, Xiwei; REN, Qingyun; ZHANG, Jiancun; (236 pag.)WO2015/197028; (2015); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 17193-28-1, name is 1-Amino-1-cyclopentanecarboxamide, 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 17193-28-1, Safety of 1-Amino-1-cyclopentanecarboxamide

General procedure: 1-amino-cyclopentanecarboxamide (3) (8.0 g, 62.5 mmol) was acylated with alkyl acyl chloride (93.7 mmol) and triethylamine (17.3 mL, 125.0 mmol) in 50 mL dichloromethane(DCM) at 0 C.After the reaction was completed, the resulting mixture was addedwith 30 mLwater, and extracted with DCM (25 mL 3). The organiclayer was dried over MgSO4. After filtration, the solvent wasremoved under reduced pressure. The residue was dissolved in50 mL MeOH and then 50 mL 10 M KOH was added slowly. Themixturewas refluxed for 3 h. After cooled to room temperature, themixture was added 50 mL H2O and extracted with DCM(30 mL 4). The organic layer was dried over MgSO4, the solventwas removed under reduced pressure. The resulting residue waspurified by CC to give 5a-d.

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

Reference:
Article; Bao, Xiaolu; Zhu, Weibo; Yuan, Weidong; Zhu, Xingbo; Yan, Yijia; Tang, Hesheng; Chen, Zhilong; European Journal of Medicinal Chemistry; vol. 123; (2016); p. 115 – 127;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 53844-02-3, name is Benzyl (2-bromoethyl)carbamate, 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 53844-02-3, HPLC of Formula: C10H12BrNO2

1.7 g of 5-hydroxy-2-nitrophenyl ethanol and 4.3 g of potassium carbonate were dispersed in 20 ml N, N’- dimethyl formamide, and heated to 60 deg.] C for 1 hour. It was slowly added dropwise 2.82 g N- benzyloxycarbonyl-BrEA in methylene chloride (5 ml), 60 reaction for 24 hours. After completion of the reaction, the solvent was removed under reduced pressure, the product was dissolved in ethyl acetate, washed with saturated sodium bicarbonate solution, and saturated sodium chloride solution each, washed twice with distilled water wash, the organic phase was dried over anhydrous magnesium sulfate and 8 hours, filtered after concentration under reduced pressure, ethyl acetate / cyclohexane recrystallized twice to give product A.Take 1.56 g of product A was dissolved in 50 ml of anhydrous dichloromethane, was added under ice-cooling 1.25 g N- benzyloxycarbonyl-methionine, 1.33 g N, N’- dicyclohexyl carbodiimide and 0.2 g 4 – dimethylaminopyridine, stirred at room temperature overnight. After completion of the reaction, diluted hydrochloric acid with ice, saturated sodium bicarbonate solution and saturated sodium chloride solution each, washed twice with distilled water wash, dried over anhydrous sodium sulfate overnight. Suction filtered and the solvent was removed under reduced pressure, recrystallized twice from ethyl acetate. The obtained crystals were dissolved in 20 ml of chloroform, 20 ml of hydrogen chloride in ethyl acetate under ice-cooling a saturated solution, after 6 hours at room temperature the reaction dried under reduced pressure to give the productB. The product B was dissolved 0.687 g of methylene chloride and 50 ml of a mixed solvent of 8 ml of pyridine, cooled to -18 deg.] C, was added dropwise 10 ml of a toluene solution of phosgene (1.93 mol per liter) for 6 hours. The reaction mixture was washed with dilute hydrochloric acid each and twice with saturated sodium bicarbonate solution, saturated sodium chloride solution and distilled water for each wash. The organic phase was dried overnight over anhydrous magnesium sulfate, concentrated under reduced pressure after filtration

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Benzyl (2-bromoethyl)carbamate, and friends who are interested can also refer to it.

Reference:
Patent; Sichuan University; Ding, Mingming; Wang, Rui; Wu, Qiang; Tan, Hong; Zhang, Qin; Li, Jiehua; (14 pag.)CN105601550; (2016); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics