Month: May 2021

Electric Literature of 58677-05-7,Some common heterocyclic compound, 58677-05-7, name is Ethyl 2-amino-5-methylbenzoate, molecular formula is C10H13NO2, 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: A solution ofethyl 2-nitrobenzoate (917 mg, 4.7 mmol) in MeOH (20 mL) and CH3COOH(0.1 mL) was subjected to two cycles N2/vacuum. Pd(OH)2/C10% wt (66 mg, 0.01 eq.) was added and the reaction mixture stirred at roomtemperature under H2 (1 atm) for 12 h. Propanal (337 muL, 4.7 mmol)and Pd(OH)2/C 10% wt (66 mg, 0.01 eq.) were added, and the reactionstirred at room temperature under H2 (1 atm) for additional 12 h.The suspension was filtered through Celite washing twice with CH2Cl2(20 mL). The solution recovered was evaporated under reduced pressure giving anoil after purification by flash chromatography (PE/AcOEt: 4/1). The oil obtained(1 eq.) was dissolved in dry CH2Cl2, and ethyl malonyl chloride(1 eq.) was added. The reaction mixture was stirred at room temperature under N2overnight. The reaction mixture was diluted with CH2Cl2and washed with a saturated solution of NaHCO3. Organic layers werethen washed with brine, dried over dry Na2SO4, filteredand evaporated under reduced pressure giving the expected compound after flashchromatography purification.

The synthetic route of 58677-05-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Manetti, Fabrizio; Petricci, Elena; Gabrielli, Annalisa; Mann, Andre; Faure, Helene; Gorojankina, Tatiana; Brasseur, Laurent; Hoch, Lucile; Ruat, Martial; Taddei, Maurizio; European Journal of Medicinal Chemistry; vol. 121; (2016); p. 747 – 757;,
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Some common heterocyclic compound, 42122-44-1, name is Methyl 3-(4-fluorophenyl)propiolate, molecular formula is C10H7FO2, 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. name: Methyl 3-(4-fluorophenyl)propiolate

To a solution ofN-(4-(benzyloxy)pyridin-3-yl)methanesulfonamide (9.0 g, 30.0mmol) in DCM (100 mL) was added (0-(mesitylsulfonyl)hydroxylamine) (20 g, 92 mmol) inDCM (20 mL) dropwise quickly at 0C under N2, and stirred for 2 hat room temperature. Afterconcentrated and the residue was dissolved in MeOH, and re-concentrated again. The residuewas dissolved in DMF (20 mL), and then added slowly dropwise to a mixture ofmethyl3-(4-15 fluorophenyl)propiolate (6 g, 34 mmol) and K2C03 (21 g, 154 mmol) in DMF (100 mL) at 0Cunder N2 . The mixture was stirred overnight at room temperature. The reaction mixture wasthen concentrated in vacuo and the resulting residue was suspended in H20 and extracted withDCM. The organic layer was washed with H20, brine and concentrated in vacuo. The residueobtained was purified using flash column chromatography on silica gel (eluted with PE I EtOAc20 from 5 I 1 to 3 I 1) to give methyl 5-(benzyloxy)-2-( 4-fluorophenyl)-6-(Nmethylmethylsulfonamido)pyrazolo[1,5-a]pyridine-3-carboxylate (3.5 g, yield: 24%). 1H-NMR(CDCh, 400 MHz) 8 8.54 (s, 1H), 7.70~7.74 (m, 2H), 7.68 (s, 1H), 7.42~7.44 (m, 5H), 7.13 (t, J= 8.8 Hz, 2H), 5.24 (s, 2H), 3.80 (s, 3H), 3.29 (s, 3H), 2.81 (s, 3H). MS (M+Ht: 484.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 42122-44-1, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; DAI, Xing; LIU, Hong; PALANI, Anandan; HE, Shuwen; BROCKUNIER, Linda L.; NARGUND, Ravi; MARCANTONIO, Karen; ZORN, Nicolas; XIAO, Dong; PENG, Xuanjia; LI, Peng; GUO, Tao; WO2014/121416; (2014); A1;,
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Adding a certain compound to certain chemical reactions, such as: 40876-98-0, name is Sodium 1,4-diethoxy-1,4-dioxobut-2-en-2-olate, belongs to esters-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 40876-98-0, Application In Synthesis of Sodium 1,4-diethoxy-1,4-dioxobut-2-en-2-olate

[4-((1R,5S,7S)-(1S,6R,8R)-9-bicyclo[4.3.1]dec-8-yl-3-oxa-9-aza-bicyclo[3.3.1]non-7-yl)-3-oxo-3,4-dihydro-quinoxalin-2-yl]-acetic acid ethyl ester (d6) To a solution of c1 (578 mg, 1.64 mmol) in ethanol (6 mL) was added oxalacetic acid diethyl ester sodium salt (977 mg, 4.41 mmol) and acetic acid (0.505 mL, 8.83 mmol) at temperature of about 25 C. under a nitrogen atmosphere. The mixture was stirred at 100 C. for 8 hr. The reaction mixture was diluted with saturated aqueous NaHCO3, then extracted with CHCl3 (2*30 mL). The combined organic phases were washed with saturated aqueous NaCl and dried (MgSO4) and concentrated. The resulting brown solid was chromatographed (silica-gel 45 g, AcOEt/n-hexane=1/3?1/0) to provide 385 mg of compound d6 as a light brown solid. (Yield 49%) d6: 1H-NMR (300 MHz, CDCl3) delta: 1.23-1.38 (m, 2H), 1.28 (t, J=7.2 Hz, 3H), 1.42-1.88 (m, 12H), 2.08-2.32 (m, 4H), 2.35-2.60 (m, 2H), 3.14 (m, 1H), 3.33 (d, J=10.8 Hz, 2H), 3.64 (d, J=10.8 Hz, 2H), 3.74-3.84 (m, 2H), 3.94 (s, 2H), 4.22 (q, J=7.2 Hz, 2H), 5.94 (m, 1H), 7.30 (t, J=7.8 Hz, 1H), 7.53 (td, J=1.2 Hz, 7.8 Hz, 1H), 7.83 (dd, J=1.2 Hz, 7.8 Hz, 1H), 8.18 (brs, 1H); LC/MS: m/z=494.3[M+H]+ (Calc: 493).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Sodium 1,4-diethoxy-1,4-dioxobut-2-en-2-olate, and friends who are interested can also refer to it.

Reference:
Patent; Shionogi & Co., Ltd.; Purdue Pharma L.P.; MARRA, Jeffrey Michael; Tsuno, Naoki; Ueno, Tatsuhiko; Zhou, Xiaoming; US2014/187544; (2014); A1;,
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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. 712317-32-3, name is 3-Azetidineacetic acid ethyl ester hydrochloride belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Quality Control of 3-Azetidineacetic acid ethyl ester hydrochloride

General procedure: Compound 8 (81 mg, 0.19 mmol) and ethyl 2-(4-piperidinyl)acetate (36 mg, 0.21 mmol) were dissolved in dichloromethane (3 ml). To the solution, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (44 mg, 0.23 mmol) and 1-hydroxybenzotriazole (9 mg, 0.06 mmol) were added, followed by stirring at room temperature for 3 h. The reaction mixture was diluted with chloroform and washed with satd NaHCO3 aq and brine. The organic layer was dried over Na2SO4, and then concentrated in vacuo. The residue was purified by preparative TLC (methanol-chloroform = 1:100) to give the title compound 9 (83 mg, 0.15 mmol, 77%).

The synthetic route of 712317-32-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ichikawa, Masanori; Ohtsuka, Masami; Ohki, Hitoshi; Haginoya, Noriyasu; Itoh, Masao; Sugita, Kazuyuki; Usui, Hiroyuki; Suzuki, Makoto; Terayama, Koji; Kanda, Akira; Bioorganic and Medicinal Chemistry; vol. 20; 9; (2012); p. 3072 – 3093;,
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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. 55150-07-7, name is Methyl 5-chloro-2-(methylamino)benzoate, A new synthetic method of this compound is introduced below., Recommanded Product: 55150-07-7

EXAMPLE 3 Under nitrogen, 3 g of a 55% strength dispersion of sodium hydride, which has been washed with pentane, are suspended in 30 ml of dimethylsulphoxide. After adding 9.3 g of methylphenylsulphone, the mixture is warmed to 60. After the evolution of hydrogen has ceased, the mixture is cooled to 0, diluted with 50 ml of tetrahydrofurane and, at this temperature, a solution of 4 g of methyl N-methyl-5-chloro-anthranilate in 20 ml of tetrahydrofurane is added dropwise in the course of about 20 minutes. The mixture is stirred overnight at room temperature and then poured into about 200 ml of ice-water. The resulting mixture is acidified with 2 N hydrochloric acid and stirred for a further 1 hour. The oily precipitate crystallises slowly. It is filtered off with suction and recrystallized from chloroform/ethanol. 2′-N-Methylamino-5′-chloro-2-(phenylsulphonyl)-acetophenone with a melting point of 160-162 is obtained.

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; Ciba-Geigy Corporation; US4192873; (1980); A;,
Ester – Wikipedia,
Ester – 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. 1150566-27-0, name is Ethyl 6-chloroimidazo[1,2-b]pyridazine-3-carboxylate, A new synthetic method of this compound is introduced below., Application In Synthesis of Ethyl 6-chloroimidazo[1,2-b]pyridazine-3-carboxylate

A 500 ml one-necked flask was charged with ethyl 6-chloroimidazo [1,2-b] pyridazine-3-carboxylate (11.28 g, 50 mmol)And methanol 50ml,Sodium hydroxide (4.0 g, 100 mmol)Dissolved in 100ml of water,Added to the reaction flask,The reaction was completed at 25 C for 4 hours. The reaction was completed by TLC and neutralized with 30% hydrochloric acid until pH = 4. The mixture was suction filtered, the filter cake was washed with a small amount of water,Dry to give 6-chloroimidazo [1,2-b] pyridazine-3-carboxylic acid purity, yield 91%.

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; Shandong Youbang Biochemical Technology Co., Ltd.; Tan Pingzhong; Geng Xuanping; Cheng Wei; Lai Xinsheng; Lai Chao; Lai Ziteng; (7 pag.)CN106831782; (2017); A;,
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Related Products of 27492-84-8,Some common heterocyclic compound, 27492-84-8, name is Methyl 4-amino-2-methoxybenzoate, molecular formula is C9H11NO3, 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.

Methyl 2-methoxy-4-aminobenzoate (10g, 55.25mmol) and hydroxylamine hydrochloride (15.36g, 221mmol) were taken up in MeOH (80ml) and a solution of KOH (15.4g, 275mmol) in MeOH (55ml) was added carefully. The resultant mixture was stirred at reflux for 36hrs. The volatiles were removed in vacuo. The residue was taken up in 1 M NaOH (50ml) and washed with ethyl acetate (EtOAc, 50ml). Concentrated HCl was added slowly until precipitation of a solid (pH was 10). The solid was filtered off, washed with H2O, then methyl-tert-butyl ether (MTBE) and dried under vacuum. 1H NMR showed the solid contained approx. 1/3 molar equivalent of ethyl acetate. The solid was taken up in 1M NaOH (100ml) and the EtOAc was removed in vacuo. Concentrated HCl was added carefully until precipitation of a solid (pH was 8). The solid was collected by filtration, washed with H2O, then MTBE and dried under vacuum to give 4.67g (47%) of the title compound as a dark red solid.1H NMR (delta, 250MHz, d6-DMSO): 3.75 (s, 3-H, OMe), 5.64 (s, 2-H, NH2), 6.14 (dd, 1-H, aromatic), 6.18 (brs, 1-H, aromatic), 7.48 (d, 1-H, aromatic), 8.73 (s, 1-H, NH), 10.06 (s, 1-H, OH).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 4-amino-2-methoxybenzoate, its application will become more common.

Reference:
Patent; Nogra Pharma Limited; NACCARI, Giancarlo; BARONI, Sergio; EP1910275; (2013); B1;,
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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. 6642-30-4, name is Methyl methylcarbamate, This compound has unique chemical properties. The synthetic route is as follows., Formula: C3H7NO2

EXAMPLE 10 2-SEC BUTYLPHENYL N-METHYLCARBAMATE To a mixture of methyl N-methylcarbamate (0.89 g, 0.01 mole) and 2-sec butylphenol (1.5 g, 0.01 mole) in dichloroethane (10 ml), a solution of phosphorus tribromide (2.7 g, 0.01 mole) in dichloro-ethane (6 ml) was added and the mixture was refluxed for eight hours. It was then worked up and purified as described earlier to give 2-sec butylphenyl N-methylcarbamate.

According to the analysis of related databases, 6642-30-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Council of Scientific and, Industrial Research; EP446514; (1991); A1;,
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Adding a certain compound to certain chemical reactions, such as: 41841-16-1, name is Methyl 2-(4-bromophenyl)acetate, belongs to esters-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 41841-16-1, Product Details of 41841-16-1

At 40 C., a solution of intermediate B.i (52 g) in THF (100 mL) was carefully added over a period of 40 min to a suspension of NaH (15.6 g) in dry THF (450 mL). Stirring was continued for 70 min without heating and the temperature dropped to 27 C. The evolution of gas stopped before dimethylcarbonate (76.42 mL) was added dropwise while the temperature of the mixture was maintained at 29-31 C. Stirring was continued for 22 h at rt. The mixture was cooled to -10 C. and then carefully neutralized to pH 6-7 with aq. HCl before bulk of the THF was removed in vacuo. The residue was dissolved in EA (700 mL), washed 3 times with 1 N aq. HCl-solution and once with brine, dried over MgSO4. Most of the EA was evaporated before Hex was added. The product crystallised overnight at 4 C. The crystals were collected, washed with Hex and dried to give the expected product as pale yellow crystals (45.9 g).1H-NMR (D6-DMSO): delta 3.66 (s, 6H); 5.07 (s, 1H); 7.30-7.34 (m, 2H); 7.55-7.59 (m, 2H),

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; Bolli, Martin; Boss, Christoph; Treiber, Alexander; US2012/142716; (2012); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 79669-50-4, name is methyl 5-bromo-2-methyl-benzoate, belongs to esters-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 79669-50-4, Recommanded Product: methyl 5-bromo-2-methyl-benzoate

5-Bromo-2-methylphenyl)methanolTo a solution of methyl 5-bromo-2-methylbenzoate (108 g, 471 mmol) in THF (1600 mL) was added LiAIH4(21.47 g, 566 mmol) slowly under nitrogen at 0 C. The resulting mixture was stirred at 0 C for 1 hr. Then 3.73 mL of water was added to the reaction mixture, followed by 3.75 mL of 10% NaOH, and 1 1.19 mL of water, filtered and concentrated to afford the title compound (5-bromo-2-methylphenyl)methanol (88 g, 416 mmol, 88 % yield). LC-MS MS m/z 185.1 (M-OH)+, 1.59 (ret. time)

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, methyl 5-bromo-2-methyl-benzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; ASTEX THERAPEUTICS LIMITED; BOEHM, Jeffrey Charles; DAVIES, Thomas Glanmor; WOOLFORD, Alison Jo-anne; GRIFFITHS-JONES, Charlotte Mary; WILLEMS, Hendrika Maria Gerarda; NORTON, David; SAXTY, Gordon; HEIGHTMAN, Thomas Daniel; LI, Tindy; KERNS, Jeffrey K.; DAVIS, Roderick S.; YAN, Hongxing; WO2015/92713; (2015); A1;,
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