Month: March 2021

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. 88612-71-9, name is Ethyl 4-oxo-4H-quinolizine-3-carboxylate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Quality Control of Ethyl 4-oxo-4H-quinolizine-3-carboxylate

EXAMPLE 1 To a solution of 3-ethoxycarbonyl-4H-quinolizin-4-one (2.17 g) in methanol (65.2 ml) was added dropwise 6 N aqueous sodium hydroxide (6.5 ml) at room temperature. After stirring for 20 minutes, water (10 ml) was added. After stirring for 20 minutes, water (30 ml) was also added. After stirring for an hour, the reaction mixture was acidified to pH 3 with 4N aqueous hydrochloric acid. The precipitate was filtered and washed with water to give 4H-quinolizin-4-one-3-carboxylic acid (1.75 g) as pale yellow crystal. mp 233 C. IR (Nujol): 1730, 1610, 1585, 1320 cm-1 NMR (DMSO-d6) delta: 7.26 (d, 1H, J=9 Hz), 7.50-7.95 (m, 1H), 8.00-8.20 (m, 2H), 8.41 (d, 1H, J=9 Hz), 9.20-9.40 (m, 1H)

The synthetic route of 88612-71-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Fujisawa Pharmaceutical Co., Ltd.; US4698349; (1987); A;,
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These common heterocyclic compound, 4093-29-2, name is Methyl 4-acetamido-2-methoxybenzoate, 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. Safety of Methyl 4-acetamido-2-methoxybenzoate

At room temperature,Compound 64A (2.2 g, 10.0 mmol)Suspended in three volts of acetic anhydride, stirred until fully cooled to -10 C,Concentrated nitric acid (4 mL, 50 mmol) was slowly added dropwise at this temperature.After the dropwise addition, the temperature was raised to room temperature, and stirring was continued for 3 hours, and then the reaction liquid was poured into ice water.Extract with ethyl acetate (100 mL ¡Á 3), combine the organic phases, and dry.Concentration under reduced pressure gave compound 64B (2.8 g, 67%).

The synthetic route of Methyl 4-acetamido-2-methoxybenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Jiangsu Xiansheng Pharmaceutical Co., Ltd.; Chen Huanming; Liang Bo; Cao Wenjie; Zhang Guiping; Zhao Zhongqiang; Jiang Zhaojian; Zuo Gaolei; Xu Wanmei; Gong Hongju; Zhang Peng; Wang Jianghuai; Li Qingsong; Gao Chunhua; (79 pag.)CN104045552; (2019); B;,
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Reference of 72505-21-6,Some common heterocyclic compound, 72505-21-6, name is 4-(Trifluoromethyl)thiobenzamide, molecular formula is C8H6F3NS, 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.

5.0 g of Methyl 3-oxoheptanoate were dissolved in 80 ml dry dichloromethane. 2.82 ml Sulfurylchloride was added and the reaction mixture was stirred at room temperature for thirty minutes. Water was added and the mixture was extracted five times with dichloromethane (30 ml). The combined organic extracts were washed with water and brine and dried over MgSO4. The solvent was evaporated in vacuo to obtain 6.0 g 2-Chloro-3-oxo-heptanoic acid methyl ester as crude material. 6.0g 2-Chloro-3-oxo-heptanoic acid methyl ester was dissolved in 50 ml ethanol and 6.4 g 4-(Trifluoromethyl)thiobenzamide was added. The mixture was heated under reflux overnight. The cooled reaction mixture was evaporated in vacuo and column chromatography (n-heptane:ethyl acetate = 100:1 => 60:1) of the residue gave 7.4 g 4-Butyl-2-(4-trifluoromethyl-phenyl)-thiazole-5-carboxylic acid methyl ester as yellow oil. C16H16F3NO2S (343.37), MS(ESI): 344.1 (M+H+), Rf(n-heptane:ethyl acetate = 4:1) = 0.62.

The synthetic route of 72505-21-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Aventis Pharma Deutschland GmbH; EP1586573; (2005); A1;,
Amide – Wikipedia,
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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 39549-79-6 as follows. Recommanded Product: 2-Amino-4-methylbenzamide

General procedure: A 12mL vial was charged with MCM-41-2P-Pd(OAc)2 (2molpercent), 2-aminobenzamide (1mmol), aryl iodide (1mmol) (if solid) and a stirring bar. Then, DMF (2mL), aryl iodide (1mmol) (if liquid) and DBU (2mmol) were injected by syringe under an argon atmosphere. The vial was placed in an alloy plate, which was transferred into a 300mL Parr Instruments 4560 series autoclave under an argon atmosphere. After flushing the autoclave three times with CO, a pressure of 10bar CO was fixed at ambient temperature. The autoclave was heated for 20hat 120¡ãC. After completion of the reaction, the autoclave was cooled to room temperature and the pressure was released carefully. The reaction mixture was diluted with ethyl acetate (10mL) and filtered. The palladium catalyst was washed with distilled water (2¡Á5mL) and acetone (2¡Á5mL), and reused in the next run. The filtrate was concentrated in vacuo and the pure product was isolated by either washed with water, ethyl acetate and finally hexane or recrystallization from MeOH.

According to the analysis of related databases, 39549-79-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; You, Shengyong; Huang, Bin; Yan, Tao; Cai, Mingzhong; Journal of Organometallic Chemistry; vol. 875; (2018); p. 35 – 45;,
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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. 15910-91-5, name is 1-Methylcyclopropanecarboxamide, A new synthetic method of this compound is introduced below., category: amides-buliding-blocks

A -78 C. solution of 1-methylcyclopropanecarboxamide (1.35 g, 13.6 mmol) in THF (30 mL) was treated drop-wise with lithium bis(trimethylsilyl)amide (1M THF, 17.7 mL, 17.7 mmol), stirred for 0.5 h, treated drop-wise with a solution of isopropenyl chloroformate (1.94 mL, 17.7 mmol) in THF (5 mL), stirred at -78 C. for 1 h, then allowed to warm to RT and stirred for 1 h. The mixture was quenched with satd. NaHCO3, extracted with EtOAc (3*) and the combined organics were dried over Na2SO4 and concentrated to dryness to afford crude prop-1-en-2-yl (1-methylcyclopropanecarbonyl)carbamate (2.9 g, 116%) which was used without further purification.

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; Deciphera Pharmaceuticals, LLC; Flynn, Daniel L.; Caldwell, Timothy Malcolm; Samarakoon, Thiwanka; Vogeti, Lakshminarayana; Kaufman, Michael D.; Patt, William C.; Ahn, YuMi; US2014/275016; (2014); A1;,
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Synthetic Route of 6529-94-8, A common heterocyclic compound, 6529-94-8, name is 7-Methoxy-2H-benzo[b][1,4]oxazin-3(4H)-one, molecular formula is C9H9NO3, 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.

To a solution of 7-mthoxy-4H-benzo[1,4]oxazin-3-one (1.9 g, 10.6 mmol) in AcOH (20 ml_), is added droppedwise fuming HN03 (13.7 ml_) below 10 C. After stirred for 3 h, the reaction mixture is poured into ice cold water and the resulting white solids are collected by filtration. The solids are washed with H20 and hexane and dried in vacuo to give 7-mthoxy-6-nitro-4H-benzo[1,4]oxazin-3-one (1.4 g, 59%)

The synthetic route of 6529-94-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GmbH; WO2006/21454; (2006); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 478837-18-2, name is tert-Butyl 3-hydroxy-8-azabicyclo[3.2.1]octane-8-carboxylate, 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 478837-18-2, HPLC of Formula: C12H21NO3

tert-Butyl 3-hydroxy-8-azabicyclo[3.2.1 ]octane-8-carboxylate as obtained in step 1 (100 mg, 2.0 mmol), acetonitrile (2 mL) and 4 M hydrogen chloride in 1,4-dioxane (2 mL) were combined and stirred at 700C for 15 minutes. The reaction mixture was concentrated and dried to give 8-azabicyclo[3.2.1]octan-3-ol hydrochloride salt (71 mg, 100% yield). MS (EI) for C7H13NO: 128 (MH+).

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; EXELIXIS, INC.; AAY, Naing; BLAZEY, Charles, M.; BOWLES, Owen, Joseph; BUSSENIUS, Joerg; CURTIS, Jeffry, Kimo; DEFINA, Steven, Charles; DUBENKO, Larisa; HARRIS, Jason, R.; JACKSON-UGUETO, Eileen, E.; KIM, Angie, Inyoung; MANALO, Jean-claire, Limun; PACK, Michael; PETO, Csaba, J.; RICE, Kenneth, D.; TSANG, Tsze, H.; WANG, Longcheng; WO2010/138490; (2010); A1;,
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Amide – an overview | ScienceDirect Topics

Electric Literature of 362670-09-5,Some common heterocyclic compound, 362670-09-5, name is N1-Boc-5-methoxy-1,2-benzenediamine, molecular formula is C12H18N2O3, 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.

Example M51 {5-Methoxy-2-[3-oxo-3-(3-pyridin-3-yl-phenyl)-propionylamino]-phenyl}-carbamic acid tert-butyl ester The title compound was prepared from (2-Amino-5-methoxy-phenyl)-carbamic acid tert-butyl ester (Example J12) (179 mg, 0.75 mmol) and 3-oxo-3-(3-pyridin-3-yl-phenyl)-propionic acid tert-butyl ester (Example K1) (223 mg, 0.75 mmol) according to the general procedure M. Obtained as a light brown foam (256 mg). MS (ISN) 460.3 [(M-H)-].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route N1-Boc-5-methoxy-1,2-benzenediamine, its application will become more common.

Reference:
Patent; Adam, Geo; Goetschi, Erwin; Wichmann, Juergen; Woltering, Thomas Johannes; US2003/166639; (2003); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Related Products of 17193-28-1, These common heterocyclic compound, 17193-28-1, name is 1-Amino-1-cyclopentanecarboxamide, 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.

General procedure: HATU (90 mg, 0.24 mmol) was added to a solution of 1g (60 mg, 0.19) in DMA (0.75 mL) at 0 C. After 20 min, tert-butylamine (20 mg, 0.28) and DIPEA (50 mg, 0.38 mmol) in DMA (0.4 mL) were added. The reaction mixture was stirred at rt for 20 hrs. The reaction mixture was quenched with aqueous TFA (4%, 0.4 mL), then, extracted with EtOAc (10 mL). The organic layer was washed with water and brine, concentrated in vacuo, then, purified by reverse phase chromatography eluted with ACN and water, and dried using lyophilization to afford the title product as white solid. ESI-MS, m/z 360 (MH)+.

The synthetic route of 17193-28-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VenatoRx Pharmaceuticals, Inc.; BURNS, Christopher J.; COBURN, Glen; LIU, Bin; YAO, Jiangchao; BENETATOS, Christopher; BOYD, Steven A.; CONDON, Stephen M.; HAIMOWITZ, Thomas; US2019/375708; (2019); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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. Formula: C9H20N2O3

Step 1t-Butyl (2-(2-aminoethoxy)ethyl)carbamate (204 mg, 1 mmol) was dissolved in saturated aq. NaHCO3 (1 0 mL). The solution was cooled to 0 C. Methyl-2,5-dioxo-2,5- dihydro-1 H-pyrrole-1 -carboxylate (155 mg, 1.0 mmol) was then added. The reaction was stirred for 1 .5 h at 0 C. The pH was adjusted to 1 -2 with 2M HCl, and the mixture was extracted with EtOAc (3 X 20 mL). The combined organic phases was washed with brine, dried over MgSO4, filtered, and concentrated. The residue was purified by ISCO using a 0-4% gradient of MeOH in DCM to obtain tert-butyl (2-(2-(2,5-dioxo-2,5-dihydro-1 H-pyrrol- 1 -yl)ethoxy)ethyl)carbamate. 1H NMR (400 MHz, CD3OD): 6.82 (s, 2H), 3.68 (t, J = 5.4 Hz, 2H), 3.59 (t, J = 5.4 Hz, 2H), 3.46 (t, J = 5.6 Hz, 2H), 3.1 8-3.14 (m, 2H), 1.43 (s, 9H). MS m/z 1 85.1 (M+1 -Boc). Retention time 0.918 min.

The synthetic route of 127828-22-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; GEIERSTANGER, Bernhard; GRUNEWALD, Jan; OU, Weijia; PAN, Shifeng; UNO, Tetsuo; WAN, Yongqin; WANG, Xing; WO2015/189791; (2015); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics