Month: February 2021

Application of 149990-27-2,Some common heterocyclic compound, 149990-27-2, name is tert-Butyl but-3-yn-1-ylcarbamate, molecular formula is C9H15NO2, 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.

Ethyl 2-isocyanoacetate (4.30 mL, 39.34 mmol) was added slowly to tert-butyl but-3-yn-1-ylcarbamate (9.99 g, 59.01 mmol) and Silver carbonate (1.085 g, 3.93 mmol) in 1,4-dioxane (18 mL) at 80C over a period of 10 minutes under nitrogen. The resulting solution was stirred at 80 C for hours. A LCMS indicated the presence of the desired material and also the by-product 6. The reaction mixture was concentrated, dissolved in DCM and filtered. The reaction was purified by flash silica chromatography, elution gradient 0 to 25% EtOAc in heptane. Pure fractions were evaporated to dryness to afford ethyl 3-(2-((tert-butoxycarbonyl)amino)ethyl)-1H-pyrrole-2-carboxylate (5.51 g, 49.6 %) as a colourless oil; MS (ES-) m/z: 281 (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 tert-Butyl but-3-yn-1-ylcarbamate, its application will become more common.

Reference:
Article; Greenwood, Ryan; Yeung, Kay; Tetrahedron Letters; vol. 57; 51; (2016); p. 5812 – 5814;,
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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. 630-22-8, name is 2,2-Dimethylpropanethioamide, A new synthetic method of this compound is introduced below., Product Details of 630-22-8

Step (b) ethyl 2-tert-butylthiazole-4-carboxylateEthyl 3-bromo-2-oxopropanoate (6.20 mL, 49.40 mmol) was added very carefully to a stirred solution of 2,2-dimethylpropanethioamide (5.79 g, 49.40 mmol) in ethanol (60 mL). The solution was then heated under reflux for 16h. After cooling, the reaction mixture was diluted with EtOAc, washed with saturated aqueous sodium bicarbonate solution and evaporated in vacuo. Purification by silica gel chromatography (Biotage, 10Og) eluting with EtOAc: iso- hexane, 1 :10 gave the sub-title compound as a yellow oil. Yield: 6.56 g1U NMR (300 MHz, CDCl3) delta 8.03 (s, IH), 4.40 (q, J= 7.1 Hz, 2H), 1.48 (s, 9H), 1.39 (t, J =6.3 Hz, 3H).MS: [M+H]+=214 (MultiMode+)

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; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/144494; (2009); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Related Products of 39549-79-6, 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 39549-79-6 as follows.

General procedure: Sodium hydrogen sulfite (4 mmol) was added to a solution of anthranilamide 1 (2 mmol) and benzaldehyde 2 (2 mmol) in N,N- dimethylacetamide (5 mL). The mixture was heated under continuous stirring at 150 o C for 2-3 h and poured into ice water. The precipitate was then filtered, washed with water followed byethanol, and dried to yield the 2-arylquinazolinones 3-31.#10;#10;

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; Khadka, Daulat Bikram; Tran, Giap Huu; Shin, Somin; Nguyen, Hang Thi Minh; Cao, Hue Thi; Zhao, Chao; Jin, Yifeng; Van, Hue Thi My; Chau, Minh Van; Kwon, Youngjoo; Le, Thanh Nguyen; Cho, Won-Jea; European Journal of Medicinal Chemistry; vol. 103; (2015); p. 69 – 79;,
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Reference of 24243-71-8, A common heterocyclic compound, 24243-71-8, name is Propane-1-sulfonamide, molecular formula is C3H9NO2S, 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.

[0171] NaH (60% in mineral oil, 80 mg, 1.99 mmol) was slowly added to a solution of propane-i-sulfonamide (226 mg, 1.84 mmol) in DMF (20.0 mL) at 0 C. The reaction mixture was degassed with N2 and stirred at room temperature for 60 mm. Then 9-(3-fluoro- 2-nitrophenoxy)-2,3-dihydroimidazo[i,2-cjquinazoline (500 mg, 1.53 mmol) was added and the mixture was stirred at 80 C overnight under N2. The resulting mixture was evaporated and the residue was purified by flash column (ACN/H20) to afford N-(3-((2,3- dihydroimidazo [1 ,2-cjquinazolin-9-yl)oxy)-2-nitrophenyl)propane- i-sulfonamide (240 mg, 37% yield) as a yellow solid. ?H NMR (400 MHz, DMSO-d6): 8.24 (s, 1H), 7.67 (d, J = 8.8 Hz, 1H), 7.57-7.51 (m, 2H), 7.39-7.32 (m, 2H), 6.68 (d, J= 7.2 Hz, 1H), 4.34 (t, J= 10.0 Hz, 2H), 4.00 (t, J= 10.0 Hz, 2H), 2.96 (t, J= 7.6 Hz, 2H), 1.72-1.66 (m, 2H), 0.96 (t, J= 7.6 Hz, 3H). LCMS (M+H) mlz: 430.1.

The synthetic route of 24243-71-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ABM THERAPEUTICS, INC.; CHEN, Chen; (154 pag.)WO2019/60611; (2019); A1;,
Amide – Wikipedia,
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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. 96-30-0, name is 2-Chloro-N-methylacetamide, This compound has unique chemical properties. The synthetic route is as follows., Safety of 2-Chloro-N-methylacetamide

Method W: 2-(6-(2-(methylamino)-2-oxoethoxy)-2-(pyridin-3-yl)quinazolin-4-ylamino)benzamide The suspension of 2-(6-hydroxy-2-(pyridin-3-yl)quinazolin-4-ylamino)benzamide (synthesized as described in Scheme 24) (0.20 g, 0.56 mmol), 2-chloro-N-methylacetamide (90 mg, 0.80 mmol), cesium carbonate (0.37 g, 1.12 mmol) and potassium iodide (0.19 g. 1.12 mmol) in DMF (10 mL) was stirred for 4 days at room temperature. Water (20 mL) was added to the mixture. The resultant solid was collected by filtration. The obtained solid was washed with CH2Cl2-THF (1:1) solution and dried to give 0.11 g of 2-(6-(2-(methylamino)-2-oxoethoxy)-2-(pyridin-3-yl)quinazolin-4-ylamino)benzamide as pale brown solid (46%). LCMS m/z=429 (M+1) (Method C) (retention time=1.65 min). 1H NMR (300 MHz, DMSO) delta 9.58 (s, 1H), 9.12 (d, J=8.4 Hz, 1H), 8.82-8.64 (m, 2H), 8.48 (s, 1H), 8.32-8.17 (m, 1H), 8.10-7.87 (m, 3H), 7.81-7.49 (m, 4H), 7.21 (t, J=7.5 Hz, 1H), 4.66 (s, 2H), 2.71 (d, J=4.5 Hz, 3H).

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 96-30-0.

Reference:
Patent; Suzuki, Masaki; Kondo, Kazumi; Kurimura, Muneaki; Valluru, Krishna Reddy; Takahashi, Akira; Kuroda, Takeshi; Takahashi, Haruka; Fukushima, Tae; Miyamura, Shin; Ghosh, Indranath; Dogra, Abhishek; Harriman, Geraldine; Elder, Amy; Shimizu, Satoshi; Hodgetts, Kevin J.; Newcom, Jason S.; US2015/307477; (2015); A1;,
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 22808-73-7 as follows. name: Methyl 4-sulfamoylbenzoate

4-Hvdroxymethyl-benzenesulfonamide; To a solution of 5.2 g 4-sulfamoyl-benzoic acid methyl ester in 100 ml. THF and 1.44 ml. MeOH, 0.77 g lithium borohydride was added portion-wise over a period of 10 minutes. The mixture was heated at reflux overnight, cooled to room temperature, and poured onto ice containig 100 ml. 1 N HCI. The mixture was extracted with EtOAc, and the organic layer was dried over MgSO4 and concentrated under reduced pressure. The residue was purified by automated flash chromatography (EtOAc/Hexane 1 :1 ) to give 0.75 gram (17%) of product. 1H NMR (400 MHz, DMSO-de) delta 4.57 (d, J=5.81 Hz, 1 H), 5.38 (t, J=5.81 Hz, 1 H), 7.48 (d, J=8.34 Hz, 2H), 7.78 (d, J=8.34 Hz, 2H).

According to the analysis of related databases, 22808-73-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SOLVAY PHARMACEUTICALS B.V.; WO2009/115515; (2009); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 190900-21-1, These common heterocyclic compound, 190900-21-1, name is tert-Butyl 5-oxo-1,4-diazepane-1-carboxylate, 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.

(1171) [00391] To a mixture of 2-(4-bromophenyl)ethanamine (10.0 g, 50.0 mmol) and saturated aqueous sodium bicarbonate (375 ml) was slowly added Cbz-Cl (10.3 g, 8.56 ml, 60.0 mmol). The reaction mixture was allowed to stir at RT for 1 hour (a white precipitate forms) and then extracted with EtOAc (2 x 200 mL). The organic layers were combined, washed with water (100 mL) and brine (100 mL), dried over sodium sulfate, filtered, and concentrated in vacuo. The resulting crude product was purified by FCC eluting with 5 – 20% EtOAc in hexanes to afford benzyl (4-bromophenethyi)earbamate as a white solid (16.7g, 100%). LCMS (ESI, m/z): 334, 336 [M ] [J .

The synthetic route of 190900-21-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FORMA THERAPEUTICS, INC.; GUERIN, David Joseph; BAIR, Kenneth W.; CARAVELLA, Justin A.; IOANNIDIS, Stephanos; LANCIA JR., David R.; LI, Hongbin; MISCHKE, Steven; NG, Pui Yee; RICHARD, David; SCHILLER, Shawn E. R.; SHELEKHIN, Tatiana; WANG, Zhongguo; (365 pag.)WO2017/139778; (2017); A1;,
Amide – Wikipedia,
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Related Products of 563-83-7, A common heterocyclic compound, 563-83-7, name is Isobutyramide, molecular formula is C4H9NO, 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: A mixture of cobalt(II) oxalate dihydrate(Sigma-Aldrich, 0.294 mmol), Cs2CO3 (2.94 mmol), pyrrolidinoneor aliphatic amide (1.47 mmol), DMEDA (0.588 mmol),distilled H2O (0.3 mL) and aryl halide (2.205 mmol) were addedto an 8.0-mL reaction vial fitted with a Teflon-sealed screw cap.The reaction mixture was stirred under air in a closed system at120 C and 130 C, respectively for 24 h. The heterogeneousmixture was subsequently cooled to r.t. and diluted withCH2Cl2. The combined organic extracts were dried over anhydNa2SO4, filtered and the solvent was removed under reducedpressure. The crude product was loaded into the column usingminimal amounts of CH2Cl2 and was purified by silica gel column chromatography to afford the N-arylated product. Theidentity and purity of products were confirmed by 1H NMR and13C NMR spectroscopic analysis.

The synthetic route of 563-83-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Tan, Bryan Yong-Hao; Teo, Yong-Chua; Synlett; vol. 26; 12; (2015); p. 1697 – 1701;,
Amide – Wikipedia,
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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. 24451-15-8, name is Ethyl 2-((4-bromophenyl)amino)-2-oxoacetate, A new synthetic method of this compound is introduced below., Computed Properties of C10H10BrNO3

General procedure: A methanolic solution of TBAOH (1.0 M, 2.4 mmol) was addeddirectly to a one-neck round flask suspension of the correspondingN-substituted oxamate proligand (0.6 mmol) in 10 mL of acetonitrileat 60 C. Then, an aqueous solution of K2[PdCl4] (100 mg,0.3 mmol in 5 mL of water) was added dropwise to the reactionmixture and resulting basic solution was heated at 60 C for 10 hunder continuous stirring. The solution was allowed to evaporateat room temperature. X-ray quality yellow prisms were grownup after two weeks (2) and a couple of days (3 and 4). Their formulaswere determined by X-ray diffraction on single crystals.2: Yield: 90%

The synthetic route of 24451-15-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Fortea-Perez, Francisco Ramon; Neve, Francesco; Armentano, Donatella; De Munno, Giovanni; Stiriba, Salah-Eddine; Julve, Miguel; Inorganica Chimica Acta; vol. 443; (2016); p. 267 – 273;,
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Synthetic Route of 22503-72-6, These common heterocyclic compound, 22503-72-6, name is 7-Chloro-3-methyl-3,4-dihydro-2H-benzo[e][1,2,4]thiadiazine 1,1-dioxide, 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: To an ice-cooled solution of 2,3-dihydrobenzothiadiazine 1 or 6-13(1.0 mmol) in CH2Cl2 (10 mL) was added dropwise an excess ofMCPBA (739 mg, 3.0 mmol, 70%) in CH2Cl2 (10 mL) previouslycooled in an ice bath. The mixture was allowed to gradually warmto r.t., with stirring, over 12 h. TLC and LC-MS analyses were usedto monitor reaction progress. The solution was then evaporated todryness, in vacuo at r.t., to give the crude material. The reactionmixture was purified by chromatography on silica gel (petroleumether-EtOAc, 60:40).

The synthetic route of 22503-72-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Cannazza, Giuseppe; Perrone, Serena; Rosato, Francesca; D’Accolti, Lucia; Parenti, Carlo; Troisi, Luigino; Synthesis; vol. 46; 7; (2014); p. 962 – 966;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics