Category: amides-buliding-blocks

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;,
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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 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;,
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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;,
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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;,
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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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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;,
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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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24036-52-0, name is 6-Bromo-2H-1,4-benzoxazin-3(4H)-one, 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. Recommanded Product: 6-Bromo-2H-1,4-benzoxazin-3(4H)-one

6-bromo-3,4-dihydro-2H-benzo[6] [l,4]oxazine (2): To a stirred solution of 6- bromo-2H-benzo[6][l,4]oxazin-3(4H)-one (7 g, 30.8 mmol) in THF (20 mL) was added 1M borane in THF (15.41 mL) at 0 C and stirred for 3 h at reflux temperature. After completion of the reaction, methanol (2 mL) was added to the reaction mixture at 0 C and stirred for 2 h at reflux. After completion of the reaction, cone. HC1 (2 mL) was added to reaction mixture at 0 C and again stirred for 2 h at reflux. The reaction mixture was then neutralized with 2N NaOH solution at 0 C and extracted with ethyl acetate. The combined organic layer was washed with water and brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The crude compound was purified by column chromatography (100-200 mesh silica gel, 15% ethyl acetate in pet. ether as eluent) to afford 2 (3.2 g, 49% yield) as a brown solid. MS m/z (M+H): 214.4

The synthetic route of 24036-52-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CELGENE AVILOMICS RESEARCH, INC.; ALEXANDER, Matthew David; MCDONALD, Joseph John; NI, Yike; NIU, Deqiang; PETTER, Russell C.; QIAO, Lixin; SINGH, Juswinder; WANG, Tao; ZHU, Zhendong; WO2014/149164; (2014); A1;,
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Reference of 146651-75-4, The chemical industry reduces the impact on the environment during synthesis 146651-75-4, name is tert-Butyl (2-aminophenyl)carbamate, I believe this compound will play a more active role in future production and life.

Example 6; Ethyl l-methyl-8-(2-(^-butoxycarbonylaminophenylamino)-4,5-dihydro-lH- pyrazolo[4,3-h]quinazoline-3-carboxylate (A12BlC2Z); Palladium acetate [Pd(OAc)2] (101 mg, 0.45 mmol), (+)-BINAP (280 mg, 0.45 mmol) and dimethylformamide (65 niL) were charged to a round-bottom flask flushed with argon. The flask was evacuated and backfilled with argon. The mixture was stirred under argon for 30 minutes and added to a mixture of 2-(t- butoxycarbonylamino)aniline (2.6 g, 12.5 mmol), ethyl 8-iodo-l-methyl-4,5-dihydro- lH-pyrazolo[4,3-h]quinazoline-3-carboxylate (1.6 g, 4.16 mmol), and potassium carbonate (5.74 g, 41.6 mmol) in dimethylformamide (50 mL). The resulting mixture was stirred at 700C for 6 hours under argon. After cooling to room temperature, the reaction mixture was filtered on a pad of celite. The solvent was concentrated, the crude solid was purified by flash chromatography on silica gel (eluant: hexane/ethyl acetate 60/40) to afford 1.18 g (61% yield) of the title compound. 1H NMR (400 MHz, DMSO- d6) delta ppm 1.32 (t, J=I lambda Hz, 3 H) 1.46 (s, 9 H) 2.84 (m, 4 H) 2.96 (m, 2 H) 4.20 (s, 3 H) 4.30 (q, J= 7.1 Hz, 2 H) 7.12 (m, 2 H) 7.51 (m, 1 H) 7.71 (m, 1 H) 8.38 (s, 1 H) 8.65 (s, 1 H) 8.60 (s, 1 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, tert-Butyl (2-aminophenyl)carbamate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NERVIANO MEDICAL SCIENCES S.r.l.; WO2008/74788; (2008); A1;,
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Application of 1012884-46-6, 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. 1012884-46-6, name is 11-Chloro-2-methyl-2,3-dihydro-1H-dibenzo[2,3:6,7]oxepino[4,5-c]pyrrol-1-one belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a mixture of magnesium(19.5 grams) and iodine(0.8 grams) in 1000 ml of methanol was added 40 grams of 1 l-chloro-2,3-dihydro-2-methyl-lH-dibenz[2,3:6,7] oxepino [4,5-c] pyrrol- 1 -one at 25-30C and stirred the reaction mixture for 30 minutes at 25-30C. Heated the reaction mixture to reflux temperature and stirred for 1 hr at reflux. After completion of the reaction, the reaction mixture was cooled to 25-30C and water (400 ml) was added. Adjusted the pH of the reaction mixture to 6.4 by using 20 % dil. HC1 at 10-15C. Ethyl acetate (600 ml) was added to the reaction mixture and stirred for 30 minutes. Both the organic and aqueous layers were separated and the aqueous layer was extracted with ethyl acetate. The organic layers were combined and washed with 10% NaCl solution. Distilled off the solvent completely under reduced pressure. Isopropyl alcohol (120 ml) was added to the obtained residue. The reaction mixture was cooled to 0-5C and stirred for 2 hrs. Filtered the obtained solid, washed with isopropyl alcohol and dried to get the title compound. Yield: 21 grams.

The synthetic route of 11-Chloro-2-methyl-2,3-dihydro-1H-dibenzo[2,3:6,7]oxepino[4,5-c]pyrrol-1-one has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MSN LABORATORIES LIMITED; SATYANARAYANA REDDY, Manne; THIRUMALAI RAJAN, Srinivasan; ESWARAIAH, Sajja; MADHU, Elevathingal Nicholas; SATYANARAYANA, Komati; SEETHA RAMA SARMA, Peri; WO2012/38975; (2012); A2;,
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