Author: Jessica.F

Adding a certain compound to certain chemical reactions, such as: 96-30-0, name is 2-Chloro-N-methylacetamide, 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 96-30-0, Application In Synthesis of 2-Chloro-N-methylacetamide

The compound prepared in Reference Example 20 (50 mg)In DMF (0.5 mL)Potassium carbonate (33 mg)And tetrabutylammonium iodide(4.4 mg),Subsequently, 2-chloro-N-methylacetamide(25.7 mg) at room temperature.The reaction mixture was stirred at 50 C. overnight.The reaction mixture was diluted with ethyl acetate,Saturated ammonium chloride aqueous solution and water were added,And extracted with ethyl acetate. The obtained organic layer was washed with water,Washed with 20% brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure.The obtained residue was purified by silica gel column chromatography (Yamazen automatic purification device) to obtain the title compound having the following physical property values(51 mg).

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, 2-Chloro-N-methylacetamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Ono Pharmaceutical Co., Ltd.; Asada, Masaki; Tani, Masaya; Hiroshi, Masaya; Higuchi, Satoru; Fuchibe, Kazuhiro; Oikawa, Rei; Otani, Toru; Takano, Hiroshi; (116 pag.)JP2018/87189; (2018); A;,
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Synthetic Route of 154350-29-5, 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. 154350-29-5, name is Cyclopropanesulfonamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a toluene 85ml solution of (1R, 5S, 6r)-tert- butyl 6- (3-bromophenyl) -6-ethyl-3-azabicyclo [3.1.0] hexane-3-carboxylate8.54g (23.3mmol) obtained in Reference Example 1- (b), under an argonatmosphere, with stirring at room temperature, cyclopropanesulfonamide3.67g (30.3mmol), potassium carbonate 4.51g (32.6mmol), bis (eta3- allyl -mu-chloro palladium) 0.170g (0.465mmol) and tert- butyl XPhos0.600g (1.41mmol)were added, and the mixture was stirred for 1 hour at 110 .After completion of the reaction, water was added to the reaction mixture, andthe mixture was extracted with toluene. The organic layer was dried over anhydrous magnesium sulfate, andconcentrated under reduced pressure. The residue was subjected to silica gelcolumn chromatography (eluent hexane: ethyl acetate = 80: 20 ? 70: 30 (V / V)),and the fractions containing the desired product were concentrated underreduced pressure, and the precipitated solid was sonicated with a solution ofhexane: acetic acid ethyl = 1: 1 (V / V) and stirred, and by filtration, thetitle compound 7.86g as a white solid (83percent yield) was obtained.

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, Cyclopropanesulfonamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SANWA KAGAKU KENKYUSHO COMPANY LIMITED; UBE INDUSTRIES,LIMITED; TANIKO, KAORI; MIYAZAWA, TOSHIYUKI; KANEKO, TATSUROH; KURUMAZUKA, DAISUKE; HARADA, SATOKO; IZUCHI, TOHRU; OKABE, MORIO; IWAMURA, RYO; TSUZAKI, YASUNORI; SETOGUCHI, HIROYUKI; IMURA, YUUKI; AKAZA, HIROTO; SHIMIZU, MOTOHISA; KIMURA, TOMIO; (73 pag.)JP5860192; (2016); B2;,
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These common heterocyclic compound, 402-46-0, name is 4-Fluorobenzenesulfonamide, 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 4-Fluorobenzenesulfonamide

EXAMPLE 11; Preparation of racemic (2’S, 3S, 4’R)-6-chloro-4′-{5-chloro-2-[1-(4-fluoro-benzenesulfonylaminocarbonyl)-cyclobutoxy]-phenyl}-2′-(5-fluoro-2-methyl-phenyl)-spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione; A solution of racemic (2’S, 3S, 4’R)-6-chloro-4′-[5-chloro-2-(1-hydroxycarbonyl-cyclobutoxy)-phenyl]-2′-(5-fluoro-2-methyl-phenyl)spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione (50 mg, 0.086 mmol) and CDI (28 mg, 0.17 mmol) in DMF (0.5 mL) was heated at 60 C. for 30 min, and then cooled to root temperature. To this solution was added a mixture of 4-fluoro-benzenesulfonamide (175 mg, 1 mmol) and NaH (40 mg, 60%, 1 mmol) in DMF (1 mL). The resulting mixture was stirred at room temperature for 10 min, purified by prep-HPLC to give the title compound as a white solid (20 mg).

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

Reference:
Patent; Chen, Li; Han, Xingchun; He, Yun; Yang, Song; Zhang, Zhuming; US2009/163512; (2009); 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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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;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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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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,
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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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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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