Month: March 2021

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. 154748-63-7, name is tert-Butyl (3-hydroxycyclobutyl)carbamate, A new synthetic method of this compound is introduced below., name: tert-Butyl (3-hydroxycyclobutyl)carbamate

Step B: Tert-butyl 3-fluorocyclobutylcarbamate. To a solution tert-butyl 3-hydroxycyclobutyl – carbamate ( 1 g, 5.35 mmol) in dry DCM (20 mL) at -70 C was added DAST dropwise (l g, 0.85 mL, 1 .17 eq) under the atmosphere of N2. The mixture was then slowly warmed to room temperature and stirred overnight. The resulting mixture was washed with diluted aq. NaHC03. The organic layer was dried over anhydrous Mg2S04 and concentrated. The residue was purified by flash chromatography using petroleum ether / EtOAc (V:V, 20: 1 to 2: 1 ) as eluent to afford a white solid as the desired product. MS : 190.1 (M+ l )+.

The synthetic route of 154748-63-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AGIOS PHARMACEUTICALS, INC.; LEMIEUX, Rene M.; POPOVICI-MULLER, Janeta; TRAVINS, Jeremy M.; CAI, Zhenwei; CUI, Dawei; ZHOU, Ding; WO2015/10297; (2015); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 67442-07-3, A common heterocyclic compound, 67442-07-3, name is 2-Chloro-N-methoxy-N-methylacetamide, molecular formula is C4H8ClNO2, 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.

Isopropylmagnesium chloride (2 M in THF, 7.63 mL, 15.26 mmol) was added dropwise to a solution of 3-(benzyloxy)-5-bromopyridine (3.10 g, 1 1.74 mmol) in THF (20 mL) at 0 ¡ãC. The mixture was stirred at rt for 90 min and a solution of 2-chloro-A/-methoxy-/V-methyl- acetamide (1.78 g, 12.9 mmol) in THF (20 mL) was added dropwise. The mixure was stirred at rt for 1 h. NH4CI (aq, 10 percent) was added and the mixture was extracted with Et20. The combined extracts were washed with brine, dried (Na2S04) and concentrated. The residue was purified by chromatography to give the sub-title compound (1.00 g, 3.82 mmol, 33 percent).

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; ATROGI AB; PELCMAN, Benjamin; BENGTSSON, Tore; (93 pag.)WO2019/53427; (2019); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 88829-82-7, name is tert-Butyl (8-aminooctyl)carbamate, 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 88829-82-7, category: amides-buliding-blocks

3- (5-fluoro-4-oxobenzo [d] [1,2,3] triazine-3 (4H) -yl) piperidine in a solution of the compound (1 eq.) Prepared in step 1 above in DMF. Dean-2,6-dione (1 eq) and DIPEA (2.4 eq) were added. The reaction mixture was stirred at room temperature for 30 minutes and then at 90 C. for 4 hours. The resulting mixture was extracted with EtOAc. The combined organic layers were washed with brine. Then, the organic layer was dried (Na2SO4) and filtered. The solvent was removed in vacuo and the product was purified by column chromatography using MeOH / DCM 6% eluent to give the desired compound (61%) as a yellow solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, tert-Butyl (8-aminooctyl)carbamate, and friends who are interested can also refer to it.

Reference:
Patent; Korea Research Institute of Chemical Technology; Korea Research Institute of Bioscience and Biotechnology; Hwang Jong-yeon; Ha Jae-du; Cho Seong-yun; Kim Pil-ho; Lee Jeong-ok; Park Ji-hun; Kim Hyeon-jin; Park Byeong-cheol; Park Seong-gu; Kim Jeong-hun; Kim Seon-hong; (121 pag.)KR2020/24669; (2020); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Related Products of 406233-31-6, The chemical industry reduces the impact on the environment during synthesis 406233-31-6, name is 4-Fluoro-3-nitrobenzenesulfonamide, I believe this compound will play a more active role in future production and life.

General procedure: To an ice cold stirred solution of compound 4a-4u (1 eq) in anhydrousDCM (10 mL for 1 mmol of substrate), TEA (3 eq) was added dropwise and stirred for 10 min. Compound 5 (1 eq) was added slowly andstirred at RT for 16 h (precipitation was observed during the reactionprogress). TLC showed completion of reaction. The reaction mixturewas concentrated under reduced pressure. Water was added to thecrude material and stirred for 30 min. Obtained solid was filtered,washed with water and dried under vacuum. The solid was trituratedwith ethyl acetate, filtered and dried under high vacuum to affordcompound 6a-v.

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, 4-Fluoro-3-nitrobenzenesulfonamide, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Kalisha Vali; Gundla, Rambabu; Singh, Om V.; Tamboli, Yasinalli; Di Cesare Manelli, Lorenzo; Ghelardini, Carla; Al-Tamimi, Abdul-Malek S.; Carta, Fabrizio; Angeli, Andrea; Supuran, Claudiu T.; Bioorganic Chemistry; vol. 92; (2019);,
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. 579-10-2, name is N-Methylacetanilide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of N-Methylacetanilide

A solution of N-methyl-N-phenylacetamide (73.8 mmol) in dichloromethane (20 mL) was added dropwise to sulfurochloridic acid (690 mmol) at 5 C. and the resulting solution was allowed to warm to rt and was maintained 16 h. The reaction mixture was diluted with iced water (100 mL) and was extracted with dichloromethane (2*50 mL). The combined organic layers were dried (sodium sulfate) and concentrated. The residue was purified by Flash chromatography (10/1 ethyl acetate/petroleum ether) to give 4-(N-methylacetamido)benzene-1-sulfonyl chloride in 11% yield as a white solid. Data: 1H NMR (CDCl3) delta 8.09 (d, 2H), 7.48 (d, 2H), 3.38 (s, 3H), 2.17 (s, 3H).

The synthetic route of 579-10-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Memory Pharmaceuticals Corporation; US2010/22581; (2010); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 53844-02-3, 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. 53844-02-3, name is Benzyl (2-bromoethyl)carbamate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Cesium carbonate (1 eq.) was slurried in anhydrous DMF (200 mL) at room temperature. Methyl paraben (20 g) was then added to the slurry followed by N-(2- bromethyl)benzyl carbamate (1 eq.). The reaction was stirred overnight at room temperature. The reaction was then transferred to a separatory funnel and diluted with ethyl acetate (400 mL) and water (100 mL). The organic layer was subsequently washed with water (2 x 50 mL), then washed with saturated NaCl solution (50 mL). The organic layer was dried with MgSO4, filtered, and concentrated on a rotary evaporator to a white solid. The resulting material was dissolved in 2:1 methanol:water, and the pH of the solution was then brought to ~12 via the addition of 1 M LiOH solution. The reaction was stirred at room temperature overnight. The reaction was then placed on a rotary evaporator to remove most of the methanol, then diluted with water (300 mL), then adjusted to pH ~2 via the addition of concentrated HCl solution resulting in formation of a thick white precipitate. The solid was isolated via filtration through a Buchner funnel fitted with a paper filter and washed with water (3 x 100 mL). The solid was then dried under vacuum to produce Intermediate N (25g) that was used without further purification.

The synthetic route of Benzyl (2-bromoethyl)carbamate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ELYSIUM THERAPEUTICS, INC.; JENKINS, Thomas E.; HUSFELD, Craig O.; (236 pag.)WO2018/170465; (2018); 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. 1386861-46-6, name is 2-Chloro-6-methyl-N-phenylbenzamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of 2-Chloro-6-methyl-N-phenylbenzamide

General procedure: To a stirred mixture of amide (C-2) (173 mmol, 1 eq) in anhydrous THF (250 mL) at -30 C under an argon atmosphere, a solution of n-butyllithium in hexanes (432 mol, 2.5 eq) is added dropwise over 30 min while keeping inner temperature between -30 C and -10 C. The resulting mixture is then stirred at -30 C for 30 min.[00540] To a stirred mixture of (S)-tert-butyl 1-(methoxy(methyl)amino)-1-oxopropan-2-ylcarbamate(260 mmol, 1.5 eq) in anhydrous THF (250 mL) at -30 C under an argon atmosphere, a solution of isopropylmagnesium chloride in THF (286 mmol, 1.65 eq) is added dropwise over 30 min while keeping inner temperature between -30 C and -10 C. The resulting mixture is stirred at -30 C for 30 min. This solution is then slowly added to the above reaction mixture while keeping the inner temperature between -30 C and -10 C. The resulting mixture is stirred at -15 C for 1 h. The reaction mixture is quenched with water (50 mL) and then acidified with cone. HCl at -10 C – 0 C to adjust the pH to 1-3. The mixture is allowed to warm to RT and concentrated in vacuo. The residue is dissolved in MeOH (480 mL), and then cone. HCl (240 mL) is added quickly at RT. The resulting mixture is stirred at reflux for 1 h. The reaction mixture is concentrated in vacuo to reduce the volume to about 450 mL. The residue is extracted with a 2: 1 mixture of heptane and ethyl acetate (2 x 500 mL). The aqueous layer is basified with concentrated ammonium hydroxide to adjust the pH to 9-10 while keeping the inner temperature between -10 C and 0 C. The mixture is then extracted with DCM (3 x 300 mL), washed with brine, dried over MgSO4 and filtered. The filtrate is concentrated in vacuo and the residue is dissolved in MeOH (1200 mL) at RT. To this solution, D-(-)-tartaric acid (21g, 140 mmol, 0.8 eq) is added in one portion at RT. After stirring at RT for 30 min, a precipitate forms and the mixture is slurried at RT for 10 h. The solid is collected by filtration and rinsed with MeOH (3 x 50 mL). The collected solid is suspended in water (500 mL) and then neutralized with concentrated ammonium hydroxide solution at RT to adjust the pH to 9-10. The mixture is extracted with DCM (3 x 200 mL). The combined organic layers are washed with brine, dried over MgS04 and filtered. The filtrate is concentrated in vacuo to afford (S)-3-(1-aminoethyl)-isoquinolin-1(2H)-ones (C-3).

The synthetic route of 1386861-46-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; INFINITY PHARMACEUTICALS INC.; INTELLIKINE, LLC; CASTRO, Alfredo, C.; EVANS, Catherine, A.; LESCARBEAU, Andre; LIU, Tao; SNYDER, Daniel, A.; TREMBLAY, Martin, R.; REN, Pingda; LIU, Yi; LI, Liansheng; CHAN, Katrina; WO2013/12918; (2013); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 122334-37-6, These common heterocyclic compound, 122334-37-6, name is 4-Chloro-N-methoxy-N-methylbenzamide, 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.

Example 1; 3-(4-chloro-phenyl)-2-(2>4-dichloro-phenyl)-4,5,6,7-tetraliydro-2H- indazole-7-carboxylic acidpiperidin-1-ylamide (Cpd 33); To a solution of LHMDS (21 mL, 2.1 mmol) in 50 mL of anhydrous THF under a nitrogen atmosphere at -78 0C was added 2-oxo-cyclohexanecarboxylic acid ethyl ester Compound Ia (1.80 g, 10.0 mmol) in 10 mL of anhydrous THF. The resultant homogeneous mixture was left to stir at -78 0C for 40 min followed by the drop wise addition of 4-chloro-N-methoxy-N-methyl-benzamide Compound Ib (2.0 g, 10 mmol) in 10 mL of anhydrous THF. The reaction mixture was allowed to stir for 18 hours and allowed to warm to ambient temperature. The reaction mixture was quenched with water (50 mL) and the organic layer was extracted with EtOAc (200 mL) and washed with brine, separated and dried with anhydrous Na2SO4, then filtered and concentrated in vacuo to yield 3-(4-chloro-benzoyl)-2-oxo-cyclohexanecarboxylic acid ethyl ester Compound Ic (1.7 g) as an oil, which was used in the next step without further purification.

Statistics shows that 4-Chloro-N-methoxy-N-methylbenzamide is playing an increasingly important role. we look forward to future research findings about 122334-37-6.

Reference:
Patent; JANSSEN PHARMACEUTICA, NV; WO2007/95513; (2007); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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. 1171331-39-7, name is 2-Amino-N-(2,2,2-trifluoroethyl)acetamide hydrochloride, This compound has unique chemical properties. The synthetic route is as follows., Safety of 2-Amino-N-(2,2,2-trifluoroethyl)acetamide hydrochloride

To a stirred solution of (Z)-2-bromo-4-(4,4,4-trifluoro-3-(3,4,5-trichlorophenyl)but-1-en-1-yl)benzoic acid (200 mg, 0.41 mmol) in anhydrous THF (5.0 mL) was added carbonyldiimidazole (82 mg, 0.51 mmol). The mixture was heated in a 50 C. oil bath for 1.5 h, treated with 2-amino-N-(2,2,2-trifluoroethyl)acetamide hydrochloride (109 mg, 0.057 mmol) and the resulting mixture heated to reflux for 8 h. After cooling to ambient temperature, the mixture was taken up in Et2O and washed twice with aq. 5% NaHSO4 (2*) and once with sat. NaCl (1*). After dying over MgSO4, concentration in vacuo and purification by medium pressure chromatography on silica with EtOAc/Hexanes as the eluents, the title compound was obtained as a white foam (160 mg, 41%) mp 48-61 C.: 1H NMR (400 MHz, CDCl3) delta 7.58 (d, J=7.9 Hz, 1H), 7.44-7.29 (m, 3H), 7.14 (dd, J=7.9, 1.6 Hz, 1H), 6.86 (d, J=11.4 Hz, 1H), 6.76 (t, J=5.9 Hz, 1H), 6.59 (br s, 1H), 6.21-6.04 (m, 1H), 4.23 (d, J=5.5 Hz, 1H), 3.98 (qd, J=9.0, 6.5 Hz, 2H); 19F NMR (376 MHz, CDCl3) delta -69.31, -72.3; EIMS m/z 626.9 ([M+1]+).

According to the analysis of related databases, 1171331-39-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Dow AgroSciences LLC; Lo, William C.; Hunter, James E.; Watson, Gerald B.; Patny, Akshay; Iyer, Pravin S.; Boruwa, Joshodeep; US2014/171312; (2014); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 1628-29-1, name is 1-(10H-Phenothiazin-10-yl)ethanone, 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 1628-29-1, Application In Synthesis of 1-(10H-Phenothiazin-10-yl)ethanone

Under argon atmosphere,Firstly, NaOH and triethylboron are stirred to form a transparent clear solution at room temperature.The concentration is 1M/L;Then,The above triethylboron solution was successively treated with 10umol (2mol%),Amide substrate 5mmol,Triethoxysilane or polymethylhydrogensiloxane 15mmol,MTBE 2mL added to the 10mL sealed tube,It is heated and stirred in an 80C oil bath for 6 hours.The reaction is over,Exposing the reaction to air quenching,The amine product is then separated directly by column chromatography.According to the results of column chromatography separation, when using triethoxysilane or polymethylhydrogensiloxane (PMHS),The yield of the target product was:

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, 1-(10H-Phenothiazin-10-yl)ethanone, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Taizhou University; Yao Wubing; Li Rongrong; Jiang Huajiang; (10 pag.)CN107337573; (2017); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics