Tag: M.W=200-300

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. 50487-72-4, name is N,N-Diallyl-4-methylbenzenesulfonamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Quality Control of N,N-Diallyl-4-methylbenzenesulfonamide

General procedure: A solution of 18 (0.001-0.0025 mmol, 1.00 mol%-10.0 mol%) was added to a solution of alkene (0.10 mmol) in toluene (0.10 mL; 1.0 M) under nitrogen. The resulting mixture was stirred at 100 C for 2-12 h. Then, the solvent was removed under reduced pressure to yield a crude product, which was purified by flash chromatography (c-hexane-CH2Cl2) to remove the Ru residue. Conversions were obtained as confirmed by 1H NMR spectroscopy by comparing the ratios of the integrals of the starting materials with those of the products. The catalytic activities of ruthenium carbyne 18 to a variety of substrates are shown in Table 1.

The synthetic route of 50487-72-4 has been constantly updated, and we look forward to future research findings.

Reference:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 118753-70-1, A common heterocyclic compound, 118753-70-1, name is tert-Butyl bis(2-chloroethyl)carbamate, molecular formula is C9H17Cl2NO2, 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.

(4-Chloro-2-fluorophenyl)acetonitrile (2.3 g, 13.7 mmol, 1.0 equiv) was added to a suspension of NaH (2.1 g, 52.5 mmol, 3.8 equiv) in DMSO (20 mL) at 23 C. The resulting yellow suspension was stirred for 10 min and the color turned red-brown. Boc-N(CH2CH2Cl) (N,N-bis(2-chloroethyl)-t-butylcarbamate) (3.7 g, 15.3 mmol, 1.1 equiv) in DMSO (20 mL) was added to the reaction mixture (bubbling observed) and the resulting suspension was heated to 85 C. with stirring for an additional 1.5 hours. The reaction mixture was cooled to 23 C. then poured onto a 1:1 mixture of ethyl acetate and hexanes (300 mL). The organic fraction was washed with water (100 mL) and a saturated aqueous solution of NaCl (100 mL). The organic layer was dried over anhydrous sodium sulfate. The dried solution was then filtered and the filtrate was concentrated. The residue was purified by flash silica chromatography (0%-30% ethyl acetate in hexanes) to afford the bis-alkylation product 1,1-dimethylethyl 4-(4-chloro-2-fluorophenyl)-4-cyano-1-piperidinecarboxylate (1.9 g, 5.6 mmol, 38%) as a yellow crystalline solid. MS (ES) m/e 239 [M-Boc+H]+.

The synthetic route of 118753-70-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Eidam, Hilary Schenck; Haile, Pamela A.; Hughes, Terry Vincent; Sehon, Clark A.; US2008/318990; (2008); 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

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

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

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

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

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. 108448-77-7, name is (1R)-(+)-2,10,Camphorsultam belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: (1R)-(+)-2,10,Camphorsultam

EXAMPLE 3; (E)-3-Benzyloxypropenoyl-(2’S)-bornane-10,2-sultam (Scheme 3, 3-3); To a solution of (E)-3-benzyloxyacrylic acid (1.74 kg, 9.88 mol) and dichloromethane (20 L) is added thionyl chloride (1.75 kg, 14.7 mol) over a period of 30 min. The reaction mixture is heated at reflux and the SO2 and HCl generated are scrubbed through a solution of aqueous NaOH. After 4 h (reaction progress is monitored by 1H NMR analysis), the solvent is removed under vacuum and the residual thionyl chloride is removed under vacuum overnight to give 2.00 kg (104%) of the desired acid chloride 3-2. To a solution of camphor sultam (1.72 kg, 7.98 mol) in THF (16 L) at -40 C. is added methyl magnesium bromide (2.79 L, 8.38 mol; 3M solution in ether) at a dropwise rate while maintaining the internal temperature between -30 C. and -40 C. The reaction mixture is stirred for an additional hour at 40 C. To the anion at -40 C. is added slowly, acid chloride 3-2 (1.92 kg, 96% purity based upon the use of acid, 9.4 mol) in THF (8 L) while maintaining the internal temperature below -25 C. The reaction mixture is further stirred between -30 C. and -40 C. for 1 h and allowed to warm to +10 C. over a period of 5-6 h. The reaction mixture is then quenched with saturated aqueous NH4Cl (16 L). The aqueous layer is separated and extracted twice with ethyl acetate (10 L). The combined organic layers are washed with saturated aqueous sodium carbonate (20 L) and brine (20 L). The organic layer is filtered through a pad of anhydrous MgSO4 and concentrated under vacuum to dryness to furnish 3.12 kg of the crude product 3-3. The crude product is taken up in ethyl acetate (8.3 L) and heated to 60 C. to dissolve the crude residue. The homogenous solution is diluted slowly with hexanes (30 L) while maintaining the solution at reflux. The reaction mixture is kept in a cold room for 16 h at 4 C. The crystalline material that separated is collected by filtration and washed with hexanes to give 1.906 kg (60%) of the desired product 3-3. The filtrate also contains the product, but no attempts are made to recover this material from the filtrate.

The synthetic route of 108448-77-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BioCryst Pharmaceuticals, Inc.; US2006/128789; (2006); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 782-45-6, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 782-45-6 name is 4-Amino-N-phenylbenzamide, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

General procedure: A solution of triphosgene (1 eq) in 5 mL dry THF was cooled to -78C. A solution of 4-(4-morpholin-4-yl-pyrido[2,3-d]pyrimidin-2-yl)-phenylamine HCl salt (3 eq) and N,N-diisopropylethylamine (4.8 eq) in dry THF (5 mL) was added dropwis to the triphosgene solution. The mixture was warmed to room temperature and stirred for 50 min. A solution of the second amine (3 eq.) and N,N-diisopropylethylamine (2.5 eq) in dry THF (5 mL) was added dropwise. The reaction mixture was stirred for 48-72 h. The solvent was removed under reduced pressure then saturated aqueous sodium bicarbonate solution (5 mL) was added to the residue to neutralize any acid. Then the solvent was removed under reduced pressure. The crude product was dissolved in 3 mLof DMSO, filtered and purified reversed phase HPLC (15 min gradient acetonitrile in water, 0.1% trifluoroacetic acid or formic acid as a m odifier).The pure product was obtained as trifluoroacetate or formate salt.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Amino-N-phenylbenzamide, and friends who are interested can also refer to it.

Reference:
Article; Al-Ashmawy, Aisha A.K.; Ragab, Fatma A.; Elokely, Khaled M.; Anwar, Manal M.; Perez-Leal, Oscar; Rico, Mario C.; Gordon, John; Bichenkov, Eugeney; Mateo, George; Kassem, Emad M.M.; Hegazy, Gehan H.; Abou-Gharbia, Magid; Childers, Wayne; Bioorganic and Medicinal Chemistry Letters; vol. 27; 14; (2017); p. 3117 – 3122;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Related Products of 177906-48-8, A common heterocyclic compound, 177906-48-8, name is trans-N-Boc-1,4-cyclohexanediamine, molecular formula is C11H22N2O2, 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 33; {4-[3-(6-Bromo-pyridin-2-yl)- l-(2-trimethylsilanyl-ethoxymethyl)-lH-pyrazolo[3,4- d]pyrimidin-6-ylamino]-cyclohexyl}-carbamic acid tert-butyl ester; The mixture of 3-(6-bromo-pyridin-2-yl)-6-chloro- l-(2-trimethylsilanyl-ethoxymethyl)- lH-pyrazolo[3,4-d]pyrimidine (from Example 31 supra) (2.65 g, 6.01 mmol), tert-butyl (lr,4r)- 4-aminocyclohexylcarbamate (1.53 g, 7.14 mmol) and Et3N (1.4 mL, 9.7 mmol) in IPA (60 mL) was heated at reflux for 16 hours. After cooling to room temperature, the reaction mixture was filtered and solid dried to give {4-[3-(6-bromo-pyridin-2-yl)- l-(2-trimethylsilanyl- ethoxymethyl)-lH-pyrazolo[3,4-d]pyrimidin-6-ylamino]-cyclohexyl}-carbamic acid tert-butyl ester as white powder. (Yield 3.3 g, 89%).

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; F. HOFFMANN-LA ROCHE AG; LIU, Wenjian; LUK, Kin-Chun Thomas; ZHANG, Xiaohu; WO2012/98068; (2012); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics