Category: amides-buliding-blocks

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

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

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

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

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

Synthetic Route of 627-12-3, 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. 627-12-3, name is Propyl carbamate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: CuI (10mol%) and EDA (10mol%) were added to a mixtureof O-alkyl carbamate (1mmol), NaOtBu (1.5mmol) and aryl halide (1mmol) in 2mL toluene and the mixture wasstirred for the appropriate time, which was determined byTLC monitoring, at 100C. After completion of the reaction,the catalyst was removed by filtration and 20mL H2Owas added to the filtrate. The resultant mixture was extractedwith CHCl3.Then the organic phase was washed with water(2 ¡Á 10mL) and dried over anhydrous Na2SO4.After evaporationof CHCl3under reduced pressure, the correspondingcrude product was purified by flash chromatography to givethe desired pure cross-coupling product in good to excellentyield. In the case of using arylboronic acids as couplingpartners, Cu(OAc)2 was employed instead of CuI.

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, Propyl carbamate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Sardarian, Ali Reza; DindarlooInaloo, Iman; Zangiabadi, Milad; Catalysis Letters; vol. 148; 2; (2018); p. 642 – 652;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Some common heterocyclic compound, 84713-20-2, name is Benzyl vinylcarbamate, molecular formula is C10H11NO2, 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. Recommanded Product: Benzyl vinylcarbamate

EXAMPLE 3 cis-(2-Ethyl-6-trifluoromethyl-1 2,3,4-tetrahydro-quinolin-4-yl)-carbamic Acid Benzyl Ester A one liter, four neck flask under nitrogen atmosphere was charged with N-vinyl-carbamic acid benzyl ester (27.66 g, 156 mmol, 1.0 equiv) and dry toluene (500 mL). (1-Benzotriazol-1-yl-propyl)-(4-trifluoromethyl-phenyl)-amine (50.0 g, 156 mmol, 1.0 equiv) and p-toluenesulfonic acid monohydrate (297 mg, 1.56 mmol, 0.01 equiv) were added, and the mixture heated to 70 C. After 2 h, the mixture was cooled to room temperature and transfered to a separatory funnel. Ethyl acetate (500 mL) was added. The mixture was washed 1*200 mL 1N NaOH, 1*200 mL H2O, 1*200 mL brine, and dried (MgSO4). The mixture was filtered and the solids washed 1*50 mL ethyl acetate. The filtrate was concentrated to approximately 250 mL. 500 mL toluene were added, and the mixture concentrated to approximately 500 mL. 500 mL n-heptane were added, the slurry was stirred 1 h, filtered through a Buchner funnel, and dried. cis-(2-Ethyl-6-trifluoromethyl-1,2,3,4-tetrahydro-quinolin-4-yl)-carbamic acid benzyl ester was isolated as a white powder (45.04 g, 76%): mp 155-157 C.; 1H NMR (DMSO-d6, 400 MHz) delta 0.92 (t, 3H, J=7.5 Hz), 1.5 (m, 3H), 2.00 (m, 1H), 3.35 (m, 1H), 4.77 (m, 1H), 5.07 (d, 1H, J=12.5 Hz), 5.15 (d, 1H, J=12.5 Hz), 6.35 (s, 1H), 6.61 (d, 1H, J=8.5 Hz), 7.12 (s, 1H), 7.18 (dd, 1H, J=1.9, 8.5 Hz), 7.4 (m, 5H), 7.70 (d, 1H, J=9.1 Hz); 13C NMR (DMSO-d6, 100 MHz) delta 157.03, 149.02, 137.79, 128.82, 128.23, 128.03, 125.9 (q, J=270 Hz), 125.06, 123.50, 121.73, 115.2 (q, J=31.7 Hz), 113.33, 65.85, 52.09, 47.83, 34.02, 28.68, 9.93; DEPT spectrum: quaternary carbons delta 157.03, 149.02, 137.79, 125.9, 121.73, 115.2; CH carbons delta 128.82, 128.23, 128.03, 125.06, 123.50, 113.33, 52.09, 47.83; CH2 carbons delta 65.85, 34.02, 28.68; CH3 carbon delta 9.93; IR (drifts) 3430 (m), 3303 (s), 2951 (m), 1686 (vs), 1542 (vs), 1088 (vs); MS (APCI+) m/z (rel. intensity) 379 (M+H+, 53), 228 (100); Anal. Calcd for C20H21N2O2F3: C, 63.48; H, 5.59; N, 7.40; Found: C, 63.69; H, 6.06, N, 7.36.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 84713-20-2, its application will become more common.

Reference:
Patent; Shear, Charles L.; US2002/35125; (2002); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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. 14719-21-2, name is 2,2,2-Trifluoro-N-(prop-2-yn-1-yl)acetamide, A new synthetic method of this compound is introduced below., name: 2,2,2-Trifluoro-N-(prop-2-yn-1-yl)acetamide

Add dU-I (0.7mmol, 247mg) to a single-mouth bottle, add 9.7mg CuI and 20.3mg Pd(PPh3)4 to the reaction flask, vacuum, protect with nitrogen, wrap with aluminum foil, add 2.3ml DMF, stir and dissolve. 0.2 ml of TEA was added, and trifluoroethylpropynylamine (254 mg, 1.7 mmol) was weighed and dissolved in DMF, and then added to the above reaction flask, stirred at room temperature, and allowed to react overnight. After the reaction is completed, the solvent is evaporated to dryness under reduced pressure, and then directly separated by column chromatography, and dichloromethane and methanol are mixed at a volume ratio of 20:1 as a leaching agent to obtain dU-F3.

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; Suzhou Bai Yuan Genes Co., Ltd.; Lanzhou Bai Yuan Genes Co., Ltd.; Che Tuanjie; (40 pag.)CN108752406; (2018); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics