Month: March 2021

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. 147291-66-5, name is tert-Butyl 3-aminobenzylcarbamate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: tert-Butyl 3-aminobenzylcarbamate

Example 2.4: tert-butyl 3-acetamidobenzyIcarbamate; [0235] To a stirred solution of tert-butyl 3-aminobenzylcarbamate (Hah, Jung-Mi; Martasek, Pavel; Roman, Linda J.; Silverman, Richard B.; J. Med. Chem.; 2003, 46,1661 – 1669) (287 mg, 1.29 mmol) in CH2Cl2 (10 mL) at O0C was added Et3N (0.27 mL, 2.0 mmol) and acetyl chloride (0.10 mL, 1.4 mmol) and the resulting solution was warmed up to room temperature slowly. After further stirring of 4 h, the reaction was quenched with saturated aqueous NH4Cl. The layers were separated and the aqueous layer was extracted with CH2Cl2 (2 x 20 mL). The combined organic layer was washed with H2O, brine, dried with Na2SO4 and concentrated under reduced pressure. The residue oil was purified by column chromatography (60% EtOAc in hexanes) to provide acetamide (123.1 mg, 36%).

The synthetic route of 147291-66-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ZAPAQ, INC.; THE BOARD OF TRUSTEES OF THE UNVERSITY OF ILLINOIS; OKLAHOMA MEDICAL RESEARCH FOUNDATION; WO2006/110668; (2006); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 4563-33-1, name is Phenylmethanesulfonamide, 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 4563-33-1, COA of Formula: C7H9NO2S

(b) tert-Butyl 3-[(benzylsuIfonyI)carbamoyl]azetidine-l-carboxylateTBTU (33.71 g, 105 mmol) and TEA (30.3 g, 300 mmol) was added to a solution of 1- (tert-butoxycarbonyl)azetidine-3-carboxylic acid from above (25.89 g, assumed to contain is 100 mmol) in THF (200 mL) and the reaction was stirred at r.t for 30 minutes. 1- phenylmethanesulfonamide (17.97 g, 105 mmol) and LiCl (1.844 g, 43.5 mmol) was added and the stirring was continued at r.t over night (23 hours). The reaction was concentrated to about 1/3 was left and EtOAc (500 mL) was added and the organic phase was washed with 2 M HCl (1 x 150 mL, 2 x 50 mL), water (2 x 50 mL). Drying (MgSO4), filtration and20 evaporation of the solvent gave a brown powder (48. 6 g). The powder was slurried in 150 mL TBME and stirred 3 hours. The solids was filtered off and washed with TBME (40 mL). This procedure was repeated twice with 100 mL TBME (washing with 25 mL) to give a brownish powder (33 g) still containing some HOBT. The powder was dissolved in about 100 mL warm EtOH and water (130 mL) was added to induce a crystallisation of the25 product. The crystals was filtered off and dried to give pure tert-butyl 3-[(benzylsulfonyl)carbamoyl]azetidine-l-carboxylate as an off white powder. Yield: 25.4 g(71%).1H NMR (400 MHz, DMSO-d6) delta 1.39 (9H, s), 3.30 (IH, m, overlapping with the watersignal in DMSO), 3.78-3.95 (4H, m), 4.73 (2H, s), 7.28-7.34 (2H, m), 7.36-7.41 (3H,30 m), 11.71 (IH, br s). MS m/z: 353 (M-I).

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

Reference:
Patent; ASTRAZENECA AB; WO2008/4946; (2008); 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. 57561-39-4, name is tert-Butyl (2-hydroxyethyl)(methyl)carbamate, A new synthetic method of this compound is introduced below., Formula: C8H17NO3

(1) t-Butyl (2-hydroxyethyl)methylcarbamate (1.0 g) obtained by the method described in the literature (Synthetic Communications, 1993, p.2443) was dissolved in chloroform (5 ml), and a Dess-Martin reagent (2.54 g) was added to the solution under ice cooling. The resulting mixture was stirred at room temperature for 1.5 hours, then saturated aqueous sodium hydrogencarbonate and saturated aqueous sodium thiosulfate were added to the reaction mixture, and the resulting mixture was stirred for 30 minutes. The reaction mixture was extracted with chloroform, and the organic layer was dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure to obtain an aldehyde compound (1.21 g).

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; Taisho Pharmaceutical Co., Ltd.; Meiji Seika Kaisha, Ltd.; EP2287173; (2011); A1;,
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

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

Reference of 2895-21-8, These common heterocyclic compound, 2895-21-8, name is N-Isopropyl-2-chloroacetamide, 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.

To a solution of 2-chloro-N-isopropylacetamide (201 mg, 1.48 mmol) in ethanol (1.73 mL) was added 4-bromo-o-anisidine (300 mg, 1.48 mmol) and potassium carbonate (615 mg, 4.45 mmol). The reaction mixture was then allowed to stir at 80 C overnight. The reaction was cooled to r.t. and concentrated under reduced pressure. The residue was taken up in EtOAc, and washed with NaOH (4.0 M). The aqueous layer was extracted with EtOAc (x3), the organic layers combined, washed with saturated brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by reverse phase chromatography eluting with 30-50% acetonitrile (0.1% formic acid additive) in water (0.1% formic acid additive) to yield 2-(4-bromo-2-methoxy-anilino)-N-isopropylacetamide (110 mg, 0.36 mmol, 25% yield) as a white solid. UPLC-MS (ES+, Method A): 1.65 min, m/z 301.2 [M+H]+.1H NMR (400 MHz, CDCl3) delta6.98 (dd, J = 8.3, 2.7 Hz, 1H), 6.90 (d, J = 2.0 Hz, 1H), 6.47-6.41 (m, 1H), 6.34 (d, J = 8.3 Hz, 1H), 4.18-4.08 (m, 1H), 3.87 (s, 3H), 3.73 (s, 2H), 1.11 (d, J = 6.6 Hz, 6H).

The synthetic route of 2895-21-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; REDX PHARMA PLC; JONES, Clifford, D.; BUNYARD, Peter; PITT, Gary; BYRNE, Liam; PESNOT, Thomas; GUISOT, Nicolas, E.S.; (318 pag.)WO2019/145729; (2019); 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. 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

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

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

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