Month: August 2021

Synthetic Route of 24036-52-0, These common heterocyclic compound, 24036-52-0, name is 6-Bromo-2H-1,4-benzoxazin-3(4H)-one, 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.

Step A; A degassed suspension of commercially available 6-Bromo-4H- benzo[l,4]oxazin-3-one (8.39 g), Zn(CN)2 (3.46 g) and Pd(PPh3)4 (2.13 g) in DMF (70 mL) was stirred in a oil bath (80 C) overnight. The mixture was cooled to room temperature and then poured into water (500 mL). The precipitate was collected by suction, air dried, washed with pentane, dissolved in CH2Cl2ZMeOH (1:1), filtered through an silica pad and concentrated to yield a yellow solid (5.68 ^ 89 0ZoJ MH+ = ITS).

Statistics shows that 6-Bromo-2H-1,4-benzoxazin-3(4H)-one is playing an increasingly important role. we look forward to future research findings about 24036-52-0.

Reference:
Patent; ALANTOS PHARMACEUTICALS HOLDING, INC.; WO2008/63669; (2008); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

These common heterocyclic compound, 154350-29-5, name is Cyclopropanesulfonamide, 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 Cyclopropanesulfonamide

14-tert-Butoxycarbonylamino- 18-(tert-butyl-dimethyl-silanyloxy)-2, 15-dioxo-3, 16- diaza-tricyclo[14.3.0.04’6]nonadec-7-ene-4-carboxylic acid (500 mg, 0.86 mmoL) was dissolved in 25 mL of THF and treated with CDI (180 mg, 1.12 mmoL). (Care was taken to avoid moisture by using oven dried glassware and maintaining a dry N2 atmosphere). After refluxing the reaction mixture for 2 h, it was cooled to rt and treated sequentially with cyclopropylsulfonamide (135 mg, 1.12 mmoL) and DBU (170 mg, 1.12 mmoL). The reaction mixture was stirred for 4 h at rt, and the THF was removed by rotary evaporation. The residue was partitioned between ethyl acetate and pH 4 buffer. The organic phase was dried (MgSO4) and concentrated in vacuo to give the crude product. It was then purified by flash chromatography (eluting with 33percent ethyl acetate in hexane) to give 300 mg (51percent) of [ 18-(tert-butyl- dimethyl-silanyloxy)-4-cyclopropanesulfonylaminocarbonyl-2,15-dioxo-3,16-diaza- tricyclo[14.3.0.04’6]nonadec-7-en-14-yl]-carbamic acid tert-butyl ester as a white solid. 1H NMR (300 MHz, CD3OD) delta IH 0.07 (s, 3 H), 0.08 (s, 3 H), 0.85 (s, 9 H), 0.87-1.49 (m, 21 H), 1.73-1.95 (m, 3 H), 2.08-2.16 (m, 1 H), 2.25-2.36 (m, 2 H), 2.42-2.56 (m, 1 H), 2.85-2.93 (m, 1 H), 3.65-3.74(dd, ./=10.61, 3.66 Hz, 1 H), 3.89 (d, J=10.25 Hz, 1 H), 4.34 (m, J=9.70, 9.70 Hz, 1 H), 4.43 (t, J=7.87 Hz, 1 H), 4.57 (s, 1 H), 4.94-5.01 (m, 1 H), 5.10 (d, J=8.78 Hz, 1 H), 5.66-5.75 (m, 1 H), 6.55 (s, 1 H), 10.13 (s, 1 H); MS m/z 683 (M++l).

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

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2008/64057; (2008); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 94838-59-2, 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. 94838-59-2, name is tert-Butyl 4-aminophenethylcarbamate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Compound 31: Add 30 (1.0 mmol) drop-wise to a solution of 29 (1.0 mmol) and NEt3 (2.0 mmol) in THF 10.0 mL under nitrogen at 0 C. When the reaction is completed, dilute with ethyl acetate. Wash with 1.0 M HCl, aqueous sat. NaHCO3, and brine. Dry with Na2SO4, concentrate, and purify by flash column chromatography to obtain 31.

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 4-aminophenethylcarbamate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Sunesis Pharmaceuticals, Inc.; US2007/27166; (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. 96-30-0, name is 2-Chloro-N-methylacetamide, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 96-30-0

Step B 2-[[2-(3-Benzyloxy-phenyl)-ethyl]-(cyclopropylmethyl)amino]-N-methyl-acetamide hydrochloride; A mixture of 0.24 g (0.85 mmol) of [2-(3-benzyloxy-phenyl)-ethyl]- (cyclopropylmethyl)amine, 0.14 ml (1.00 mmol) of triethylamine, 0.11 g (1.02 mmol) of 2- chloro-N-methyl-acetamide in 3 ml of dimethylformamide was heated with microwaves to 120 0C for 2 hours. The solvent was removed and the crude residue was purified by flash chromatography (dichloromethane/methanol/Ntb 100:0:0 -? 95:5:0.5 gradient). The product obtained was dissolved in anhydrous hydrochloric acid in ethyl acetate, the solvent was removed under vacuum and the residue was triturated with diethyl ether. 0.24 g (80% yield) of the title compound was isolated as a yellow solid.1H-NMR CDCl3: 7.47-6.68 (m, 9H); 5.06 (s, 2H); 3.15 (s, 2H); 2.86-2.62 (m, 4H); 2.56 (d, 3H); 2.43 (d, 2H); 0.92 -0.67 (m, IH); 0.59 -0.44 (m, 2H); 0.16 -0.04 (m, 2H) LC-MS: MH+ = 353

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 96-30-0.

Reference:
Patent; NEWRON PHARMACEUTICALS S.P.A.; WO2007/71311; (2007); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Related Products of 2603-10-3, 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 2603-10-3 as follows.

7.5 g methyl phenyl carbamate (MPC) was added to 50 mL single-necked flask, 20 mL of dimethyl carbonate was added, heated at 60 and dissolved. 10 mL of concentrated hydrochloric acid (37% w / w) was added, 10mL formaldehyde solution (mass concentration of 36%), was added and reacted for two hours. After the reaction was completed, the solid was filtered, the filtrate was analyzed by high performance liquid chromatography, the contents of phenyl carbamate and diphenylmethane dicarbamate (MDC) were determined. The solid was washed three times with 50 ml of water, vacuum dried at 80 for 48h. A small amount of solid samples were taken and content and purity of diphenylmethane dicarbamate were determined. Analysis results showed that MPC conversion was 99%, MDC yield was 97% and selectivity was 98%.

According to the analysis of related databases, 2603-10-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Sinopec Corporation; Nan Hua Group Institute; Ding Hongxia; Jin Yucun; Jin Hanqiang; Wu Qijian; Chen Yongping; Liu Zhuo; He Yumiao; (7 pag.)CN107434774; (2017); A;,
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. 143557-91-9, name is tert-Butyl 3-endo-3-hydroxy-8-azabicyclo[3.2.1]octane-8-carboxylate, A new synthetic method of this compound is introduced below., Safety of tert-Butyl 3-endo-3-hydroxy-8-azabicyclo[3.2.1]octane-8-carboxylate

General procedure: . Following GP1, under N2 atmosphere, to a 0C. solution of tert-butyl (1R,3r,5S)-3-hydroxybicyclo[3.2.1]octane-8-carboxylate (0.15 g, 1 eq., 0.66 mmol), phenol (0.07 g, 1.2 eq., 0.79 mmol), and PPh3 (0.21 mg, 1.5 eq., 0.99 mmol) in dry THF (5 mL) was added dropwise diisopropyl azodicarboxylate (0.2 mL, 1.2 eq., 0.79 mmol). The reaction crude was allowed to warm to room temperature and stirred for 16 h. Then, the mixture was quenched with HCl (10 mL) and extracted with EtOAc (25 mL). The organic extracts were washed with brine (10 mL), dried over Na2SO4 and concentrated in vacuo to furnish the crude product, which was purified by flash chromatography eluting with cyclohexane/EtOAc (0 to 80%) to give the pure title compound as colourless oil (0.07 g, 40%). UPLC-MS (method A): Rt. 1.86 min (TIC); ionization ES+304 [M+H]+. 1H NMR (400 MHz, DMSO-d6): delta 7.30-7.23 (m, 2H), 7.01-6.95 (m, 2H), 6.92 (td, J=7.3, 1.1Hz, 1H), 4.85-4.74 (m, 1H), 4.19-4.10 (m, 2H), 2.15-2.03 (m, 2H), 1.95-1.73 (m, 4H), 1.58-1.46 (m, 2H), 1.42 (s, 9H), 1.40-1.37 (m, 1H).

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; FONDAZIONE ISTITUTO ITALIANO DI TECNOLOGIA; BERTOZZI, Fabio; BANDIERA, Tiziano; PONTIS, Silvia; REGGIANI, Angelo; GIACOMINA, Francesca; DI FRUSCIA, Paolo; US2019/135778; (2019); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Some common heterocyclic compound, 1386861-46-6, name is 2-Chloro-6-methyl-N-phenylbenzamide, molecular formula is C14H12ClNO, 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. COA of Formula: C14H12ClNO

General procedure: 00685] To a stirred mixture of amide (E-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.[00686] To a stirred mixture of (S)-tert-butyl l-(methoxy(methyl)amino)-l-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 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. HC1 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. HC1 (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 MgSC>4 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, white solid precipitates out 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-(l -aminoethyl)-isoquinolin- 1 (2H)-ones (E-3).Amine 1-1 was prepared according to Method E and then coupled to (A-3) using Method I to provide compound 1-2. ESI-MS m/z: 428.0 [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 1386861-46-6, its application will become more common.

Reference:
Patent; INFINITY PHARMACEUTICALS INC.; INTELLIKINE, LLC; CASTRO, Alfredo, C.; EVANS, Catherine, A.; JANARDANANNAIR, Somarajannair; LESCARBEAU, Andre; LIU, Tao; SNYDER, Daniel, A.; TREMBLAY, Martin, R.; REN, Pingda; LIU, Yi; LI, Liansheng; CHAN, Katrina; WO2013/12915; (2013); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 337463-88-4, 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 337463-88-4 as follows.

The bromopyridine (h) (6.0 g, 26.3 mmol) and trans-2-phenylvinylboronic acid (3.9 g, 26.3 mmol) were dissolved in 1,4-dioxane (150 ml) and the solution was degassed with argon. (Ph3P) 4Pd (230 mg, 0.2 mmol) was added, followed by a solution of potassium carbonate (6.9 g, 50 mmol) in water (20 ml). The reaction was heated at reflux under argon overnight, then was cooled to room temperature and diluted with EtOAc (200 ml). The solution was washed sequentially with water and brine, dried (Na2S04), and concentrated in vacuo. The solid residue was purified by flash chromatography on silica gel (5-10% EtOAc/CHC13) to afford a solid (2. 5g, 38%). MS (+ve ion electrospray) m/z 253 (MH+).

According to the analysis of related databases, 337463-88-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXO GROUP LIMITED; WO2004/2490; (2004); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Related Products of 7160-22-7, These common heterocyclic compound, 7160-22-7, name is N-(3,4-Dichlorophenyl)pivalamide, 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.

2b) Preparation of Compound 2; A solution of Compound 1 (50 g) in tetrahydrofuran (300 mL) was cooled to-50 – -4O0C under an inert atmosphere of nitrogen. N-Butyl lithium (2.5M in hexanes, 179 mL) was added at such a rate as to keep the solution’s internal temperature between -45 – -30 0C (ca. 15 – 30 min addition). The solution was held at ca. -35 – -25 0C until HPLC indicated that the initial reaction was complete. The solution was then recooled to – 45 – 4O0C, and sulfur dioxide (-16.9 g) was bubbled through the solution, keeping the internal temperature below approximately -14 0C, until the solution was acidic. When the reaction was complete, the mixture was warmed to -10 – 0 0C. Starting at -2 – 3 0C, sulfuryl chloride (25.2 mL) was then added dropwise to the tetrahydrofuran solution over 5 – 15 min, keeping the temperature below approximately 22 0C. After 5 min, HPLC confirmed reaction completion, while the solution was kept around 10 – 15 0C. The mixture was solvent-exchanged into alpha,alpha,alpha-trifluorotoluene under reduced pressure, filtered, partially concentrated under vacuum (to -100 mL), followed by addition of dichloromethane (350 mL). To this mixture was added a solution of piperazine (61.2 g) in dichloromethane (625 mL) at ambient temperature dropwise, keeping the solution’s internal temperature at 15 – 27 0C (2h addition). The reaction was held at 20 – 24 0C until complete. The mixture was washed with deionized water (200 mL), the organic layer concentrated, followed by addition of heptane (450 mL). The product (70.5 g) was isolated by filtration, washed with heptane (50-100 mL), and dried under vacuum at 50-55 0C.

The synthetic route of 7160-22-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2009/39091; (2009); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

These common heterocyclic compound, 77925-80-5, name is N-(Benzyloxy)-2-nitrobenzenesulfonamide, 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. Application In Synthesis of N-(Benzyloxy)-2-nitrobenzenesulfonamide

To a solution of fe/ -butyl (3S,4aS,7aS)-6-allyl-3-hydroxy-7-oxooctahydro-1 H-pyrrolo[3,4- b]pyridine-1 -carboxylate (786.4 mg, 2.65 mmol), /V-(benzyloxy)-2-nitrobenzenesulfonamide (900 mg, 2.92 mmol) and triphenylphosphine (835 mg, 3.18 mmol) in THF (29 mL) at -17 C was added DIAD (0.640 mL, 3.18 mmol) as a soln in THF (4.1 mL) drop-wise at 6:30 pm. It was allowed to slowly warm to rt and stir for 22 h then concentrated in vacuo and purified directly via silica gel chromatography (EtOAc-heptane, 0-40%), affording the title compound (846 mg, 54%) as an off-white solid. LCMS: Rt = 0.95 min; m/z = 587.3 (M+1 ) Method 2m acidic.

The synthetic route of N-(Benzyloxy)-2-nitrobenzenesulfonamide has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; CASAREZ, Anthony; FUREGATI, Markus; KOCH, Guido; LIN, Xiaodong; OSSOLA, Flavio; RECK, Folkert; SIMMONS, Robert Lowell; ZHU, Qingming; (113 pag.)WO2018/60926; (2018); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics