Month: July 2021

Application of 36692-49-6, A common heterocyclic compound, 36692-49-6, name is Methyl 3,4-diaminobenzoate, molecular formula is C8H10N2O2, 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.

General procedure: A 25 mL sealed tube equipped with a magnetic stirrer bar was charged with catalyst CoOxNC-800 (20 mg, 10 mol%) then sealed with a rubber septum and evacuated to remove air.Benzene-1,2-diamine (0.2 mmol), PhCHO (0.24 mmol), and THF(5 mL) were injected into the tube from a syringe, and the tube was placed in a preheated oil bath at 100 C for 8 h. When the reaction was complete, the mixture was filtered and the organic layers were collected, combined, dried (Na2SO4), and concentrated under vacuum. The residue was purified by passage through a column of silica gel (200-300 mesh) to give a white solid; yield: 38.1 mg (98%).

The synthetic route of 36692-49-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wang, Zhaozhan; Song, Tao; Yang, Yong; Synlett; vol. 30; 3; (2019); p. 319 – 324;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 2318-25-4, 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. 2318-25-4 name is Ethyl 3-ethoxy-3-iminopropionate hydrochloride, 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.

After all the 5- (4-methyl-piperazin-1-yl)-2-nitroaniline had disappeared from the reaction, the solution was purged with N2 for 15 minutes. Next, 440.0 g (2.25 mol) of ethyl 3-ethoxy-3-iminopropanoate hydrochloride was added as a solid. The reaction was stirred at 40-50°C (internal temperature) until the reaction was complete. The reaction was monitored by following the disappearance of the diamino compound by HPLC. The typical reaction time was 1-2 hours. After the reaction was complete, it was cooled to room temperature and filtered through a pad of Celite filtering material. The Celite filtering material was washed with absolute EtOH (2 x 250 mL), and the filtrate was concentrated under reduced pressure providing a thick brown/orange oil. The resulting oil was taken up in 850 mL of a 0.37percent HC1 solution. Solid NaOH (25 g) was then added in one portion, and a precipitate formed. The resulting mixture was stirred for 1 hour and then filtered. The solid was washed with H20 (2 x 400 mL) and dried at 50°C in a vacuum oven providing 251.7 g (74.1percent) of [6- (4-methyl-piperazin-1-yl)-lH-benzoimidazol-2-yl]- acetic acid ethyl ester as a pale yellow powder.After all the 5- (4-methyl-piperazin-1-yl)-2-nitroaniline had disappeared from the reaction, the solution was purged with N2 for 15 minutes. The diamine intermediate is air sensitive so care was taken to avoid exposure to air. 500 g (2.56 mol) of ethyl 3-ethoxy-3-iminopropanoate hydrochloride was added to the reaction mixture over a period of about 30 minutes. The reaction was stirred at 45- 55°C (internal temperature) under N2 until the diamine was completely consumed as determined by HPLC. The typical reaction time was about 2 hours. After the reaction was complete, the reaction was filtered while warm through a pad of Celite. The reaction flask and Celite were then washed with 200 proof EtOH (3 x 285 mL). The filtrates were combined in a 5000 mL flask, and about 3300 mL of ethanol was removed under vacuum producing an orange oil. Water (530 mL) and then 1M HCL (350 mL) were added to the resulting oil, and the resulting mixture was stirred. The resulting solution was vigorously stirred while 30percent NaOH (200 mL) was added over a period of about 20 minutes maintaining the internal temperature at about 25-30°C while the pH was brought to between 9 and 10. The resulting suspension was stirred for about 4 hours while maintaining the internal temperature at about 20-25°C. The resulting mixture was filtered, and the filter cake was washed with H20 (3 x 300 mL). The collected solid was dried to a constant weight at 50°C under vacuum in a vacuum oven providing 345.9 g (90. 1percent) of [6- (4-methyl-piperazin-1-yl)-lH-benzoimidazol-2- yl] -acetic acid ethyl ester as a pale yellow powder. In an alternative work up procedure, the filtrates were combined and the ethanol was removed under vacuum until at least about 90percent had been removed. Water at a neutral pH was then added to the resulting oil, and the solution was cooled to about 0°C. An aqueous 20percent NaOH solution was then added slowly with rapid stirring to bring the pH up to 9.2 (read with pH meter). The resulting mixture was then filtered and dried as described above. The alternative work up procedure provided the light tan to light yellow product in yields as high as 97percent.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Ethyl 3-ethoxy-3-iminopropionate hydrochloride, and friends who are interested can also refer to it.

Reference:
Patent; CHIRON CORPORATION; WO2005/82340; (2005); A2;,
Ester – Wikipedia,
Ester – 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. 54535-22-7, name is Diethyl 2-((phenylamino)methylene)malonate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Product Details of 54535-22-7

Step b :4-hydroxyquinoline 3- carboxylic acid ethyl ester A clean and dry I liter round bottom flask, fitted with mechanical stirrer and thermo pocket was charged 2-Phenylaminotnethylene malonic acid diethyl ester (100 g) and Eaton’s reagent (400 ml) at room temperature. The reaction mass was heated to 80-90 C. and maintained under stirring for 4-6 hours at the same temperature. After completion, the reaction mass was cooled to 5-10 C. and was treated with aqueous sodium carbonate solution at 0-10 C. and stirred for 60-90 minutes at the same temperature. The resultant solid was filtered, washed with water (until the water filtrate showed neutral pH) and dried at 45-50 for 6-8 hours to obtain 4-hydroxyquinoline 3-carboxylic acid ethyl ester (70-80 g)

The synthetic route of 54535-22-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Optimus Drugs Private Limited; Desi Reddy, Srinivas Reddy; Rane, Dnyandev Ragho; Velivela, Venkata Srinivasa Rao; (11 pag.)US2017/96397; (2017); A1;,
Ester – Wikipedia,
Ester – 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. 27492-84-8, name is Methyl 4-amino-2-methoxybenzoate, A new synthetic method of this compound is introduced below., HPLC of Formula: C9H11NO3

Step 1Methyl 2-methoxy-4-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamido)benzoateProcedure:A mixture of 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid (600 mg, 2.4 mmol), methyl 4-amino-2-methoxybenzoate (362 mg, 2 mmol), EDCI (764 mg, 4 mmol) and DMAP (488 mg, 4 mmol) in 10 mL of DMF was stirred at room temperature for 38 hours.The mixture was poured into water and extracted with EtOAc (3*15 mL).The organic layer was washed with brine and dried over Na2SO4.After filtration and concentration, the residue was purified by column chromatography on silica gel eluting with (petroleum ether_EtOAc=4:1) to give methyl 2-methoxy-4-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamido)benzoate (180 mg, 22percent) as solid. 1H NMR (300 MHz, CD3OD): delta 8.31 (s, 1H), 8.05-8.01 (m, 1H), 7.97-7.94 (m, 1H), 7.81 (d, 1H, J=8.7 Hz), 7.71 (d, 1H, J=1.8 Hz), 7.53 (d, 1H, J=7.5 Hz), 7.37 (dd, 1H, J1=8.7 Hz, J2=2.1 Hz), 3.91 (s, 3H), 3.85 (s, 3H).

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; Hermann, Johannes Cornelius; Lowrie, JR., Lee Edwin; Lucas, Matthew C.; Luk, Kin-Chun Thomas; Padilla, Fernando; Wanner, Jutta; Xie, Wenwei; Zhang, Xiaohu; US2012/252777; (2012); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 924-99-2,Some common heterocyclic compound, 924-99-2, name is Ethyl 3-(dimethylamino)acrylate, molecular formula is C7H13NO2, 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 2; N-[(2E)-1-(Chlorofluoromethyl)-3-(dimethylamino)-2-(ethoxycarbonyl)-prop-2-en-1-ylidene]-N-methyl-methanaminium tetrafluoroborate; 17.6 g (0.1 mmol) of N-1,1,2-trifluoro-2-chloroethyldimethylamine were initially charged in 100 ml of dichloromethane under argon and admixed at RT with 13.6 g (0.1 mol) of boron trifluoride-diethyl ether complex. After stirring for 30 min, 14.3 g (0.1 mol) of ethyl dimethylaminoacrylate were added and the mixture was stirred at RT for 2 h. After the dichloromethane had been removed under reduced pressure, 25.2 g (95% of theory) of the product were obtained.

The synthetic route of 924-99-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bayer CropScience AG; US2009/326242; (2009); A1;,
Ester – Wikipedia,
Ester – 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. 924-99-2, name is Ethyl 3-(dimethylamino)acrylate, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of Ethyl 3-(dimethylamino)acrylate

[1353] to a mixture of ethyl 3-(dimethylamino)acrylate (92 mg, 639 umol), tea (129 mg, 1.28 mmol) in THF (10 ml) was added a solution of compound 288b (200 mg, 1.28 mmol) in THF (10 ml) over a period of 20 min. The mixture was stirred at 20 C and stirred for 12 hours. The reaction mixture was concentrated. The residue was purified by preparatory- tlc (SiO2, petroleum ether: ethyl acetate = 1 : 1) to give compound 288c (150 mg, yield: 53.8%) as yellow oil. 1H NMR (400mhz, CDCl3) delta 9.02 – 8.97 (m, 1h), 8.75 (d, = 4.6 hz, 1h), 7.87 – 7.76 (m, 2h), 7.45 – 7.36 (m, 1h), 4.27 (q, j = 7.3 hz, 2h), 1.26 (t, j = 7.2 hz, 3h).

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 924-99-2.

Reference:
Patent; BLADE THERAPEUTICS, INC.; BUCKMAN, Brad, Owen; YUAN, Shendong; ADLER, Marc; EMAYAN, Kumaraswamy; MA, Jingyuang; (687 pag.)WO2018/64119; (2018); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

69812-51-7, name is Methyl 4-chlorosulfonylbenzoate, belongs to esters-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Recommanded Product: Methyl 4-chlorosulfonylbenzoate

Example 5-35a Methyl 4-(N-(4-methoxyphenyl)sulfamoyl)benzoate To 4-methoxybenzenamine (580 mg, 4.71 mmol) and triethylamine (1.48 mL, 10.7 mmol) in dichloromethane (10 mL) was added methyl 4-(chlorosulfonyl)benzoate (1.00 g, 4.28 mmol). This mixture was stirred for 16 hours at room temperature. The reaction was diluted with dichloromethane (50 mL) and washed consecutively with water, 10% citric acid, and brine. The organics were dried over sodium sulfate and concentrated via rotovap. The resulting crude material was chromatographed on silica gel using 100% dichloromethane as eluent affording Methyl 4-(N-(4-methoxyphenyl)sulfamoyl)benzoate as a white crystalline solid (400 mg, 30% yield)

The synthetic route of 69812-51-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Senomyx, Inc.; US2009/274632; (2009); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 55666-43-8,Some common heterocyclic compound, 55666-43-8, name is tert-Butyl 3-bromopropanoate, molecular formula is C7H13BrO2, 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 No.16: Preparation of tert-butyl 3,3′-(4-(3-(3-chloro-4-isopropoxyphenyl)-l,2,4- oxadiazol-5-yl)phenylsulfonylazanediyl)dipropanoate and tert-butyl 3-(4-(3-(3-chloro-4- isopropoxyphenyl)-l,2,4-oxadiazol-5-yl)phenylsuIfonamido)propanoate; To a solution of 4-(3-(3-chloro-4-isopropoxyphenyI)-l,2,4-oxadiazol-5- yl)benzenesulfonamide (0.500 g, 1.270 mmol) in DMF (3.17 ml) was added NaH (0.056 g, 1.396 mmol). After about 10 min. tert-butyl 3-bromopropanoate (0.233 ml, 1.396 mmol) was added and the reaction mixture was heated to about 600C. After about 48h the reaction mixture was cooled to room temperature and purified by chromatography on silica gel (eluting with EtO Ac/Hep) to provide tert-butyl 3,3′-(4-(3-(3-chloro-4-isopropoxyphenyl)-l,2,4- oxadiazol-5-yl)phenylsulfonylazanediyl)dipropanoate (0.24 g, 29%) as a colorless solid. LCMS (Table 1, Method c) R, = 3.43 min, m/z 667 (M+NH»)+. In addition to tert-butyl 3-(4- (3-(3-chloro-4-isopropoxyphenyl)-l,2,4-oxadiazol-5-yl)phenylsulfonamido)propanoate (0.28 g, 42%) as a colorless solid. LCMS (Table 1, Method c) R1 = 3.13 min, m/z 521 (M-H)’.

The synthetic route of 55666-43-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ABBOTT LABORATORIES; WO2008/76356; (2008); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 6232-12-8, 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. 6232-12-8, name is Ethyl 4-(aminomethyl)benzoate hydrochloride belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Reference Example 178 ethyl 5-{[({4-[(ethyloxy)carbonyl]phenyl}methyl)amino]carbonyl}-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidine-2-carboxylate (2089) (2090) To a mixture of 2-[(ethyloxy)carbonyl]-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidine-5-carboxylic acid (600 mg, 2.24 mmol) obtained in Reference Example 176 and THP (6 mL) were added oxalyl chloride (0.590 mL, 6.72 mmol) and DMF (0.0500 mL, 0.650 mmol) and the mixture was stirred at room temperature for 1 hr. The reaction mixture was concentrated under reduced pressure. To a suspension of the concentrated residue in THF (6 mL) were added ethyl 4-(aminomethyl)benzoate hydrochloride (966 mg, 4.48 mmol) and triethylamine (1.20 mL, 8.96 mmol), and the mixture was stirred at room temperature for 12 hrs. The reaction mixture was concentrated under reduced pressure and ethyl acetate was added to the obtained residue. The organic layer was washed with 1N hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution, 1N hydrochloric acid and saturated brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The concentrated residue was crystallized from ethyl acetate to give the title compound as a white powder (771 mg, 80%). (2091) melting point: 227-228 C. (2092) 1H NMR (300 MHz, DMSO-d6) delta 1.31 (3H, t, J=6.2 Hz), 1.36 (3H, t, J=6.2 Hz), 4.31 (2H, q, J=7.1 Hz), 4.40 (2H, q, J=7.1 Hz), 4.65 (2H, d, J=5.5 Hz), 7.50 (2H, d, J=8.5 Hz), 7.93 (2H, d, J=8.5 Hz), 8.57 (1H, s), 11.27 (1H, s), 13.53 (1H, s).

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, Ethyl 4-(aminomethyl)benzoate hydrochloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Takeda Pharmaceutical Company Limited; Terauchi, Jun; Nara, Hiroshi; Oki, Hideyuki; Sato, Kenjiro; (166 pag.)US2015/329556; (2015); A1;,
Ester – Wikipedia,
Ester – 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. 178312-47-5, name is Ethyl 4,4-difluorocyclohexanecarboxylate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. COA of Formula: C9H14F2O2

To a stirring solution of crude compound 2 (2.8 g, 14.5 mmol) in THF (50 mL) was added LiHMDS (1M in THF) (21.8 mL, 21.8 mmol) at -78 C and stirred for 1 h. To this, BOM- chloride (2.42 mL, 17.4 mmol) was added drop wise at -78 C; warmed to RT and stirred at RT for 4 h. After consumption of the starting material (by TLC), the reaction was quenched with NH4Cl solution (50 mL) and extracted with EtOAc (2 x 100 mL). The combined organic layer dried over Na2SO4 and concentrated to obtain compound 3 (2.5 g, 55%) as colorless liquid. 1H NMR (500 MHz, CDCl3) delta 7.40-7.21 (m, 5H), 4.49 (s, 2H), 4.22-4.09 (m, 2H), 3.52 (s, 1H), 3.45 (s, 1H), 2.33-2.21 (m, 2H), 2.19-1.93 (m, 2H), 1.93-1.77 (m, 2H), 1.63-1.51 (m, 2H), 1.27 (t, J = 7.1 Hz, 3H). (0435) LCMS (m/z): 313.2 [M++1]

The synthetic route of 178312-47-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; APTINYX INC.; KHAN, M, Amin; (134 pag.)WO2018/26763; (2018); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics