Tag: M.W=100-200

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. 431-47-0, name is Methyl 2,2,2-trifluoroacetate, A new synthetic method of this compound is introduced below., Formula: C3H3F3O2

Compound 24 (2.127 g, 3.6 mmol) was dissolved in DCM (10 g), and treated with triethylamine (0.1 mL) and methyltrifluoroacetate (0.922 g, 7.2 mmol) at 30 C. for 4 h. The reaction mixture was evaporated and purified on a silica gel column (50% hexanes/DCM?4% MeOH/DCM) to give compound 8b (1.914 g, 77.4%).

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; AM Chemicals LLC; GUZAEV, Andrei Pavel; VVEDENSKIY, Vladimir V.; GOGOI, Khirud; (90 pag.)US2018/16232; (2018); A1;,
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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. 87661-20-9, name is tert-Butyl cyclopropanecarboxylate, A new synthetic method of this compound is introduced below., HPLC of Formula: C8H14O2

To a solution of 1M LDA (42.1 mmol, 42.1 mL) at – 78 C was added dropwise t-butylcyclopropane carboxylate (5.0 g, 35.1 mmol) in 70 mL THF. After 1.5 hours, a solution of allyl bromide (3.03 mL, 35.1 mmol) in 10 mL THF was added. The reaction mixture was allowed to warm slowly to room temperature. After 18 hours, the reaction was quenched with saturated NH4CI (aq), and partitioned between EtOAc and H2O. The organic and aqueous layers were separated, and the aqueous layer was washed with 2 c 20 mL ethyl acetate. The combined organic layers were washed with brine, dried over Na2S04, filtered, and concentrated in vacuo. The residue was purified on an 80 g silacel column, eluting with 0-15% EtOAc/hexanes. The product fractions were concentrated in vacuo to yield 1-allyl-cyclopropanecarboxylic acid tert-butyl ester, 2.48 g (38% yield). 1H NMR (CHLOROFORM-d) d: 5.73-6.01 (m, 1H), 4.91-5.13 (m, 2H), 2.27 (dt, J=6.6, 1.3 Hz, 2H), 1.42 (s, 9H), 0.99-1.20 (m, 2H), 0.49-0.73 (m, 2H).

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; BIOHAVEN PHARMACEUTICAL HOLDING COMPANY LTD.; CONWAY, Charles M.; DUBOWCHIK, Gene M.; PELLETIER, Jeffery Claude; REITZ, Allen B.; (186 pag.)WO2020/77038; (2020); A1;,
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Adding a certain compound to certain chemical reactions, such as: 344-14-9, name is Dimethyl 2-fluoromalonate, belongs to esters-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 344-14-9, HPLC of Formula: C5H7FO4

General procedure: The solution of 25% NaOMe in methanol (10.28 g, 190.38 mmol) was diluted with methanol(50 ml) under N2 atm and cooled to 0 0C. To this, compound 1a (14.90 g, 95.19 mmol) followedby compound 6 (10 g, 105.77 mmol) were added and stirred the reaction mixture at roomtemperature for 16 h. The progress of the reaction was monitored by TLC (10% Ethyl acetatein petroleum ether) showed completion of the reaction. After completion of the reaction; thereaction mixture was evaporated and solid was dissolved in H2O and acidified with Conc.HCl(~ pH 2), to give the white solid. The resulting solid was filtered and washed with water anddried under vacuum give the pure compound 7a (10 g; 48.78 mmol, 72%) as an off white solid.

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, Dimethyl 2-fluoromalonate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Sambaiah; Mallesham, Poosa; Shiva Kumar; Bobde, Yamini; Hota, Prasanta Kumar; Yennam, Satyanarayana; Ghosh, Balaram; Behera, Manoranjan; Synlett; vol. 30; 5; (2019); p. 586 – 592;,
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Electric Literature of 4224-69-5, 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. 4224-69-5, name is Methyl 2-(bromomethyl)acrylate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

(2) To an anhydrous THF solution (2 ml) of the above-obtained Compound (8) (A=-CH=CH-CH=CH-, PG=TBS, 24(E)) (48 mg, 76.8 mumol) were added zinc (powder) (8 mg, 0.12 mmol), methyl 2-(bromomethyl)acrylate (13.8 mul, 0.12 mmol) and a saturated ammonium chloride aqueous solution (0.7 ml) at 0C, and the mixture was stirred for 30 min at room temperature. The reaction was quenched with water, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and then with brine, dried over anhydrous magnesium sulfate, and concentrated. The residue was purified by column chromatography (5%?20% ethyl acetate in hexane) to obtain Compound (C) (60 mg, 107% yield). Compound (C):1H NMR (CDCl3) delta : 0.055 (s, 3 H), 0.059 (s, 3 H), 0.062 (s, 6 H), 0.55 (s, 3 H), 0.88 (s, 18 H), 1.04 (d, J=6.6 Hz, 3 H), 1.23-2.17 (m, 15 H), 2.18-2.24 (m, 1 H), 2.42-2.52 (m, 2 H), 2.60-2.65 (m, 1 H), 2.78-2.86 (m, 1 H), 3.74 (s, 3 H), 4.19-4.22 (m, 1 H), 4.28-4.34 (m, 1 H), 4.34-4.39 (m, 1 H), 4.86 (d, J=2.2 Hz, 1 H), 5.17 (s, 1 H), 5.53-5.62 (m, 1 H), 5.67 (d, J=1.2 Hz, 1 H), 5.90-6.03 (m, 2 H), 6.15-6.25 (m, 2 H), 6.26 (d, J=1.2 Hz, 1 H). MS m/z 747 (M+23)+.

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, Methyl 2-(bromomethyl)acrylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; TEIJIN LIMITED; EP1477483; (2004); A1;,
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Related Products of 175278-29-2, 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. 175278-29-2, name is Methyl 5-fluoro-2-methylbenzoate, This compound has unique chemical properties. The synthetic route is as follows.

step 2: Compound 2 (19.5 g, 0.1 mol) was dissolved in 80 mL of acetic acid and 50 mL of acetic anhydride, and the temperature was lowered to 10 C. Potassium nitrate (15.2 g, 0.15 mol) was added in portions, and after the addition, the reaction was carried out for 6 h. The insoluble material was removed by filtration, and the reaction mixture was poured into 400 mL of ice water, filtered, and dried to give 17.3 g of Compound 3.

The chemical industry reduces the impact on the environment during synthesis Methyl 5-fluoro-2-methylbenzoate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Cheng Chunxiao; (7 pag.)CN108409626; (2018); A;,
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Related Products of 1234616-21-7,Some common heterocyclic compound, 1234616-21-7, name is Methyl imidazo[1,2-b]pyridazine-6-carboxylate, molecular formula is C8H7N3O2, 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.

Synthesis of imidazo[l,2-b]pyridazin-6-ylmethanol:To a stirred solution of imidazo[l,2-b]pyridazine-6-carboxylate (3.5 g, 22.77 mmol) in MeOH:THF (45 mL, 1 :2) was added NaBH4 (1.72 g, 45.26 mmol) portion wise at 0C and stirred for 2h. After full consumption of starting material by TLC, the reaction was diluted with saturated Na2C03 solution and extracted with EtOAc. The combined organic layer was dried over sodium sulphate, filtered and concentrated in vacuo to obtain the crude product. The crude material was washed with 50%> EtOAc/Hexane to afford crude imidazo[l,2-b]pyridazin-6-ylmethanol (2.5 g). 1H-NMR (DMSO-d6, 400 MHz): delta 8.21 (s, 1H), 8.06 (d, 1H), 7.21 (s, 1H), 7.24 (d, 1H), 5.68 (br s, 1H), 4.59 (s, 2H); LC-MS: 85.80%; 149.6 (M++l) (column; X-Select C-18, (50×3.0 mm, 3.5mu); RT 0.72 min. 5mM NH4OAc in water: ACN; 0.8 ml/min); TLC: 100% EtOAc (Rf: 0.2).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl imidazo[1,2-b]pyridazine-6-carboxylate, its application will become more common.

Reference:
Patent; ENVIVO PHARMACEUTICALS, INC.; RIPKA, Amy; SHAPIRO, Gideon; MCRINER, Andrew; WO2012/40230; (2012); A1;,
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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. 56741-34-5, name is Methyl 5-amino-2-fluorobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. SDS of cas: 56741-34-5

General procedure: To a solution of 11a (500 mg, 1.85 mmol) in acetone (10 mL) was added 12 (380 mg, 1.85 mmol) and pyridine (0.45 mL, 5.54 mmol).The mixture was stirred at 55 C for 1 h. The mixture was concentrated,diluted with ethyl acetate and washed with 1M HCl and brine twice.Then, the ethyl acetate layer was dried over anhydrous sodium sulfate andconcentrated to give the crude product. The crude product was purified bysilica column eluting with petroleum ether/ethyl acetate (5/1-2/1) to givethe desired product (0.33 g, yield 44.3%) as grey solid

The synthetic route of 56741-34-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; He, Yulong; Dou, Huixia; Gao, Dingding; Wang, Ting; Zhang, Mingming; Wang, Heyao; Li, Yingxia; Bioorganic and Medicinal Chemistry; vol. 27; 19; (2019);,
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Electric Literature of 35179-98-7, 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. 35179-98-7, name is Chloromethyl ethyl carbonate, This compound has unique chemical properties. The synthetic route is as follows.

To DMF (10 mL) were added chloromethyl ethyl carbonate (0.66 g, 4.77 mmol),potassium carbonate (1.00 g, 7.16 mmol) and (2S,3S)-3-((2-bromo-6-(5-chlorothiophen-2-yl)-5-fluoropyrimidin-4-yl)amino)bicyclo[2.2.2]octane-2-carboxylic acid (1.10 g, 2.39 mmol) andthe mixture was stirred at rt overnight. To the reaction mixture was added water (40 mL), and theresulting mixture was extracted with ethyl acetate (30 mL x 3). The combined organic layerswere washed with saturated brine (30 mL), dried over anhydrous sodium sulfate and filtered. Thefiltrate was concentrated and the residue was purified by silica gel column chromatography(PE/EtOAc (v/v) = 1511) to give the title compound as a light yellow solid (0.90 g, 67 %).

The chemical industry reduces the impact on the environment during synthesis Chloromethyl ethyl carbonate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; TANG, Changhua; REN, Qingyun; YIN, Junjun; YI, Kai; LEI, Yibo; WANG, Yejun; ZHANG, Yingjun; (303 pag.)WO2018/108125; (2018); A1;,
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2318-25-4, 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. 2318-25-4, name is Ethyl 3-ethoxy-3-iminopropionate hydrochloride belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A 5000 ml_, 4-neck flask was fitted with a stirrer, thermometer, condenser, and gas inlet/outlet. The equipped flask was charged with 265.7 g (1.12 mol. 1.0 eq) of 5-(4-methyl-piperazin-1-yl)-2-nitroaniline and 2125 ml_ of 200 proof EtOH. The resulting solution was purged with N2 for 15 minutes. Next, 20.0 g of 5percent Pd/C (50percent H2O w/w) was added. The reaction was vigorously stirred at 40-500C (internal temperature) while H2 was bubbled through the mixture. The reaction was monitored hourly for the disappearance of 5-(4- methyl-piperazin-1-yl)-2-nitroaniline by HPLC. The typical reaction time was 6 hours.[0091] 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 HCI 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 H2O (2 x 400 mL) and dried at 50°C in a vacuum oven providing 251.7 g (74.1 percent) of [6-(4-methyl-piperazin-1-yl)- 1 H-benzoimidazol-2-yl]-acetic acid ethyl ester as a pale yellow powder.; A 5000 mL, 4-neck jacketed flask was fitted with a mechanical stirrer, condenser, temperature probe, gas inlet, and oil bubbler. The equipped flask was charged with 300 g (1.27 mol) of 5-(4-methyl-piperazin-1-yl)-2- nitroaniline and 2400 mL of 200 proof EtOH (the reaction may be and has been conducted with 95percent ethanol and it is not necessary to use 200 proof ethanol for this reaction). The resulting solution was stirred and purged with N2 for 15 minutes. Next, 22.7 g of 5percent Pd/C (50percent H2O w/w) was added to the reaction flask. The reaction vessel was purged with N2 for 15 minutes. After purging with N2, the reaction vessel was purged with H2 by maintaining a slow, but constant flow of H2 through the flask. The reaction was stirred at 45-55°C (internal temperature) while H2 was bubbled through the mixture until the 5-(4-methyl- piperazin-1-yl)-2-nitroaniline was completely consumed as determined by HPLC. The typical reaction time was 6 hours.[0093] 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 45-550C (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 1 M 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 20-250C. The resulting mixture was filtered, and the filter cake was washed with H2O (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)-1 H- 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.

The synthetic route of Ethyl 3-ethoxy-3-iminopropionate hydrochloride has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; WO2008/112509; (2008); A1;,
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Synthetic Route of 1128-00-3, A common heterocyclic compound, 1128-00-3, name is Ethyl 2-aminocyclohex-1-enecarboxylate, molecular formula is C9H15NO2, 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 ethyl 2-aminocyclohex-1-enecarboxylate (33) (3.33 g, 19.7 mmol) and pyridine (2.33 g, 29.5 mmol) in dry THF (50 ml) at -5 C slowly within 1 h 2-bromoacetyl bromide (3.93 g, 19.5 mmol) was added. The reaction mixture was stirred at the same temperature for 45 min. and partitioned between ethyl acetate (50 ml) and satd NaHCO3 (50 ml). The water phase was extracted with ethyl acetate (3 × 30 ml). The organic extracts were combined, and successively washed with satd NaHCO3 solution (50 ml), water (2 × 50 ml), satd NaCl solution (50 ml), and dried (Na2SO4). The solvent was evaporated, the residue was mixed with ethyl acetate (50 ml), and the solid material was filtered off. The filtrate was evaporated to dryness and the residue was dried in vacuo over P2O5 to give 5.00 g (88%) of compound 34 as a brown oil, which was immediately utilized in the next step. 1H NMR (CDCl3) delta: 1.30 (t, J = 7.1 Hz, 3H), 1.55-1.68 (m, 4H), 2.30-2.36 (m, 2H), 2.90-2.96 (m, 2H), 3.86 (s, 2H), 4.21 (q, J = 7.1 Hz, 2H), 12.08 (br s, 1H). GCMS m/z: 289.0 M+.

The synthetic route of 1128-00-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Bobileva, Olga; Bokaldere, Rasma; Gailite, Vija; Kaula, Ilze; Ikaunieks, Martins; Duburs, Gunars; Petrovska, Ramona; Mandrika, Ilona; Klovins, Janis; Loza, Einars; Bioorganic and Medicinal Chemistry; vol. 22; 14; (2014); p. 3654 – 3669;,
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