Tag: M.W=100-200

Electric Literature of 23426-63-3,Some common heterocyclic compound, 23426-63-3, name is Methyl 2-bromo-2-methylpropanoate, molecular formula is C5H9BrO2, 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 B; 2,5-Dimethyl-4-thiocyanato-phenol 82 (5.75 g, 32.1 mmol) is dissolved in acetonitrile (25 mL) . Powdered cesium carbonate (15.32 g, 47.0 mmol) is added. Then 2-bromo-2- methyl-propionic acid methyl ester (4.50 mL, 34.8 mmol) is added and the mixture is stirred at 600C for 18 h. Filtration and concentration, followed by silica gel chromatography (0- 50% ethyl acetate in hexanes) yielded 2- (2, 5-dimethyl-4- thiocyanato-phenoxy) -2-methyl-propionic acid methyl ester 83 as an oil: 1H-NMR (400 MHz, CDCl3) (rotamers are present; the data given is for the most abundant isomer) delta = 7.39 (s, IH), 6.50 (S, IH), 3.78 (s, 3H)7 2.42 (s, 3H), 2.20 (s, 3H), 1.62 (s, 6H). MS calcd. for C14H17NNaO3S (M+Na+) 302.1, found 302.1.

The synthetic route of 23426-63-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; IRM LLC; WO2007/56366; (2007); A2;,
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These common heterocyclic compound, 426-65-3, name is Ethyl Pentafluoropropionate, 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. 426-65-3

General procedure: Sodium hydride (4.0 g, 100 mmol, 60% dispersion in mineral oil) was placed in a 500mL round-bottom flack and 50 mL of dry hexane was added. The suspension was stirred for a short time with a magnetic stirring bar and kept until the hexane layer became clear (20-30 min). Hexane was cautiously removed with a glass pipette until a wet paste of NaH remained. This procedure was repeated twice. After that, THF (150mL) was added with vigorous stirring. Anhydrous EtOH (0.5 mL) was added in oneportion at 0 C, followed by the dropwise addition of a solution of 2-acetylthiophene (6.3g, 50 mmol, 5.42 mL) and methyl or ethyl ester of the respective perfluorinatedcarboxylic acid (50.5 mmol) in 30 mL of THF. The white suspension rapidly turns pink and then reddish-brown. Caution Hydrogen evolved during the addition and notable effervescence was observed. The rate of addition was maintained to control the evolution of hydrogen; usually the addition takes 60-80 min. When gas evolution ceased, the cooling bath was removed and the reaction mixture was stirred for 5 h. After that, the dark brown solution with a small amount of precipitate was re-cooled to 0 C,10 mL of anhydrous EtOH was added slowly to decompose traces of NaH, and the resulting solution was stirred for 30 min. The solvent was removed by evaporation under reduced pressure (100 Torr, bath temperature 40 C), then EtOAc (40 mL) andsubsequently a mixture of conc. HCl (20 mL) and crushed ice (80 mL) were added tothe residue. The resulting turbid liquid was shaken by hand until two clear layers formed. The organic phase was separated and the aqueous phase was then extracted with EtOAc (3 × 50 mL). The combined organic fractions were washed with brine (50mL), dried over MgSO4 and evaporated to dryness. The resulting brown oil was distilled in vacuo (2-3 Torr). The main fraction is pure enough. Additional portions of pure diketone can be separated from low-boiling fractions by precipitation as a copper salt. Decomposition should be performed with HCl (procedure A).

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 426-65-3.

Reference:
Article; Taydakov, Ilya V.; Kreshchenova, Yuliya M.; Dolotova, Ekaterina P.; Beilstein Journal of Organic Chemistry; vol. 14; (2018); p. 3106 – 3111;,
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Reference of 344-14-9, A common heterocyclic compound, 344-14-9, name is Dimethyl 2-fluoromalonate, molecular formula is C5H7FO4, 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.

Part A: 5-Fluoro-4,6-dihydroxy-2-methylpyrimidine A solution of 200 ml. of 25% wt sodium methoxide in methanol (0.84 mol) was diluted with an additional 200 ml. of methanol. Acetamidine-HCI (40 g , 0.42 mol) was added to the sodium methoxide solution (white precipitate formed), followed by addition of dimethyl fluoromalonate (70 g, 0.46 mol). The contents were stirred at room temperature overnight, then concentrated in vacuo to dryness. The resulting residue was redissolved in hot water (300 ml_). After cooling the aqueous solution to room temperature, concentrated HCI was added slowly until crystal formation (fine white prisms) took place at about pH 5. Concentrated HCI was added dropwise until pH 3, and then the contents were filtered. The isolated crystals were rinsed with 1 M HCI and dried under vacuum to provide 5-fluoro-4,6-dihydroxy-2-methylpyrimidine (65.5 g, >100%). LCMS: (M+H)+: 145.

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; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO. 2) LIMITED; AUBART, Kelly, Marshall; GILLIAN, Jason, Michael; QIN, Donghui; MCKEOWN, Robert, Rahn; WILLIAMS, Glenn, R.; WO2013/82388; (2013); A1;,
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Some common heterocyclic compound, 135908-33-7, name is Methyl 4-aminobicyclo[2.2.2]octane-1-carboxylate, molecular formula is C10H17NO2, 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. HPLC of Formula: C10H17NO2

At RT, 258 mg (1.41 mmol) of methyl 4-aminobicyclo[2.2.2]octane-1-carboxylate, 402 mg (1.06 mmol) of HATU and 182 mg (1.41 mmol) of DIPEA were added to a solution of 210 mg (0.71 mmol) of 6-chloro-3-methyl-2-phenylquinoline-4-carboxylic acid in 5 ml of DMF. The mixture was then stirred at 60 C. for 1 h. After cooling to RT, the mixture was added to 20 ml of a 10% strength citric acid solution. The resulting precipitate was filtered off, washed with water and dried under reduced to pressure. This gave 326 mg (97% of theory, purity 98%) of the title compound. 1H-NMR (400 Mhz, DMSO-d6): delta [ppm]=8.48 (s, 1H), 8.05 (d, 1H), 7.77 (dd, 1H), 7.66 (d, 1H), 7.60-7.47 (m, 5H), 3.59 (s, 3H), 2.32 (s, 3H), 2.09-2.00 (m, 6H), 1.91-1.82 (m, 6H). LC/MS (Method 1, ESIpos): Rt=1.22 min, m/z=463 [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 135908-33-7, its application will become more common.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; BECK, Hartmut; THALER, Tobias; KAST, Raimund; MEININGHAUS, Mark; TERJUNG, Carsten; MUENSTER, Uwe; OLENIK, Britta; (92 pag.)US2018/36300; (2018); A1;,
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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 59833-69-1 as follows. 59833-69-1

General procedure: To a stirred solution of 12e (62 mg, 0.4 mmol) in CH2Cl2 (5 mL) were added a solution of 18 (133 mg, 0.4 mmol) in CH2Cl2 (3 mL) and then pyridine (0.067 mL, 0.8 mmol). After stirring overnight at room temperature, the reaction mixture was diluted with water and extracted with EtOAc (×2). The combined organic layers were washed with 1 M NaOH aq, water, brine, dried over Na2SO4 and concentrated in vacuo. The resulting residue was purified by column chromatography on silica gel to yield methyl ester (120 mg, 63%); TLC Rf = 0.14 (n-hexane/EtOAc, 7:3); 1H NMR (300 MHz, CDCl3) delta 7.60-7.38 (m, 4H), 7.32 (t, J = 7.8 Hz, 1H), 7.06 (d, J = 7.5 Hz, 1H), 6.92-6.77 (m, 4H), 6.74-6.66 (m, 2H), 4.70-4.60 (m, 1H), 4.26 (dd, J = 9.6, 5.4 Hz, 1H), 4.14 (dd, J = 11.4, 6.6 Hz, 1H), 3.71 (s, 3H), 3.65 (s, 2H), 3.39 (dd, J = 11.4, 3.0 Hz, 1H), 3.26 (dd, J = 11.4, 7.8 Hz, 1H), 2.91 (s, 3H), 2.51 (s, 3H).CommentTo a stirred solution of methyl ester (120 mg, 0.25 mmol) described above in MeOH (4 mL) and THF (4 mL) was added 5 M NaOH aq (2 mL). After stirring for 1 h at room temperature, the reaction mixture was diluted with 2 M HCl aq and extracted with EtOAc (×2). The combined organic layers were washed with water, brine, dried over Na2SO4 and concentrated in vacuo to give a crude product, which was washed with EtOAc/n-hexane to yield 4a (85 mg, 73%) as a pale blue powder

According to the analysis of related databases, 59833-69-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Iwahashi, Maki; Takahashi, Eiji; Tanaka, Motoyuki; Matsunaga, Yoko; Okada, Yutaka; Matsumoto, Ryoji; Nambu, Fumio; Nakai, Hisao; Toda, Masaaki; Bioorganic and Medicinal Chemistry; vol. 19; 18; (2011); p. 5361 – 5371;,
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Reference of 33993-24-7,Some common heterocyclic compound, 33993-24-7, name is Cyclopropanecarboxylic anhydride, molecular formula is C8H10O3, 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.

A mixture of 20 g (136 mmol) 1 ,3,5-triazine-2,4-diamine hydrochloride (GAS-No of free base:504-08-5), 500 mL water and 20 g (130 mmol) cyclopropanecarbonyl cyclopropanecarboxylate was stirred for 1 day at RT. 20 g (130 mmol) cyclopropanecarbonylcyclopropanecarboxylate was added into the reaction and stirring was continued for 1 day at room temperature. Another batch of 20 g (130 mmol) cyclopropanecarbonyl cyclopropanecarboxylate was added and stirring was continued for 3 days at room temperature. The above procedure was repeated once and the solutions of two batch reaction were combined. The solids were filtered off and the crude product purified by FlashPrep-HPLC (column: 018 silica gel; mobile phase, ACN/water (0.05% NH4OH) =5% increasing to ACN/water (0.05% NH4OH)=20% within 12 mm; Detector, UV 254 nm) to give10.5 g (22%) of the title compound.LC-MS: m/z = 180 [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 Cyclopropanecarboxylic anhydride, its application will become more common.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; BAYER AKTIENGESELLSCHAFT; KLAR, Ulrich; BOHLMANN, Rolf; SCHAeCKE, Heike; SUeLZLE, Detlev; MENZ, Stephan; PANKNIN, Olaf; (249 pag.)WO2018/134148; (2018); A1;,
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Electric Literature of 27492-84-8, These common heterocyclic compound, 27492-84-8, name is Methyl 4-amino-2-methoxybenzoate, 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 solution of the 4 (0.48 g, 2 mmol), 3-fluoroaniline (0.24g,2.2 mmol) in isopropanol (30 ml) were stirred at 90 C for 4 h.Isopropanol was removed under reduced pressure and the residuewas purified through a column chromatography on silica withchloroform/methanol (V:V 50:1) as a white solid (0.58 g, 91.8percentyield).

The synthetic route of 27492-84-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ding, Huai-Wei; Deng, Cheng-Long; Li, Dan-Dan; Liu, Dan-Dan; Chai, Shao-Meng; Wang, Wei; Zhang, Yan; Chen, Kai; Li, Xin; Wang, Jian; Song, Shao-Jiang; Song, Hong-Rui; European Journal of Medicinal Chemistry; vol. 146; (2018); p. 460 – 470;,
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Reference of 344-14-9, A common heterocyclic compound, 344-14-9, name is Dimethyl 2-fluoromalonate, molecular formula is C5H7FO4, 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: In a 50 mL two-necked flask containing dichloromethane (10 mL) were added the amine (17 mmol) followed by the aldehyde (15 mmol) and the resulting reaction mixture was allowed to stir at rt for 2 h, before the fluorinated dicarbonyl system (10 mmol) was added. The reaction mixture was stirred at rt for 16 h, evaporated and the residue dissolved in dichloromethane (20 mL), washed with distilled water (2×20 mL), dried over magnesium sulfate and evaporated, to give the desired product. Further purification by distillation or column chromatography eluting from hexane/ethyl acetate was carried out when appropriate. Analytical and spectroscopic data for each individual compound are listed below. For NMR data only resonances of one diastereoisomer or conformer is given for clarity.

The synthetic route of 344-14-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Lisse, Etienne; Sandford, Graham; Journal of Fluorine Chemistry; vol. 206; (2018); p. 117 – 124;,
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Application of 4897-84-1, A common heterocyclic compound, 4897-84-1, name is Methyl 4-bromobutanoate, molecular formula is C5H9BrO2, 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 the methyl ester (XIV, 1.8 g, 0.15 mmol) in DMF (50 mL), is added 4-bromo-butyric acid methyl ester (1 g, 0.87 mmol) and Cs2CO3 (800 mg, 0.48 mmol). The reaction is stirred at 22° C. for 48 hours. 5 g SiO2 is added to the mixture and all solvents were evaporated in vacuo. The solid is purified by flash chromatography, eluting with MeOH/DCM (0-10percent) to provide 1.5 g (75percent), of a yellow solid. MS m/z 1357 (M +H2O).

The synthetic route of 4897-84-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bushell, Simon; LaMarche, Matthew J.; Leeds, Jennifer; Whitehead, Lewis; US2009/156628; (2009); 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. 63485-50-7, name is cis-Methyl 3-hydroxycyclobutanecarboxylate, A new synthetic method of this compound is introduced below., name: cis-Methyl 3-hydroxycyclobutanecarboxylate

cis-3-hydroxycyclobutylcarboxylic acid methyl ester (2730 g, 21.0 mol, 1.0 eq) prepared in Example 1 was dissolved in tetrahydrofuran (30 L) and cooled to -10 C.p-Nitrobenzoic acid (4178 g, 25.0 mol, 1.2 eq.), diethyl azodicarboxylate (4354 g, 25.0 mol, 1.2 eq.), triphenylphosphine (6557 g, 25.0 mol, 1.2 eq.).It was then stirred at room temperature for 16 h under nitrogen.The reaction was complete by TLC, the tetrahydrofuran was removed, and methyl t-butyl ether (20 L) was added and stirred for 0.5-1 h.Filter and filter cake was washed twice with methyl tert-butyl ether.All filtrates were collected and the filtrate was washed with saturated aqueous sodium bicarbonate.Dispense, dry and concentrate.The crude product was then beaten with a mixed solvent of ethyl acetate/petroleum ether, filtered and concentrated to give a pale yellow powder.Trans-III compound trans-p-nitrobenzoic acid (3-methoxycarbonylcyclobutyl) ester (4468 g, 16.0 mol), yield 76%, purity 95%.

The synthetic route of 63485-50-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shanghai Bide Pharmaceutical Technology Co., Ltd.; Xiong Shichuan; Mi Taoran; Fan Jianjian; Zhang Ruihao; (9 pag.)CN108129288; (2018); A;,
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