Tag: M.W=100-200

Synthetic Route of 1459-93-4,Some common heterocyclic compound, 1459-93-4, name is Dimethyl isophthalate, molecular formula is C10H10O4, 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.

Magnesium (6.53 g, 25.75 mmol) was suspended in anhydrous THF (50 mL). The solution was cooled at -5 C in a ice-salt bath and a solution of (E)-1-(3-bromobut-1-enyl)benzene 3 (5.43g, 25.75 mmol) in THF (30 mL) was added dropwise over 1h at such a rate that the internal reaction temperature did not exceed 0C. Upon completion of the addition, the reaction mixture was stirred for 1h from 0 to -10 C. The solution was cooled to – 80 C in a liquid nitrogen-acetone freezing mixture. A solution of dimethylisophthalate (5 g, 25.75 mmol) in THF (40 mL) was added dropwise during 1h with vigorous stirring. Then the mixture was stirred at room temperature overnight. A 10% aqueous solution of H2SO4 (100mL) was added to the cooled reactionmixture. Two phases separated and the aqueous layer was extracted with ether (2×50 mL). The combined ethereal extracts were successively washed with a saturated aqueousNaHCO3 solution, water and finally dried over anhydrous magnesium sulfate. After removal of solvent, the resulting residue was purified on a silicagel column eluted with hexane/ethyl acetate 20:1 to give the corresponding aryl ketone(77%). []D20 = – 5.2 (c 0.1 AcOEt) with spectral data identical to those of product from procedure 1.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Dimethyl isophthalate, its application will become more common.

Reference:
Article; Mezrai; Drici; Lesur; Kajima Mulengi; Wadouachi; Pilard; Letters in Organic Chemistry; vol. 11; 4; (2014); p. 259 – 267;,
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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. 42122-44-1, name is Methyl 3-(4-fluorophenyl)propiolate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C10H7FO2

The product thus obtained was dissolved in DMF (2,4 mL) and added slowly dropwise over 20 min to a cooled mixture (00C, ice bath) containing potassium carbonate (0.070 g, 0.50 mmol), methyl 3-(4-fluorophenyl)propiolate (0.030 g, 0.19 mmol) and DMF (2.0 mL). The mixture was kept in the cooling bath with stirring and allowed to proceed for 15 h at ambient temperature. The mixture was filtered and concentrated. Purification on silica gel (0-100% ethyl acetate/hexanes, 60 min gradient) afforded methyl 2-(4-fluorophenyl)-6-(N-(2- hydroxyethyl)methylsulfonamido)-5-(3-(2-phenylpropan-2-ylcarbamoyl)phenyl) pyrazolo[lj5-a]pyridme-3-carboxylate as a yellow residue. IH NMR (500 MHz, CHLOROFORM-D) delta ppm 8.72 (s, 1 H), 8.24 (s, 1 H), 8.16 (s, 1 H), 7.97 – 8.00 (m, 1 H), 7.89 (t, J-7.93 Hz, 1 H), 7,77 – 7.84 (m, 2 H), 7.50 – 7.59 (m, 2 H)5 7.40 – 7.49 (m, 3 H), 7.23 – 7.33 (m, 3 H)9 7.12 – 7.19 (m, 3 H), 3.83 (s, 3 H), 3.62 – 3.71 (m, 1 H), 3.39 – 3.46 (m, 1 H), 3.30 – 3.39 (m, 1 H), 3.18 – 3.23 (m, 3 H), 2.63 – 2.72 (m, 1 H), 1.78 (t, J=I 2.21 Hz, 6 H). LCMS: retention time: 2.403 min. LC data was recorded on a Shimadzu LC-IOAS liquid chromatograph equipped with a Waters- Sunfre, 5u, C 18, 4.6 x 50 mm column using a SPD-10AV UV- Vis detector at a detector wave length of 220 nM. The elution conditions employed a flow rate of 4 mL/min, a gradient of 100% solvent A / 0% solvent B to 0% solvent A / 100% solvent B, a gradient time of 3 min, a hold time of 1 min, and an analysis time of 4 min where solvent A was 10% CH3CN / 90% H2O / 10 mM TFA and solvent B was 10% H2O / 90% CH3CN / 10 mM TFA. MS data was determined using a Micromass Platform for LC in electrospray mode, m/z 645 (MH+).

The synthetic route of 42122-44-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; PRACITTO, Richard; KADOW, John F.; BENDER, John A.; BENO, Brett R.; GRANT-YOUNG, Katharine A.; HAN, Ying; HEWAWASAM, Piyasena; NICKEL, Andrew; PARCELLA, Kyle E.; YEUNG, Kap-Sun; CHUPAK, Louis S.; WO2010/30538; (2010); A2;,
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Synthetic Route of 89-91-8, 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 89-91-8 as follows.

The synthesis of {5-Bromo-l-[3-(methylsulfonyl)propyl]-lH-benzimidazol-2-yl}- methanol (fragment A2) was done as shown in scheme 6. refluxed overnightfragment A2Scheme 6 Compound 1 (7.6 g, 35 mmol), 3 -(methyl sulfonyl)propan-l -amine hydrochloride (6 g, 35 mmol) and diisopropylethylamine (DIEA) (13.5 g, 105 mmol) were dissolved in ethanol (70 mL) and refluxed for 14 h. The mixture was cooled to 20C. The precipitate was filtered and washed with ethanol. 11 g (94%) of compound 2 was obtained as an orange powder. Compound 2 (10 g, 29.7 mmol) in methanol (200 mL), EtOAc (200 mL) and THF (200 mL) was hydrogenated with Raney Ni (10 g) as a catalyst at 20C (1 atm) for 3h. After uptake of H2 (3 eq), the catalyst was filtered off and the filtrate was evaporated. 10 g (90%) of compound 3 was obtained as a black solid.Compound 3 (10 g, 29.7 mmol) and methyl dimethoxyacetate (9.2 g, 68.31 mmol) in 24 wt% KOEt in ethanol (13.5 g, 38.5 mmol) were stirred and refluxed overnight. The mixture was evaporated under vacuum. Water (200 mL) was added. Acetic acid was added to neutralize the mixture. The mixture was extracted with ethyl acetate (2×100 mL). The combined organic layers were washed with saturated NaHC03, brine and dried over Na2S04. The solvent was removed under vacuum to yield 12.3 g (90%) of compound 4 as dark oil. Compound 4 (12.3 g, 29.3 mmol) in THF (100 mL) was stirred for 0.5 h at 20C to dissolve. Cone. HCI (21 mL) and H20 (42 mL) were added.The mixture was refluxed for 6 h and then cooled to -10C. CH3OH (50 mL) were added, followed by careful addition of NaBH4 (24 g, 629 mmol). The mixture was stirred for 0.5 h at 10C and concentrated under vacuum. Water (200 mL) was added.The mixture was extracted with ethyl acetate (2×100 mL). The combined organic layers were washed with brine and dried over Na2S04. The solvent was removed under vacuum. The resulting solid was washed with ethyl acetate (2×5 mL) and dried under vacuum. 6.8 g (60%) of fragment A2 was obtained as an off-white solid, m/z = 347 & 349 (M+H)+Br pattern. 1H NMR (400 MHz, DMS0 ) delta ppm 2.20 (dq, J=7.8, 7.5 Hz, 2 H), 2.98 (s, 3 H), 3.16 – 3.24 (m, 2 H), 4.42 (t, J=7.4 Hz, 2 H), 4.73 (d, J=6.0 Hz, 2 H), 5.73 (t, J=5.8 Hz, 1 H), 7.42 (dd, J=8.7, 1.9 Hz, 1 H), 7.63 (d, J=8.5 Hz, 1 H), 7.79 – 7.83 (m, 1 H)

According to the analysis of related databases, 89-91-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JANSSEN R&D IRELAND; COOYMANS, Ludwig Paul; DEMIN, Samuel Dominique; HU, Lili; JONCKERS, Tim Hugo Maria; RABOISSON, Pierre Jean-Marie Bernard; TAHRI, Abdellah; VENDEVILLE, Sandrine Marie Helene; WO2012/80446; (2012); A1;,
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Adding a certain compound to certain chemical reactions, such as: 56741-34-5, name is Methyl 5-amino-2-fluorobenzoate, 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 56741-34-5, Recommanded Product: Methyl 5-amino-2-fluorobenzoate

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

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

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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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 13195-64-7 as follows. HPLC of Formula: C9H16O4

General procedure: At room temperature, to a solution of nitroalkenes 2 (0.2 mmol) and chiral catalyst Q4 or QD4 in THF was added dimethyl malonate 3 (68 muL, 0.3 mmol). The resulting mixture was purified by flash chromatography when 2 was consumed through a TLC analysis to afford the product 4 or 5.

According to the analysis of related databases, 13195-64-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Li, Fei; Li, Ying-Zi; Jia, Zhen-Shan; Xu, Ming-Hua; Tian, Ping; Lin, Guo-Qiang; Tetrahedron; vol. 67; 52; (2011); p. 10186 – 10194;,
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Electric Literature of 89-91-8, 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. 89-91-8 name is Methyl 2,2-dimethoxyacetate, 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.

Lithium hexamethyldisilane (55 mL of a 1 .OM solution in tetrahydrofuran, 55mmoles) was added to a solution of 3-acetylpyridine (5.5 mL, 50 mmoles), methyl dimethoxy acetate (6.7 mL, 55 mmoles) and anhydrous tetrahydrofuran (100 mL) with cooling at -45 C. The resulting reaction mixture was allowed to warm to 25 C over 1 hour, and stirred at this temperature for 3 hours. The reaction mixture was then concentrated under reduced pressure, and the residue was suspended in methanol (50 mL) andconcentrated under reduced pressure. The resulting residue was suspended in methanol (150 mL) and treated with hydrazine monohydrate (2.62 mL, 55 mmoles) and glacial acetic acid (6.29 mL, 110 mmoles), and the reaction mixture was heated at reflux for 14 hours. The resulting reaction mixture was cooled to 25 C and concentrated under reduced pressure. The residue was partitioned between ethyl acetate (200 mL) and iN aqueous sodiumhydroxide solution (100 mL). The layers were separated, and the organic layer was washed successively with iN aqueous sodium hydroxide solution (50 mL) and brine (50 mL), dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to yield 8.83 g of the title compound as a beige solid. 1H NMR (CDC13): oe 10.5 (br s, 1H) 9.03 (d, 1H), 8.57 (dd, 1H), 8.09 (dt, 1H), 7.34(dd, 1H), 6.65 (s, 1H), 5.63 (s, 1H), 3.39 (s, 6H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 2,2-dimethoxyacetate, and friends who are interested can also refer to it.

Reference:
Patent; E. I. DU PONT DE NEMOURS AND COMPANY; CLARK, David, Alan; FRAGA, Breena, Gloriana; ZHANG, Wenming; WO2015/38503; (2015); A1;,
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Adding a certain compound to certain chemical reactions, such as: 25597-16-4, name is Ethyl 4,4,4-trifluorocrotonate, 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 25597-16-4, SDS of cas: 25597-16-4

[0319] A mixture of 4-benzyl-2-hydroxy-3-methylbenzaldehyde prepared as in Step 4 (1.07 g, 4.73 mmole), K2C03 (0.654 g, 4.73 mmole) and ethyl 444-trifluocrotonate (484 uL, 5.67 mmole) in anhydrous DMF (5.0 mL) was heated to 85 C under a dry N2 atmosphere for 2.75 h. The mixture was then cooled, poured into IN HC1 (100 ml) and extracted with EtOAc (2 X 100 mL). The combined extracts were washed with brine (100 mL), dried over MGS04, filtered and concentrated in vacuo to give 1.86 g of a yellow oil. The crude product was purified by silica chromatography (95: 5 hexanes: EtOAc) to give 1.04 g (59% yield) of the product as a light yellow oil: EIHRMS NILZ 376. 1310 (M+, C21H19F3O3, Calc’d 376.1286).

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

Reference:
Patent; PHARMACIA CORPORATION; WO2004/87686; (2004); A2;; ; Patent; PHARMACIA CORPORATION; WO2004/87687; (2004); A1;,
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These common heterocyclic compound, 2318-25-4, name is Ethyl 3-ethoxy-3-iminopropionate hydrochloride, 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. HPLC of Formula: C7H14ClNO3

A solution of 1, 2-phenylenediamine (1.0 equivalent) and ethyl 3- ETHOXY-3-IMINOPROPANOATE hydrochloride (1.3 equivalents) in ethanol was stirred at 90 C overnight. The reaction was cooled to room temperature and the solvent was removed in vacuo. Water and CH2CI2 were added to the residue. The organic layer was separated, dried over NA2SO4 and the solvent removed. The solid recovered was used without purification. LC/MS M/Z 205.2 (MH+), RIF 1. 44 minutes.

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

Reference:
Patent; CHIRON CORPORATION; WO2004/18419; (2004); A2;,
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Reference of 40061-54-9, 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 40061-54-9 as follows.

Step 4. DBU (4.1 g, 26.9 mmol, 1.2 eq) was added to a mixture of 4-(methylamino)-2-(methylthio)-pyrimidine-5-carbaldehyde (4.1 g, 22.4 mmol, 1.0 eq) and ethyl 2-(2-chlorophenyl)acetate (5.4 g, 26.9 mmol, 1.2 eq) at RT. The resulting mixture was then stirred at room temperature for 1 h, followed by addition of water and extraction with EtOAc. The combined organic layers were dried and concentrated to afford 6-(2-chlorophenyl)-8-methyl-2-(methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one (5.0 g, 70percent in yield).

According to the analysis of related databases, 40061-54-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Taunton, JR., John William; Brameld, Kenneth Albert; Goldstein, David Michael; Mcfarland, Jesse; Krishnan, Shyam; Choy, Jonathan; US2014/323464; (2014); 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. 18469-52-8, name is Methyl 4-(aminomethyl)benzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. SDS of cas: 18469-52-8

A solution of methyl 4-(aminomethyl)benzoate (2.000 g, 9.918 mmol), morpholine- 4-carbonyl chloride ( 1.635 g, 10.910 mmol) and N,N-diisopropylethylamine (5.183 mL, 29.755 mmol) in dichloromethane (20 mL) was stirred at the room temperature for 12 hr. The reaction mixture was concentrated under the reduced pressure to remove the solvent, and water was added to the concentrate, followed by extraction with dichloromethane. The organic layer was washed with aqueous saturated sodium chloride solution, dried (anhydrous MgS04), filtered, and concentrated in vacuo. The concentrate was purified and concentrated by column chromatography (SiO:, 12 g cartridge; ethyl acetate / hexane = 0 % to 50 %) to give the title compound methyl 4-((morpholine-4-carboxamido)methyl)benzoate as White solid (2.200 g. 79.7 %).

The synthetic route of 18469-52-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CHONG KUN DANG PHARMACEUTICAL CORP.; LEE, Jaekwang; KIM, Yuntae; LEE, Chang Sik; SONG, Hyeseung; GWAK, Dal-Yong; LEE, Jaeyoung; OH, Jung Taek; LEE, Chang Gon; KIM, II Hyang; (1041 pag.)WO2017/23133; (2017); A2;,
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