Tag: M.W=200-300

Reference of 457097-93-7, 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. 457097-93-7, name is Methyl 4-amino-3-(trifluoromethoxy)benzoate, This compound has unique chemical properties. The synthetic route is as follows.

[Step 1] 4-[(Ethylsulfonyl)amino]-3-(trifluoromethoxy)benzoic acid Using methyl 4-amino-3-(trifluoromethoxy)benzoate (300 mg) and ethanesulfonyl chloride (0.724 ml), synthesis was carried out in the same manner as in Step 1 of Example 8 to obtain the title compound (408 mg) as a solid. 1H-NMR (DMSO-D6) delta: 1.25 (3H, t, J=7.3 Hz), 3.27 (2H, q, J=7.3 Hz), 7.69 (1H, d, J=9.2 Hz), 7.80-7.84 (1H, m), 7.91 (1H, dd, J=8.5, 1.8 Hz), 10.27 (1H, s), 13.31 (1H, br s). MS (ESI/APCI) m/z: 312 [M-H]-

The chemical industry reduces the impact on the environment during synthesis Methyl 4-amino-3-(trifluoromethoxy)benzoate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Daiichi Sankyo Company, Limited; Ota, Masahiro; Inoue, Hidekazu; Kawai, Junya; Ohki, Hitoshi; Toki, Tadashi; (25 pag.)US2019/284198; (2019); A1;,
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Synthetic Route of 52727-57-8, A common heterocyclic compound, 52727-57-8, name is Methyl 2-amino-5-bromobenzoate, molecular formula is C8H8BrNO2, 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.

Example 54; 2-Amino-5-(2-11-[(4-aminomethyl-cyclohexanecarbonyl)-aminol-2-phenyl-ethyll- pyridin-4-yl)-benzoic acid methyl ester, tris-trifluroacetic acid salt; [00404] 54A. 2-Amino-5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-benzoic acid methyl ester: To a flame-dried, round-bottom flask equipped with a condenser was added 2-Amino-5-bromo-benzoic acid methyl ester (0.7 g, 3.0 mmol), Pd (dppf)Cl2No.CH2Cl2 complex (0.106 g, 0.130 mmol), KOAc (1.28 g, 13.0 mmol), and bis(neopentyl glycolato) diboron (1.08 g, 4.78 mmol). Next degassed DMSO (29 mL) was added and the reaction was stirred at 80 C. After 5 h, the reaction was cooled to rt, diluted with EtOAc (100 mL), washed with water, brine, dried over Na2S04, filtered and concentrated. Column chromatography on silica gel (gradient elution 0- 20% EtOAc/Hexane) gave 54A (0.858 g, 75%) as a white solid. ?H NMR (400 MHz, CDC13) 8: 1.01 (s, 6 H), 3.74 (s, 4 H), 3.86 (s, 3 H), 5.91 (bs, H), 6.63 (d, J = 8.3 Hz, 1 H), 7.66-7.68 (m, 1 H), 8.33 (s, 1 H). MS 196.1 (M – C5H8 + H)+.

The synthetic route of 52727-57-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2005/123680; (2005); A1;,
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Adding a certain compound to certain chemical reactions, such as: 14273-90-6, name is Methyl 6-bromohexanoate, 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 14273-90-6, Quality Control of Methyl 6-bromohexanoate

(1) 1,2,3,4-Tetrahydroquinoline (0.50 mL, 3.98 mmol) and methyl 6-bromohexanoate (0.76 mL, 4.78 mmol) were added to MeCN (30 mL) containing KI (1.59 g, 9.58 mmol) and K2CO3 (1.10 g, 7.96 mmol) dissolved therein, and the suspension was stirred at 100 C. for 21 hours in an argon atmosphere. The reaction solution was cooled to room temperature and then diluted with water, followed by extraction with ethyl acetate. The organic phase was washed with saturated saline, dried over Na2SO4, and dried under reduced pressure. The residue was purified by flash column chromatography (hexane/EtOAc=100/0 to 80/20) to obtain N-methoxycarbonylpentyl-1,2,3,4-tetrahydroquinoline (1.10 g, 100%). Colorless oil; 1H NMR (500 MHz, CDCL3) delta: 7.02 (t, J=7.5 Hz, 1H), 6.91 (d, J=7.5 Hz, 1H), 6.51-6.54 (m, 2H), 3.66 (s, 3H), 3.20-3.26 (m, 4H), 2.73 (t, J=6.3 Hz, 2H), 2.31 (t, J=7.5 Hz, 2H), 1.90-1.94 (m, 2H), 1.63-1.69 (m, 2H), 1.56-1.62 (m, 2H), 1.32-1.38 (m, 2H); LRMS (ESI): m/z calcd [M+H]+ 262.2, found 262.0.

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:
Patent; JAPAN SCIENCE AND TECHNOLOGY AGENCY; KANAI, Motomu; SOMA, Yohei; TANIGUCHI, Atsuhiko; SHIMIZU, Yusuke; (45 pag.)US2017/197956; (2017); A1;,
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Adding a certain compound to certain chemical reactions, such as: 1150566-27-0, name is Ethyl 6-chloroimidazo[1,2-b]pyridazine-3-carboxylate, 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 1150566-27-0, category: esters-buliding-blocks

To a suspension of ethyl 6-chloroimidazo[1,2-b]pyridazine-3-carboxylate (I-7) (128 mg, 0.565 mmol) in DMSO (2.5 mL) was added (3S)-3-(tert-butyldimethylsilyloxy)-2-(3-fluorophenyl)pyrrolidine (I-53) (167 mg, 0.565 mmol) and potassium floride (328 mg, 5.65 mmol). The mixture was heated at 120 C. overnight. The mixture was poured into water and extracted with EtOAc twice. The combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated. The crude product was purified by column chromatography on silica gel with EtOAc/hexanes gradient as eluant to yield ethyl 6-((3S)-2-(3-fluorophenyl)-3-hydroxypyrrolidin-1-yl)imidazo[1,2-b]pyridazine-3-carboxylate (I-54). MS m/z 371.1 (M+1)+.

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 6-chloroimidazo[1,2-b]pyridazine-3-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; IRM LLC; US2012/65184; (2012); A1;,
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Synthetic Route of 756525-95-8,Some common heterocyclic compound, 756525-95-8, name is tert-Butyl 9-Amino-4,7-dioxanonanoate, molecular formula is C11H23NO4, 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 stirred solution of carboxylic acid 10 (30 mg, 0.125 mmol), HATU (53 mg, 1.38 mmol) and DIPEA (70 L, 0.375 mmol) in DMF (5 mL) at 25 C was added the corresponding primary amine (33 mg, 0.138 mmol). The reaction mixture was stirred for 16 h, diluted with 0.1 N aqueous NaOH (15 mL) and extracted with CH2C12 (3 x 20 mL). The combined organic phases were dried over anhydrous Na2S04 and concentrated under reduced pressure. The residue was purified by flash column chromatography (0-5 % MeOH in DCM) to give compound M (18 mg, 0.040 mmol, 32% yield). MS (ESI) m/z 456 (M+H)+

The synthetic route of 756525-95-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DANA-FARBER CANCER INSTITUTE, INC.; THE GENERAL HOSPITAL CORPORATION D/B/A MASSACHUSETTS GENERAL HOSPITAL; GRAY, Nathanael S.; HAGGARTY, Stephen J.; CAI, Quan; TELO BAPTISTA LIMA DA SILVA, Maria Catarina; ZHANG, Tinghu; FERGUSON, Fleur M.; (220 pag.)WO2019/14429; (2019); 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 620-72-4 as follows. Quality Control of Phenyl 2-bromoacetate

To a solution of phenylbromoacetate (18.58 g, 86 mmol) in CH3CN under nitrogen was added a solution of (R)-phenylglycinol (10.17 g, 74 mmol) and di-isopropylethylamine (34 ml_, 195 mmol) in CH3CN. The volatiles were removed under reduced pressure keeping the bath temperature below 25 0C to obtain an oil that was treated with EtOAc (120 mL) and stirred for 15 min. The resulting white precipitate was removed by filtration. The filtrate was concentrated under reduced pressure and the desired product was isolated using column chromatography (SiO2) with a step gradient of 10 percent to 50 percent [v/v] EtOAc in cyclohexane to give after evaporation (f?)-5-phenylmorpholin-2- one EBE 06134 (3.17 g, 24 percent yield) as a white solid.MW: 177.2; Yield: 24 percent; White Solid; Mp (0C): 50.3Rf\ 0.30 (EtOAc:cyclohexane = 50:50). 1H-NMR (CDCI3, delta): 1.99 (s, 1 H, NH), 3.89 (q, 2H, J = 17.8 Hz, N-CH2), 4.18(dd, 1 H, J = 3.7 Hz, J = 10.3 Hz, 0-CH), 4.29 (t, 1 H, J = 10.5 Hz, N-CH), 4.40(dd, 1 H, J = 3.7 Hz, J = 10.5 Hz, 0-CH), 7.30-7.45 (m, 5H, ArH).13C-NMR (CDCI3, delta): 46.8, 54.8, 72.8, 125.3 (2xC), 127.0, 127.3 (2xC), 135.9,166.0. [G]22D = + 30.3 ¡ã (c = 1.00, MeOH).

According to the analysis of related databases, 620-72-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ALLERGAN, INC.; WO2008/11478; (2008); A2;,
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Some common heterocyclic compound, 1236357-65-5, name is Methyl 1-(4-bromophenyl)cyclobutanecarboxylate, molecular formula is C12H13BrO2, 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. name: Methyl 1-(4-bromophenyl)cyclobutanecarboxylate

Step 1. Methyl l-(4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2- yl)phenyl)cyclobutane-l -carboxylate: Into a 40 ml vial equipped with a magnetic stir bar and under N2 were added 4,4,5,5-tetramethyl-2-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-l,3,2- dioxaborolane (2.26 g, 8.92 mmol), methyl l-(4-bromophenyl)cyclobutanecarboxylate (2 g, 7.43 mmol), Pd(dppf)C12, complex with DCM (307.18 mg, 371.56 muiotatauiotaomicron) and potassium acetate (2.19 g, 22.29 mmol). The vial was evacuated under vacuum and refilled with N2. DMF (15 mL) was added, and the mixture was degassed for 10 minutes with N2 and then heated to 100 C O/N. The black reaction mixture was cooled to RT, and purified by column chromatography through silica gel eluting with 100:0 to 0: 100 Hexanes:EtOAc as a gradient over 25 minutes. The desired fractions were combined, concentrated and further dried under high vacuum O/N to provide a yellow solid (1.6 g) LCMS (ESI+) m/z = 317 (M+l).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1236357-65-5, its application will become more common.

Reference:
Patent; TEMPEST THERAPEUTICS, INC.; POWELL, David Andrew; ROPPE, Jeffrey Roger; SEIDERS, Thomas Jon; DING, Jinyue; SHENG, Tao; JACINTHO, Jason Duarte; (65 pag.)WO2019/79614; (2019); A1;,
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These common heterocyclic compound, 110661-91-1, name is tert-Butyl 4-bromobutanoate, 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. Product Details of 110661-91-1

General procedure: To 100 mLrbf was added a mixture of compound 20 (1.66 g, 10 mmol), cesiumcarbonate (3.26 g, 10 mmol), TBAI (3.70 g, 10 mmol) and anhydrousDMF (20 mL). Compound 19 (2.23 g, 10 mmol) was added dropwise tothe mixture. The reaction mixture was then stirred at room temperaturefor 3 h. Ethyl acetate was added into the reaction mixture. The combinedmixture was washed with two portions of water. After evaporationof the solvent under reduced pressure MeOH (20 mL) was addedfollowed by silica gel (1 g). The resulting plug was loaded on to a silicagel column and eluted with 1:10 (ethyl acetate: hexane). Fractions withand Rf = 0.64 (hexane:ethyl acetate 1:1) were pooled and evaporatedto afford tert-butyl esters (1.47 g, yield; 47%). Trifluoroacetic acid wasthen added into the tert-butyl esters and mixture was stirred at roomtemperature for 30 min. Excess of trifluoroacetic acid was evaporatedand MeOH (20 mL) was added followed by silica gel (1 g). The resultingplug was loaded on to a silica gel column and eluted with 1:10 (ethylacetate: hexane). Fractions with and Rf = 0.45 (TLC) (Hexane: ethylacetate,1:1) were pooled and evaporated to afford 22 (1 g, yield 83%)as white solid.

The synthetic route of tert-Butyl 4-bromobutanoate has been constantly updated, and we look forward to future research findings.

Reference:
Article; Dekhne, Aamod S.; Gangjee, Aleem; Golani, Lalit K.; Hou, Zhanjun; Islam, Farhana; Matherly, Larry H.; O’Connor, Carrie; Bioorganic and medicinal chemistry; vol. 28; 12; (2020);,
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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. 17100-63-9, name is Methyl 4-bromo-3-methoxybenzoate, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 17100-63-9

To a solution of methyl 4-bromo-3-methoxybenzoate (1.32 g, 5.39 mmol) in dioxane (30 mL) and water (5 mL) were added tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-carboxylate (1.90 1 g, 6.46 mmol), potassium phosphate (2.86 g, 13.47 mmol) and PdC12(dppf) (0.197 g, 0.269 mmol) at rt. The reaction was stirred under argon at 100 C for 3 hrs. The reaction mixture was diluted with EtOAc, washed with H20. The organic phase was dried over sodium sulfate, filtered and concentrated. The residue was dissolved in DCM (10 mL) and TFA (5 mL) wasadded. The reaction was stirred at rt for 1.5 hrs. Solvent was removed. The residue was taken into EtOAc, which was washed with NaHCO3 (3x) and brine, dried over Na2504, filtered and concentrated. The crude product was purified by normal phase chromatography. Desired product was isolated as white solid (0.86 g, 69% yield).LCMS(ESI) m/z: 233.0 (M+H) ?H NMR (400MHz, CDC13) oe 8.13 (s, 2H), 7.73 – 7.66(m, 1H), 7.66 – 7.56 (m, 2H), 3.98 (s, 3H), 3.94 (s, 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 17100-63-9.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; LADZIATA, Vladimir; GLUNZ, Peter W.; HU, Zilun; WANG, Yufeng; (0 pag.)WO2016/10950; (2016); A1;,
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2557-13-3, name is Methyl 3-(trifluoromethyl)benzoate, 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. Product Details of 2557-13-3

In a first step of Method C as illustrated here, N-(2-amino-1-propyl)-3-(trifluoromethyl)benzamide is prepared as an intermediate. A mixture of 4.1 g (20 mmol) methyl 3-(trifluoromethyl)benzoate and 5.9 g (80 mmol) 1,2-diaminopropane is stirred at room temperature for 24 h, and is then placed under high vacuum (0.1 mm Hg) and stirred at room temperature for a further 24 h to remove by volatilization excess 1,2-diaminopropane. The resulting gummy solid is triturated with 50 ml of a 1:1 mixture of ether and hexane, followed by filtration to give a white solid. Recrystallization of the crude product from ether-hexane gives 3.6 g (65% yield) N-(2-amino-1-propyl)-3-(trifluoromethyl)benzamide as a white crystalline material: 1H NMR (DMSO-d6) delta 0.98 (3H, d, J=7 Hz), 2.95 (1H, m), 3.18 (2H, m), 3.43 (1H, br s), 7.70 (2H, t, J=7 Hz), 7.88 (1H, d, J=7 Hz), 8.18 (2H, m), 8.68 (1H, br s).

The synthetic route of 2557-13-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hegde, Shridhar G.; Krupa, Daniel M.; Bohn, Joseph A.; Coffen, David L.; Gustafson, Gary R.; Kaplan, Alan P.; Ma, Yuting; US2002/52295; (2002); A1;,
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