Tag: M.W=200-300

Related Products 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 4-(4-(3-(4-chloro-3-(trifluoromethyl)phenyl)ureido- )phenoxy)picolinic acid (08) (200 mg, 0.44 mmol, 1.0 equiv) in DMF (5.0 mL, 25.0 vol. equiv.) were added tert-butyl 3-(2-(2-aminoethoxy)ethoxy)propanoate (10) (124 mg, 0.53 mmol, 1.2 equiv), HATU (505 mg, 1.33 mmol, 3.0 equiv) and DIPEA (68.5 mg, 0.53 mmol, 1.20 equiv). The reaction mixture was stirred for 12h at RT. Completion of reaction was monitored by TLC. The Reaction mixture was quenched with DMW (100 mL) and extracted with EtOAc (100 mL x 3). The combined organic extract was washed with brine (100 mL), dried over Na2S04 and concentrated under vacuum to afford the desired compound (11) (290 mg, 98.20%) as a brown gum. MR (300 MHz, OMSO-d6) delta 9.22 (s, 1H), 9.00 (s, 1H), 8.69 (s, 1H), 8.52-8.51 (d, 1H), 8.13-8.12 (d, 1H), 7.65-7.64 (d, 2H), 7.63 (s, 1H), 7.61-7.60 (d, 1H), 7.58 (s, 1H), 7.39-7.38 (d, 1H), 7.19-7.16 (m, 3H), 3.59-3.41 (m, 16H), 2.89 (s, 2H), 2.41-2.39 (d, 2H) 1.40-1.37 (t, 9H). MS (ES+): 755.0 (M+l); MS (ES-): 753.2 (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 tert-Butyl 9-Amino-4,7-dioxanonanoate, its application will become more common.

Reference:
Patent; QUARTZ THERAPEUTICS, INC.; ZAMBONI, Robert; HENNING, Ryan; JI, Alan; SMITH, Tyler; HELLER, Bradley; REDDY, Thumkunta Jagadeeswar; ROCHELEAU, Sylvain; BEAULIEU, Marc Andre; (266 pag.)WO2018/200981; (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 139102-34-4 as follows. Quality Control of Methyl 4-bromo-2-methoxybenzoate

A solution of 4-bromo-2-methoxybenzoic acid methyl ester (0.1 mol) and tetrahydro- 2H”-pyran-4-amine (0.3 mol) in 1 -methyl-2-pyrrolidinone (800 ml) was stirred at 400C. Cs2CO3 (0.2 mol) was added. The reaction mixture was stirred for 5 minutes. Pd2(dba)3 (0.002 mol) and BINAP (0.003 mol) were added. The reaction solution was degassed by applying alternating nitrogen atmosphere and vacuum. The reaction mixture was stirred overnight at 110C. The 1 -methyl-2-pyrrolidinone solvent was evaporated. The residue was purified by high-performance liquid chromatography. The product fractions were collected and the solvent was evaporated, yielding 13 g of intermediate (29).

According to the analysis of related databases, 139102-34-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; WO2009/62990; (2009); A2;,
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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. 49851-36-7, name is Methyl 2-(2-aminophenyl)acetate hydrochloride, A new synthetic method of this compound is introduced below., Quality Control of Methyl 2-(2-aminophenyl)acetate hydrochloride

To a solution of methyl 2-(2-aminophenyl)acetate hydrochloride (CAS 49851-36-7) (0.50 g, 2.5 mmol) in DMF (24.8 ml) at 0 C was added NBS (0.441 g, 2.48 mmol) and this was stirred at 0 C. After 10 minutes the reaction was quenched with saturated aqueous sodium bicarbonate, extracted with EtOAc, washed with water, dried over MgS04, filtered and concentrated. This was purified by flash chromatography (0-15% EtOAc:DCM) to provide the title compound. MS (ESI+) m/z 244.1 , 246.1 (M+H).

The synthetic route of 49851-36-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; BELANGER, David B.; FLOHR, Stefanie; GELIN, Christine Fang; JENDZA, Keith; JI, Nan; LIU, Donglei; LORTHIOIS, Edwige Liliane Jeanne; KARKI, Rajeshri Ganesh; MAINOLFI, Nello; POWERS, James J.; RANDL, Stefan Andreas; ROGEL, Olivier; VULPETTI, Anna; YOON, Taeyoung; WO2015/9977; (2015); 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. 26218-04-2, name is 2-Ethylhexyl 4-aminobenzoate, A new synthetic method of this compound is introduced below., SDS of cas: 26218-04-2

Example 2Synthesis of 2, 5, 8-tris- (4- (2- ethylhexyloxycarbonyl) phenylamino) -1,3,4,6,7,9, 9b- heptaazaphenalene .A mixture of 2, 5, 8-trichloro-l, 3, 4, 6, 7, 9, 9b- heptaazaphenalene (50 mg, 0.18 mmol) and 2-ethylhexyl 4- aminobenzoate (270 mg, 1.08 mmol) in toluene (2 mL) is refluxed for 1 hour. The solvent is evaporated in vacuo and the crude product is purified by silica gel column chromatography, eluting with hexane / ethyl acetate 2 / 1. 2,5, 8-tris- (4- (2-ethylhexyloxycarbonyl) phenylamino) – 1, 3, 4, 6, 7, 9, 9b-heptaazaphenalene is obtained (160 mg, 0.17 mmol, 97%) . M. P. 183-186 C.1H NMR (300 MHz, DMSO-d6): ? 0,93 (m, 18H), 1,30 (m, 24H), 1,62 (m, 3H), 4,18 (d, J = 5.4 Hz, 6H), 7,95 (m, 12H), 10,85 (m, 3H) .MS-EI (m/z) : 916 (M+l) . UV: ?max = 326 nm; ? = 95000 M”1 cm”1 (CHCl3) .

The synthetic route of 26218-04-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ISDIN, S.A.; WO2007/6807; (2007); A1;,
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Electric Literature of 25542-62-5, The chemical industry reduces the impact on the environment during synthesis 25542-62-5, name is Ethyl 6-bromohexanoate, I believe this compound will play a more active role in future production and life.

In a 50-mL round bottom flask, a stirred solution of substituted 5-bromo-2-hydroxybenzaldehyde (5.0 g, 24.8 mmol) in DMF (30 mL), was treated with potassium carbonate (10.26g, 74.4 mmol) and ethyl 6- bromohexanoate (6.6g, 29.8 mmol) at rt under nitrogen atmosphere. The reaction mixture was heated at 90C for 4 h. Upon completion of the reaction (TLC) the reaction mixture was cooled to rt, diluted with cold water and extracted ethyl acetate (250 mL x 2). The combined organic extract was washed with brine and dried over anhydrous NaiSO t. The solution was concentrated under reduced pressure to give the title compound (7.97 g, 94%) as yellow oil. LCMS (m/z): 343.2 (M+l)+.

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

Reference:
Patent; SALK INSTITUTE FOR BIOLOGICAL STUDIES; MITOKYNE, INC.; EVANS, Ronald; BAIGA, Thomas, J.; BOCK, Mark, G.; DOWNES, Michael; EMBLER, Emi, Kanakubo; FAN, Weiwei; KEANA, John, F.W.; KLUGE, Arthur, F.; NOEL, Joseph, P.; PATANE, Mike, A.; WO2014/165827; (2014); A1;,
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Application of 185312-82-7, 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. 185312-82-7, name is Methyl 4-bromo-2-chlorobenzoate, This compound has unique chemical properties. The synthetic route is as follows.

At 0C, lithium aluminum hydride (1.09 g, 30 mmol) was dropped into a solution of methyl 4-bromo-2-chlorobenzoate (4.78 g, 19.16 mmol) in tetrahydrofuran (100 mL) slowly. The ice-salt bath used was removed after that dropping. The reaction was complete (detected with LCMS and TLC) after stirred for 1 hour at room temperature. The mixture was cooled to 0C again and the reaction was quenched with water (1.09 mL) and 10% NaOH solution (10.9 mL) respectively. After stirred for 15 min at room temperature, the mixture was filtered and then the filter cake was washed with tetrahydrofuran (50 mLx2) and ethyl acetate EA (50 mLx2). The filtrate was dried with anhydrous sodium sulfate, filtered, and then concentrated to obtain a colorless oil product (3.4 g, 80% yield). The molecular ion peak shown by liquid chromatography-mass spectrometry was: MS (ESI): m/z 202.9/204.9 [M-OH]+.

The chemical industry reduces the impact on the environment during synthesis Methyl 4-bromo-2-chlorobenzoate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; SUZHOU CONNECT BIOPHARMACEUTICALS, LTD.; ZHENG, Wei; PAN, Wubin; YANG, Xin; (47 pag.)EP3048103; (2016); A1;,
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Reference of 478375-40-5, 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 478375-40-5 as follows.

AIBN (2,2′ -azobis(2-methylpropionitrile)) (1.79 g) was added to methyl 3-bromo-5-methylbenzoate (50 g) and N-bromosuccinimide (44.7 g) in 350 mL acetonitrile, and the mixture was35 refluxed overnight. An additional11 g of N-bromosuccinimide and 0.5 g of AIBN (2,2′ -azobis(2-methylpropionitrile)) was added, and the refluxing was continued for 3 hours. The mixture was concentrated, and then taken up in 500 mL ether, and stirred for 30 minutes. The mixture was thenfiltered, and the resulting solution was concentrated. The crude product was chromatographed onsilica gel using 10% ethyl acetate in heptane to give the title compound

According to the analysis of related databases, 478375-40-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ABBVIE INC.; BOGHAERT, Erwin, R.; JUDD, Andrew, S.; PHILLIPS, Andrew, C.; SOUERS, Andrew, J.; BRUNCKO, Milan; (503 pag.)WO2017/214301; (2017); 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. 24807-40-7, name is Methyl 3-(4-(benzyloxy)phenyl)propanoate, A new synthetic method of this compound is introduced below., Recommanded Product: 24807-40-7

To a solution of dimethyl methylphosphonate (1.16 g, 9.33 mmol) in THF (12.5 mL, 0.25 M) at -78 C was added nBuLi (3.9 mL, 9.33 mmol, 2.5 M in hexane). The mixture was stirred for 30 min after which a THF solution (2.5 mL) of ester 11 (750 mg, 3.10 mmol) was added slowly. The reaction mixture was warmed to RT and let stir for 1h, upon which time TLC indicated complete consumption of 11. The reaction mixture was quenched with saturated aqueous NH4Cl (5 mL). The mixture was diluted with H2O (10 mL) and extracted with EtOAc (4 x 25 mL). The combined organic layers were washed with H2O (50 mL), saturated aqueous NaCl (50 mL), dried over MgSO4, filtered, and concentrated in vacuo. Purification by FCC (EtOAc) yielded 12 (1.09 g, 3.01 mmol, 97%) as a clear oil. Data for 12: Rf 0.45 (1:1 Hexanes: EtOAc); IR (thin film) 3034, 2955, 1714, 1512, 1244 cm-1; 1H NMR (700 MHz, CDCl3) delta 7.44 (d, J = 7.5 Hz, 2 H), 7.39 (t, J = 7.6 Hz, 2 H), 7.34 (t, J = 8.6 Hz, 2 H), 6.91 (d, J = 8.6 Hz, 2 H), 5.05 (s, 2 H), 3.76 (d, J = 11.3 Hz, 6 H), 3.08 (d, J = 22.7 Hz, 2 H), 2.94 (t, J = 7.2 Hz, 2 H), 2.87 (t, J = 7.2 Hz, 2H); 13C NMR (176 MHz, CDCl3) delta 201.1, 157.2, 137.1, 132.9, 129.4, 128.6, 127.9, 127.5, 114.9, 70.0, 53.1 (d, J = 6.3 Hz), 45.8, 41.6 (d, J = 128.0 Hz), 28.6; HRMS (ESI) calcd for C19H24PO5 [M+H]: 363.1357, found 363.1361.

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:
Article; Salih, M. Quamar; Beaudry, Christopher M.; Tetrahedron Letters; vol. 58; 21; (2017); p. 2023 – 2025;,
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Reference of 148547-19-7, A common heterocyclic compound, 148547-19-7, name is Methyl 4-bromo-3-methylbenzoate, molecular formula is C9H9BrO2, 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 stirred solution of methyl 4-bromo-3-methylbenzoate (5g, 21.8 mmol) in dry 1 ,4- dioxane(100 ml_), were added dry Cs2CO3 (10.65 g, 32.7 mmol) and morpholine (2.3 g, 26 mmol). The mixture was degassed for 10 min. BINAP (0.67 g, 1.1 mmol) and palladium(ll)acetate (0.24 g, 1.1 mmol) were added under N2 and the resulting mixutre was refluxed for 15h. The reaction mixture was filtered through a pad of celite and the filtrate was evaporated. The crude product was purified by flash chromatography, affording the title compound as a yellow solid (4.3 g, 84%). 1H NMR (CDCI3, 400 MHz) delta 7.86-7.90 (m, 2H), 7.13-7.16 (d, 1 H), 3.98-4.0 (m, 4H), 3.91 (3H, s), 3.10-312 (m, 4H), 2.45 (3H, s). LC/MS (Method A): 236.0 (M+H)+. HPLC (Method B) Rt 2.24 min (Purity: 95.3%).

The synthetic route of 148547-19-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SERONO S.A.; WO2009/43889; (2009); A2;,
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Reference of 150529-73-0,Some common heterocyclic compound, 150529-73-0, name is Methyl 2-(3-bromophenyl)acetate, molecular formula is C9H9BrO2, 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 121A (2.28 g, 10.0 mmol) and N-bromosuccinimide (1.96 g, 11.0 mmol) in carbon tetrachloride (20 mL) was deoxygenated with a flow of nitrogen for 5 min. 2,2′-Azobisisobutyronitrile (82 mg, 0.5 mmol) was added and the mixture was refluxed for 18 h. Hexanes was added to the cooled mixture, and the resulting solid was filtered and washed with hexanes. The filtrate was concentrated on a rotary evaporator and then chromatographed (silica gel, step gradient from 100% hexanes to 5% ethyl acetate in hexanes) to give 121B (1.3 g, 42%) as clear oil. LC-MS m/z: 309.1 (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 Methyl 2-(3-bromophenyl)acetate, its application will become more common.

Reference:
Patent; Bristol-Myers Squibb Company; US2007/3539; (2007); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics