Month: November 2020

Electric Literature of 4934-99-0, These common heterocyclic compound, 4934-99-0, name is Methyl 3-hydroxycyclobutanecarboxylate, 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 methyl 3- hydroxycyclobutanecarboxylate (2 g, 15.37 mmol), 5-methyl-4-nitro-lH-pyrazole (1 .95 g, 15.37 mmol) and PPh3 (6.05 g, 23.06 mmol) in THF (30 mL) was added dropwise DIAD (4.66 g, 23.06 mmol, 4.48 mL) at 0 C and degassed and purged with N2 for 3 times, and then the mixture was stirred at 25 C for 16 h under N2. The reaction mixture was concentrated under reduced pressure to remove THF. The residue was washed with PE:EtOAc (1 : 1, 30 mL), filtered and concentrated under reduced pressure to give a residue. The residue was purified by column chromatography (SiO?., PE:EtOAc =: 10: 1 to 5: 1) to give the mixture of trans-methyl 3-(5-methyi-4-nitro-pyrazol-l-yl)cyc3obutanecarboxylate and trans- methyl 3-(3-methy3-4~nitro-pyrazol~l -yl)cyclobutanecarboxylate as a white solid. LCMS: RT 0.729 min, m/z = 240,2 [M + H]+ To a solution of methyl 3-(5-methyi-4-nitro-py razol-l- yl)cyclobutanecarboxylate and methyl 3-(3-methyl-4-nitro-pyrazo3-l~yl)cyclobutanecarboxylate (1.7 g, 7.1 mmol, mixture) in MeOH (20 mL) was added NaBH4 (672 mg, 17.77 mmol) at 0 C. The mixture was stirred at 25 C for 2 h. The reaction mixture was quenched by addition of aq. NH4C1 (20 mL) at 0 C, and extracted with EtOAc (3 * 10 mL), washed with brine (5 mL), dried over Na SCX-i, filtered and concentrated under reduced pressure. The residue was purified by column chromatography (SiO?., PE:EtOAc = 5: 1 to 1 : 1) to give the mixture of trans- [3~(5-methyl-4-nitro~pyrazol-l~yl)cyclobutyl]methanol and fr n.v-[3-(3-methyl-4-nitro-pyrazol-l -yl)cyclobutyl]methanol as a yellow solid. LCMS: RT 0.645 min, m/z == 212.2 [M + H]+.

The synthetic route of 4934-99-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DENALI THERAPEUTICS INC.; ESTRADA, Anthony A.; FENG, Jianwen A.; LYSSIKATOS, Joseph P.; SWEENEY, Zachary K.; DE VICENTE FIDALGO, Javier; (271 pag.)WO2017/87905; (2017); A1;,
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Related Products of 1128-00-3,Some common heterocyclic compound, 1128-00-3, name is Ethyl 2-aminocyclohex-1-enecarboxylate, molecular formula is C9H15NO2, 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 170 mg of ethyl 2-aminocyclohex-1-enecarboxylate as synthesized in Step 7-1-B in 5 ml of pyridine, 70 mg of phosphorus trichloride was added under cooling with ice, followed by 15 minutes’ stirring. Raising the temperature to room temperature, 327 mg of 5-(4-quinoline-2-ylpiperazin-1-yl)hexanoic acid as synthesized in above Step 7-14-C was added to the solution and stirred for 3 hours. Distilling the pyridine off under reduced pressure, the residue was extracted with ethyl acetate and washed with water. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was concentrated under reduced pressure. The residue was purified on silica gel column chromatography (ethyl acetate) to provide 182 mg (38%) of ethyl 2-[5-(4-quinolin-2-ylpiperazin-1-yl)hexanoylamino]cyclohex-1-enecarboxylate. 1H-NMR(CDCl3)delta:11.61(br s,1H),7.86(d,J=8.9Hz,1H), 7.68(d,J=8.5Hz,1H),7.57(d,J=7.7Hz,1H), 7.51(ddd,J=1.2Hz,6.9Hz,8.1Hz,1H),7.22~7.18(m,1H), 6.96(d,J=9.3Hz,1H),4.14(q,J=6.9Hz,2H),3.80~3.70(m,4H), 2.98~2.95(m,2H),2.75~2.65(m,3H),2.64~2.56(m,2H), 2.34(t,J=7.3Hz,2H),2.31~2.28(m,2H),1.81~1.70(m,2H), 1.69~1.56(m,6H),1.26(t,J=6.9Hz,3H),1.01(d,J=6.6Hz,3H) Mass,m/e:478(M+),157(base)

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

Reference:
Patent; ASKA Pharmaceutical Co., Ltd.; EP1724267; (2006); A1;,
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6933-47-7, name is Methyl 4-amino-2-methylbenzoate, 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. SDS of cas: 6933-47-7

A solution of 3,5-dichloro-4-ethoxybenzoic acid (1) (285 mg, 1.21 mmol) and DIPEA (1.05 mL, 6.05 mmol) in DMF (2.5 mL) was added to HATU (690 mg, 1.82 mmol) and the orange mixture was stirred for 5 min prior to the addition of methyl 4-amino-2-methylbenzoate (2) (200 mg, 1.21 mmol) in DMF (1 mL). The resulting dark orange solution was stirred overnight for 18 h. 2 M HCl (10 mL) was added and stirring continued for 10 min, and then the mixture was extracted with diethyl ether. The organic layer was washed with water (3*15 mL), dried over MgSO4, filtered and the solvent was evaporated in vacuo. The yellow residue was purified by silica gel chromatography (40 g, 0-100% EtOAc in isohexane) to afford methyl 4-(3,5-dichloro-4-ethoxybenzamido)-2-methylbenzoate (3) (267 mg, 56%): m/z 380 (M-H)- (ES-). 1H NMR (400 MHz, CDCl3) delta: 7.97 (1H, s), 7.80 (3H, m), 7.54 (1H, dd), 7.51 (1H, d), 4.18 (2H, q), 3.89 (3H, s), 2.63 (3H, s), 1.49 (3H, t).

The synthetic route of 6933-47-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KING’S COLLEGE LONDON; US2012/149737; (2012); A1;,
Ester – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 685-88-1, name is Diethyl 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 685-88-1, COA of Formula: C7H11FO4

Diethyl 2-fluoromalonate (5 g, 28.1 mmol) was added, over 10 min, to a stirred suspension of sodium hydride (1.347 g, 33.7 mmol) in tetrahydrofuran (50 mL) at 0C and the resulting colourless solution was stirred at 0 C for 15 min. and then at RT for 30 min. The solution was cooled to 0 C, a solution of 6-bromohex-l-ene (4.58 g, 28.1 mmol) in THF (20 mL) was then added over 5 min. and the resulting reaction mixture was heated to 60 C and stirred for 16 h. Then the reaction mixture was cooled to 0 C, quenched with ice cold water (100 mL) and extracted with ethyl acetate (2 x 200 mL). The combined organic layer was washed with water (200 mL), brine (200 mL), dried over anhydrous sodium sulphate, filtered and the filtrate concentrated under reduced pressure. The crude product was purified by combiflash chromatography (80 g Redisep S1O2 column, eluting with 10 % EtOAc in n- hexanes) to afford the title compound 162A (5 g, 68%) as a colourless oil. LC-MS retention time = 3.30 min; m/z = 261.2 [M+H]+ KINETIX XB-C18, (75 X 3) mm, 2.6 micron column; Flow rate: 1 mL/min; Mobile Phase A: 10 mM HCO2NH4 in 98% Water/ 2% ACN; Mobile Phase B: 10 mM HCO2NH4 in 2% Water/ 98% ACN; 20% B to 100% B over 4.6 min, then hold 0.4 min. at 20% B with flow rate 1.5 mL/min; Detection: UV at 220 nm. NMR (400MHz, CDCh) delta ppm 5.78 (ddt, J=17.1 , 10.3, 6.6 Hz, 1H), 5.01 (d, J=17.2 Hz, 1H), 4.95 (d, J=6.4 Hz, 1H), 4.34 (q, J=5.6 Hz, 4H), 2.18 – 2.05 (m, 4H), 1.43 – 1.40 (m, 4H), 1.30 (t, J=7.2 Hz, 6H).

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, Diethyl fluoromalonate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; DEVASTHALE, Pratik; MOORE, Fang; ZHAO, Guohua; PIENIAZEK, Susan Nicole; SELVAKUMAR, Kumaravel; DHANUSU, Suresh; PANDA, Manoranjan; MARCIN, Lawrence R.; (384 pag.)WO2018/89355; (2018); A1;,
Ester – Wikipedia,
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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. 4891-38-7, name is Methyl Phenylpropiolate, A new synthetic method of this compound is introduced below., Safety of Methyl Phenylpropiolate

General procedure: A reaction kettle (30 mL) was charged with aniline (1.0 mmol), and alkyne ester (1.0 mmol). The mixture was stirred at room temperature for 10 minutes, then added terminal alkyne (1.2 mmol, 1.2 eq), AgOTf (5 mol%, 12.9 mg), HOTf (10 mol%, 15 mg), MeOH (2 mL) in the mixture. The mixture was stirred at 120 oC for 24 hours, the mixture was quenched by sat. aq. NaHCO3, and diluted with 20 mL of dichloromethane and washed with 10 mL of H2O. The aqueous layer was extracted twice with dichloromethane (10 mL) and the combined organic phase was dried over Na2SO4. After evaporation of the solvents, the residue was purified by silica gel chromatography (hexane/AcOEt = 5:1) to afford quinoline derivatives. All other compounds are synthesized in a similar manner, with the yields listed in the main text calculated from the isolated, pure products.

The synthetic route of 4891-38-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Li, Yunlan; Zhang, Qiurui; Xu, Xuefeng; Zhang, Xu; Yang, Yurong; Yi, Wei; Tetrahedron Letters; vol. 60; 14; (2019); p. 965 – 970;,
Ester – Wikipedia,
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These common heterocyclic compound, 62451-84-7, name is Methyl 2-(3-(trifluoromethyl)phenyl)acetate, 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. SDS of cas: 62451-84-7

EXAMPLE 98; 4-[2-Methoxy-1-(3-trifluoromethyl-phenyl)-ethyl]-piperazine-1-carboxylic acid (7-methoxy-thiazolo[5,4-d]pyrimidin-2-yl)-amide; Step 1: A mixture of (3-trifluoromethyl-phenyl)-acetic acid methyl ester (6.0 g, 25.9 mmol) and N-bromosuccinimide (9.2 g, 51.7 mmol) and a few drops of hydrobromic acid (48% solution) in chloroform (250 mL) was heated under reflux for two days. The reaction mixture was concentrated to dryness, taken up in methylene chloride and loaded onto a column of silica gel. Elution with 5% ethyl acetate/hexanes gave Bromo-(3-trifluoromethyl-phenyl)-acetic acid methyl ester (3.0 g, 39% yield) as colorless oil. The NMR spectrum obtained on the sample is compatible with its structure.

The synthetic route of Methyl 2-(3-(trifluoromethyl)phenyl)acetate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Brinkman, John A.; Cheung, Adrian Wai-Hing; Firooznia, Fariborz; Guertin, Kevin Richard; Marcopulos, Nicholas; Qi, Lida; Racha, Jagdish Kumar; Sarabu, Ramakanth; Tan, Jenny; Tilley, Jefferson Wright; US2007/270433; (2007); A1;,
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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. 34846-90-7, name is Methyl 3-methoxyacrylate, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 34846-90-7

EXAMPLE 2 The toluene solution of 3-mercapto-2-butanone from the previous step (613 g of ca. 25 wt percent solution) was placed in a clean, dry reactor along with 15 g of methyl-3-methoxyacrylate. The mixture was warmed to 25¡ã C., stirred vigorously, and treated with solid sodium methoxide (8.5 g, ca. 0.1 equiv.) all at once. The remaining methyl-3-methoxyacrylate (151 g) was added in at a rate to keep the temperature at or below 35¡ã C. (2 h). The resulting mixture was allowed to reach room temperature and stir for 21 h. Concentrated hydrochloric acid (88 g) was added to the mixture over 30 min such that the temperature did not exceed 35¡ã C. The resulting mixture was stirred vigorously for 2 h, then treated with 73 g of water, and stirred for 10 min more. The phases were allowed to separate. After standing for 10 min, the aqueous phase was drained from the reactor, and the upper, product phase was washed with 100 g of 5percent sodium bicarbonate solution. After being stirred for 15 min, the phases were allowed to separate. The lower, aqueous phase was drained from the reactor, and the upper, product phase was transferred to a distilling flask. The toluene was distilled through a 5-plate distillation column at 100 mmHg. After a small fraction containing toluene and other low boiling impurities was collected, the product, 3-carbomethoxy-4,5-dimethylthiophene, was distilled through the column at 50 mmHg.

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 34846-90-7.

Reference:
Patent; Monsanto Company; US6037478; (2000); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 619-42-1, The chemical industry reduces the impact on the environment during synthesis 619-42-1, name is Methyl 4-bromobenzoate, I believe this compound will play a more active role in future production and life.

Eth nytfime hyisfiane (82.4 g, 0,84 mol) was added dropwise over 10 min under a nitrogen atmosphere to a solution of methyl 4-bromobenzoate (150 g, 0.7 mol), PdC (PPh3)2 (15 g, 0.021 mol) and Cu (13 g, 0.07 mol) in TEA (1.5 L) and the reaction was siirsd at 90 for 30 minutes. Solids were collected by filtration and washed with EtOAc (5 x 500 mL). The filtrate was concentrated under reduced pressure to give a residue, which was distilled under reduced pressure to yield methyl 4-C(trimethylsify) ethynyl) benzoate (INT-12) as an off-white solid (156 g, 96%),

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

Reference:
Patent; ACHAOGEN, INC.; PATTERSON, Brian D.; LU, Qing; AGGEN, James Bradley; DOZZO, Paola; KASAR, Ramesh Annasaheb; LINSELL, Martin Sheringham; KANE, Timothy Robert; GLIEDT, Micah James; HILDEBRANDT, Darin James; MCENROE, Glenn A.; COHEN, Frederick; WO2013/170165; (2013); A1;,
Ester – Wikipedia,
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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. 454-31-9, name is Ethyl 2,2-difluoroacetate, A new synthetic method of this compound is introduced below., Recommanded Product: 454-31-9

Intermediate 6 (53.35 g, 0.22 mol) was stirred in toluene (1500 mL) at 0 C under N2. Potassium tert-butoxide (34.14 g) was added at 0-5 C and 2,2-difluoro-acetic acid ethyl ester (33.01 g, 0.27 mol) was added dropwise at 0-5 C. The RIVI was stirred at RT for 2 h, then washed with 10% H2S04 in water and the OL was dried on MgSO4,filtered and evaporated, yielding intermediate 7 (70.50 g, quantitative).

The synthetic route of 454-31-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; VAN ROOSBROECK, Yves, Emiel, Maria; BUIJNSTERS, Peter, Jacobus, Johannes, Antonius; TRESADERN, Gary; JACOBY, Edgar; OEHLRICH, Daniel; GIJSEN, Henricus, Jacobus, Maria; (67 pag.)WO2018/83103; (2018); A1;,
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Electric Literature of 5941-55-9, 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. 5941-55-9, name is Ethyl (E)-3-Ethoxyacrylate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of (E)-ethyl 3-ethoxyacrylate (12.6 g, 87.6 mmol) in 1,4-dioxane (50 mL) and water (50 mL) was added NBS (17.2 g, 96.4 mmol) at 0C. The mixture was stirred for 1 hour at room temperature. Benzothioamide (12.1 g, 87.6 mmol) was added and the mixture was stirred for 1 hour at 80-90C. The reaction mixture was cooled down to room temperature and poured into NH4OH (300 mL, 3% in water) and extracted with ethyl acetate (150 mL x 2), dried over sodium sulfate, concentrated and purified by chromatography (PE:EA =10/1) to give compound 10-la (2.9 g, 14% yield); LCMS (ESI): m/z 234 [M+Hf?.

The synthetic route of Ethyl (E)-3-Ethoxyacrylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TUFTS UNIVERSITY; HAYDON, Philip, G.; LEE, Jinbo; (160 pag.)WO2018/58148; (2018); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics