Tag: M.W=100-200

Some common heterocyclic compound, 25415-67-2, name is Ethyl 4-methylpentanoate, molecular formula is C8H16O2, 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. category: esters-buliding-blocks

EXAMPLE 37 (FROM TABLE 1) 5-Bromo-2-oxo-1,2-dihydroindol-3-ylidenemethyl)-2-isopropyl-4-phenyl-1H-pyrrole-3-carboxylic Acid (3-diethylaminopropyl)amide A mixture of 2-aminoacetophenone hydrochloride (1 equiv.), ethyl isobutylacetate (1.2 equiv.) and sodium acetate (2.4 equiv.) in H2O was stirred at 100 C. for 18 hours and then cooled to room temperature. The aqueous layer was decanted off and the oil was dissolved in ethyl acetate. It was then washed with water and brine and then dried to give (93%) of 2-isopropyl-4-phenyl-1H-pyrrole-3-carboxylic acid ethyl ester as a red brown oil. 1H NMR (300 MHz, DMSO-d6) delta 11.21 (s, br, 1H, NH), 7.14-7.27 (m, 5H), 6.70 (d, J=2.7 Hz, 1H), 4.02 (q, J=7.1 Hz, 2H, OCH2CH3), 3.65 (m, 1H, CH(CH3)2), 1.22 (d, J=7.5 Hz, 6H, CH(CH3)2), 1.04 (t, J=7.1 Hz, 3H, OCH2CH3). MS-EI m/z 257 [M+].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 25415-67-2, its application will become more common.

Reference:
Patent; Sugen, Inc.; US6878733; (2005); B1;,
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Application 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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Synthetic Route of 28868-76-0, A common heterocyclic compound, 28868-76-0, name is Dimethyl 2-chloromalonate, molecular formula is C5H7ClO4, 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 suspension of K2CO3 (49.3 G) in acetone (100 ml) a solution of 2-chloro-5- methoxy-phenol (37.7 G, boiling point 83-86C, 13 mbar, [9]) was added dropwise at 40C. The dropwise addition of dimethyl CHLOROMALONATE (43.6 G) in acetone (100 ml) followed. The mixture was refluxed for 16 h before the solvent was removed under reduced pressure. The residue was taken up in water (400 ML) and extracted twice with DCM (400 ML). The organic extracts were dried over MGS04 and evaporated. Upon treatment of the oily residue with diethyl ether, the product crystallised. The crystals were collected, washed with a mixture of diethyl ether and hexane and dried to give 2- (2-chloro-5-methoxy-phenoxy)-malonic acid dimethyl ester (53.73 g) as white crystals. (CDC13) : 3.76 (s, 3H), 3.86 (s, 6H), 5.20 (s, 1 H), 6.53-6. 58 (m, 2H), 7.24-7. 29 (m, 1 H).

The synthetic route of 28868-76-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; WO2004/50640; (2004); A1;,
Ester – Wikipedia,
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Related Products 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;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 394-35-4, 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. 394-35-4 name is Methyl 2-fluorobenzoate, 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.

General procedure: Compounds 6a-t were synthesized from substituted benzoic acid via six steps according to the literature method as described. Various substituted benzoic acids 1a-t were treated with SOCl2 to give compounds 2a-t, which were reacted with CH3OH and EtN3 in CH2Cl2 at 0 to afford compounds 3a-t. Compounds 4a-t were prepared by the reaction of compounds 3a-t, hydrazine hydrate in CH3OH under reflux condition about 5h. Subsequently, compounds 5a-t were obtained by reaction of compounds 4a-t with CS2 and KOH in CH3OH. Compounds 6a-t were obtained by the cyclization reaction of compounds 5a-t in the presence of HCl at 0-5°C.

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

Reference:
Article; Li, Liangjing; Ding, Hao; Wang, Baogang; Yu, Shichong; Zou, Yan; Chai, Xiaoyun; Wu, Qiuye; Bioorganic and Medicinal Chemistry Letters; vol. 24; 1; (2014); p. 192 – 194;,
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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. 394-35-4, name is Methyl 2-fluorobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C8H7FO2

A mixture of 20.0 g of methyl 2-fluorobenzoate, 15.2 g of methyl thioglycolate, 21.8 g of potassium carbonate,and 150 ml of N,N-dimethylformamide was stirred for 4 hours at 60°C. After the reaction mixture was cooled to roomtemperature, water was added thereto, and the residue was washed three times with tert-butyl methyl ether. Concentratedhydrochloric acid was added to the aqueous layer, and then extraction was performed three times by using tert-butylmethyl ether. The collected organic layer was washed with water and saturated saline, dried over magnesium sulfate,and then concentrated under reduced pressure. The residues were recrystallized from ethanol and water, therebyobtaining 3.89 g of methyl 3-hydroxybenzo[b]thiophene-2-carboxylate.

The synthetic route of 394-35-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sumitomo Chemical Company Limited; MUKUMOTO, Fujio; TAMAKI, Hiroaki; KUSAKA, Shintaro; IWAKOSHI, Mitsuhiko; EP2926660; (2015); A1;,
Ester – Wikipedia,
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57486-67-6, name is Methyl 2-(2-fluorophenyl)acetate, 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. Quality Control of Methyl 2-(2-fluorophenyl)acetate

EXAMPLE 4 4-[(R,S)-2-(2-Fluorophenyl),propyl]-1-{(R,S)-2-fluoro-3-[5-(1,2,4-triazol-4-yl)-1H-indol-3-yl]propyl}pipeperazine Methyl 2-fluorophenylacetate (24.2 g, 0.144 mol) in THF (75 ml) was added dropwise over 20 min to a -78 C. solution of LDA (diisopropylamine (16.0 g, 0.158 mol) and n-butyl lithium (2.5 M, 61 ml)) in THF (300 ml) and stirring was continued for 1 h. Methyl iodide (22.5 g, 0.158 mol) was added dropwise over 15 min and the reaction mixture allowed to warm to room temperature over 1 h. The solution was poured into saturated ammonium chloride solution and extracted with diethyl ether. The extract was washed with brine, dried and evaporated to yield methyl 2-(2-fluorophenyl)propanoate (26.2 g, 100%) as an oil.

The synthetic route of 57486-67-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck Sharp & Dohme Ltd.; US5977116; (1999); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 64113-91-3, name is tert-Butyl 2-aminobenzoate, 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 64113-91-3, Recommanded Product: tert-Butyl 2-aminobenzoate

To a solution of [4- (PHENYLMETHYL) PHENYL] acetic acid (0.059g, 0. 26MMOL, 1 EQUIV) and DIPEA (0. 054ML, 0. 31MMOL, 1.2equiv) in anhydrous DMF (0. 5MOI) was added a solution of HATU (0.119g, 0. 31MMOL, 1.2equiv) in DMF (0. 5M1), FOLLOWED by 1,1- dimethylethyl 2-aminobenzoate (0.060 g, 0. 31mmol, 1.2equiv) in DMF (0. 5ml). The mixture was stirred under an atmosphere of nitrogen for 72 hr, then concentrated under reduced pressure and partitioned between DCM and 2N HCI. The separated organic phase was washed with saturated sodium bicarbonate then evaporated under a stream of nitrogen and purified by preparative h. p. l. c. to give the title compound (0.033g, 32%) as a white solid ; LC/MS : m/z 402.2 [MH] +.

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

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2005/16870; (2005); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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 394-35-4 as follows. category: esters-buliding-blocks

0.06 mol of methyl o-fluorobenzoate,0.022 mol DIC,6.6 mmol DMAP was added to 100 mL dichloromethane, Stirring to continue stirring at room temperature for 30min,Gradually warming to 45 ~ 50 ,The reaction flask was charged with 1-cyclopropanecarbonylpiperazine (0.08 mol)Continue stirring reaction 9 ~ 10h.After the reaction is completed,Cool to 0 C and stir 45min,filter,The filtrate was washed with water (3 * 50 mL)Dried over anhydrous sodium sulfate,The methylene chloride was evaporated under reduced pressure,Got solid,Compound 2 (15.27 g),The yield is 92.57%.

According to the analysis of related databases, 394-35-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Shandong Yuxin Pharmaceutical Co., Ltd.; Liu Zhenteng; Sun Yiwei; Li Zhen; Xu Guichao; Leng Xiangxiang; Huang Chunyan; (9 pag.)CN107266370; (2017); A;,
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. 89-91-8, name is Methyl 2,2-dimethoxyacetate, A new synthetic method of this compound is introduced below., Application In Synthesis of Methyl 2,2-dimethoxyacetate

EXAMPLE 6 2,2-Dimethoxy-N-(3,4-dimethoxybenzyl)-acetamide 16.7 g. (0.1 mole) 3,4-dimethoxybenzylamine are contacted with 13.4 g. (0.1 mole) methyl 2,2-dimethoxyacetate for 3 hours. The reaction mass solidifies. The crude product is recrystallized from about 1 liter of a light petroleum ether fraction to give 19.4 g. of 2,2-dimethoxy-N-(3,4-dimethoxybenzyl)-acetamide in the form of white needles. A sample intended for analysis is sublimed at 70 C./0.03 mm.Hg. The yield is 72% of theory. The product has a melting point of 60 C. Infrared spectroscopy (CCl4) (cm-1): 3440 (NH), 2950 (CH3), 2850 (OCH3), 1680 + 1510 (CONH), 1600, 1460, 1115 + 1070 (CO) NMR (CDCl3): 6.84 (4H, singlet, Ha); 4.72 (1H, singlet, Hb); 4.38 (2H, doublet, Hc, J=6Hz); 3.87 (6H, singlet, Hd); 3.39 (6H, singlet, He) STR11 Mass spectrum: m/e 269 (M+), 237 (–CH3 OH), 222, 206 (M* at 209), 181, 166 (amine), 151 (tropylium), 75, 47, 31 (M* at 29.5) Analysis: C13 H19 NO5 (M.W. 269.3): calculated: C 57.98%; H 7.11%; N 5.20%; found: 57.95%; 7.15%; 5.17%

The synthetic route of 89-91-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; U C B, Societe Anonyme; US4041077; (1977); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics