Tag: M.W=100-200

Reference of 24812-90-6, These common heterocyclic compound, 24812-90-6, name is Methyl 3-amino-4-methoxybenzoate, 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.

Anhydrous p-toluene sulfonic acid (20.99 g, 110.04 mmol) was melted at 120 C and 3-amino-4-methoxy benzoic acid methyl ester (10 g, 55.20 mmol) obtained in step 1 of Preparation Example 1 and 2,4-dichlorobenzonitrile (18.99 g, 110.04 mol) were added thereto and stirred at 180 C for 6 hours. The resulting solution was cooled to room temperature and the reaction was stopped by adding NaHCO3 thereto. The resulting mixture was extracted with ethyl acetate, the extract was dried over MgSO4 and concentrated under a reduced pressure. The concentrate was dissolved in 50 % methanol and 5 % NaOCl (30 ml, 20.64 mmol) was added dropwise thereto. After 5 min, the resulting mixture was extracted with ethyl acetate, the extract was dried over MgSO4 and concentrated under a reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent-MeOH/CDCl3=5:95, Merck, Silicagel 60) to obtain the title compound (18 g, 10.32 mmol) in a yield of 84 %. 1H NMR (CDCl3): delta 8.23 (1H, br), 7.75 (1H, d), 7.44 (1H, d), 7.36-7.26 (2H, m), 7.03 (1H, s), 6.88 (1H, d), 3.96 (3H, s), 3.76 (3H, s) MW: 318

Statistics shows that Methyl 3-amino-4-methoxybenzoate is playing an increasingly important role. we look forward to future research findings about 24812-90-6.

Reference:
Patent; CRYSTALGENOMICS, INC.; YUYU INC.; WO2004/65370; (2004); A1;,
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Synthetic Route of 394-35-4, A common heterocyclic compound, 394-35-4, name is Methyl 2-fluorobenzoate, molecular formula is C8H7FO2, 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.

N-(Pyrrolidin-3-yl methyl)-2-(4-chlorophenyl)-4-methylthiazole-5-carboxamide (168 mg, 0.500 mmol) and methyl 2-fluorobenzoate (0.127 mL, 1.00 mmol) were dissolved in dimethylsulfoxide (4 mL). To this solution, potassium carbonate (138 mg, 1.00 mmol) and tetrabutylammonium iodide (18.5 mg, 0.0500 mmol) were added and the mixture was stirred at 140°C for 6 hours. Subsequently, the reaction mixture was allowed to cool and water was added. The mixture was then extracted with ethyl acetate and the extract was washed with brine, followed by drying over magnesium sulfate and evaporation of the solvent. Purification of the resulting residue by silica gel column chromatography (hexane: ethyl acetate = 4:1 -> 2:1) gave 136 mg (58percent) of the desired compound as a colorless amorphous product. 1H NMR (400 MHz, CDCl3) delta 1.77-1.86 (1H, m), 2.11-2.19 (1H, m), 2.60-2.67 (1H, m), 2.71 (3H, s), 3.21-3.38 (4H, m), 3.54 (2H, t, J= 6.1 Hz), 3.87 (3H, s), 6.26 (1H, t, J = 6.1 Hz), 6.78 (1H, t, J = 7.9 Hz), 6.82 (1H, d, J = 8.6 Hz), 7.32-7.36 (1H, m), 7.41 (2H, d, J = 8.6 Hz), 7.63 (1H, dd, J = 1.8, 7.3 Hz), 7.85 (2H, d, J = 8.6 Hz). FAB+(m/z): 470 (M+H).

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:
Patent; KYORIN PHARMACEUTICAL CO., LTD.; EP1780210; (2007); A1;,
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These common heterocyclic compound, 2065-23-8, name is Methyl 2-phenoxyacetate, 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. category: esters-buliding-blocks

8.3 g of compound 2 was dissolved in 100 mL of methanol/water (9:1).12 g of lithium hydroxide was added. The reaction system was heated to 50 C and stirred for 12 h.The reaction was followed by TLC. After the reaction was over, the reaction system was added to 300 mL of ice water.Then, pH = 1 was adjusted with 6 mol/L HCl, and a large amount of white solid was formed. filter,A white solid was collected and dried in vacuo to give 6.8 g of white solid. The yield was 90%.

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

Reference:
Patent; Liaocheng University; Lei Kang; Chen Ke; Wang Shiben; Hua Xuewen; Liu Yang; Xu Xiaohua; (8 pag.)CN108570028; (2018); A;,
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Application of 924-99-2, A common heterocyclic compound, 924-99-2, name is Ethyl 3-(dimethylamino)acrylate, molecular formula is C7H13NO2, 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.

General procedure: Ethyl 4-(4-chlorophenyl)-2-thioxo-1,2,3,4-tertahydropyrimidine-5-carboxylate 6a (Table 2, entry 1). To a mixture of thiourea 12a (23.0 mg, 0.302 mmol), 4-chlorobenzaldehyde 13a (63.0 mg, 0.448 mmol), and ethyl 3-dimethylaminoacrylate 9 (64.0 mg, 0.447 mmol) in anhydrous DMF (0.3 mL) was added anhydrous aluminum chloride (8.0 mg, 0.0600 mmol) at room temperature, and the reaction mixture was stirred at 110 C for 3 h. To the mixture was added EtOAc (10 mL) and 1 M HCl aqueous solution (5 mL), and the organic layer was separated. The aqueous layer was extracted with EtOAc (10 mL), and the combined organic layers were washed with water (5 mL) and brine (5 mL), dried over anhydrous MgSO4, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography [n-hexane-EtOAc (4:1 to 2:1)] to give 6a (78.9 mg, 0.266 mmol, 88%) as pale yellow crystals.

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; Arai, Rie; Cho, Hidetsura; Gokurakuji, Yuki; Kikuchi, Hidetomo; Kubo, Takanori; Nakamura, Yuri; Nishimura, Yoshio; Sunaga, Katsuyoshi; Yuan, Bo; Tetrahedron Letters; (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. 816-27-3, name is Ethyl 2-ethoxy-2-iminoacetate, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C6H11NO3

To a solution of cyclopropanecarbohydrazide (6.9 g, 69 mmol, 1 equiv) in ethanol (20mL) was added ethyl 2-ethoxy-2-iminoacetate (10 g, 69 mmol, 1 equiv). The mixture was stirred at 40C overnight. The resulting solid was filtered and the filter cake was washed with cool ethanol to afford ethyl 2-(2-(cyclopropanecarbonyl)hydrazinyl)-2- iminoacetate as a white solid, which was used for next step without further purification(5.8 g, 42.7% yield). LC-MS: m/z 200.1 (M+H) +

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 816-27-3.

Reference:
Patent; ANNAPURNA BIO INC.; TANG, Haifeng; BOYCE, Sarah; HANSON, Michael; NIE, Zhe; (213 pag.)WO2019/169193; (2019); 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. 924-99-2, name is Ethyl 3-(dimethylamino)acrylate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: Ethyl 3-(dimethylamino)acrylate

b) Ethyl 3-(dimethylamino)-2-(2-fluoro-4-acetoxybenzoyl)-2-propenoate A stirred solution of Intermediate 12a (4.91 g) in DCM (80 mL) was treated with oxalyl chloride (3.25 mL) and dimethylformamide (2 drops). After 2 h the clear solution was evaporated and re-evaporated from DCM (2x). The acid chloride was re-dissolved in toluene (100 mL) and treated with triethylamine (5.17 mL) and ethyl 3- (dimethylamino)acrylate (4.13 g). After stirring for 2 h at 9O0C the mixture was cooled, filtered and the solution flash chromatographed (silica gel 40 to 100% EtOAc in petroleum ether [b.p. 40-600C]) to give the title compound as a white solid (4.3 g); APCI m/z 324.0 [M+H]+.

The synthetic route of 924-99-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; PLIVA-ISTRAZIVACKI INSTITUT D.O.O.; WO2006/50942; (2006); A1;,
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Application of 50413-30-4,Some common heterocyclic compound, 50413-30-4, name is Methyl 2-amino-4-methoxylbenzoate, molecular formula is C9H11NO3, 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.

Referential Example 23 3.1 mL of triethylamine and 1.3 mL of benzoyl chloride were added to 19 mL of methylene chloride solution containing 1.9 g of methyl 2-amino-4-methoxybenzoate while ice-cooled sequentially and stirred at room temperature for 3 hours. The solvent was evaporated under reduced pressure and chloroform and 1.0 mol/L hydrochloric acid were added to the obtained residue. The organic layer was separated and dried over anhydrous magnesium sulfate after washed with a saturated sodium hydrogen carbonate aqueous solution and a saturated sodium chloride aqueous solution sequentially, and the solvent was evaporated under reduced pressure. Hexane and diisopropyl ether were added to the obtained residue and a solid substance was separated by filtration to obtain 2.6 g of methyl 2-(benzamido)-4-methoxybenzoate as white solid. 1H-NMR (CDCl3) delta: 3.92 (3H, s), 3.93 (3H, s), 6.65 (1H, dd, J = 9.0, 2.7 Hz), 7.51-7.59 (3H, m), 8.00 (1H, d, H = 9.0 Hz), 8.05-8.07 (2H, m), 8.63 (1H, d, J = 2.7 Hz).

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-amino-4-methoxylbenzoate, its application will become more common.

Reference:
Patent; TOYAMA CHEMICAL CO., LTD.; EP1820795; (2007); A1;,
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Application of 58656-98-7, These common heterocyclic compound, 58656-98-7, name is tert-Butyl 4-fluorobenzoate, 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.

tert-butyl 4-(4-hydroxy-4-phenylpiperidin-1-yl)benzoate A solution of 4-hydroxy-4-phenyl piperidine (221 mg, 1.25 mmol) in DMSO (1 mL) was treated with tert-butyl-4-fluorobenzoate (196 mg, 1.00 mmol) and powdered potassium carbonate (173 mg, 1.25 mmol), stirred vigorously at 125 C. for 16 hours, cooled to room temperature, diluted with diethyl ether, washed with brine, dried (MgSO4), filtered, and concentrated to provide the desired product. MS (DCI(+)) m/e 354 (M+H)+.

Statistics shows that tert-Butyl 4-fluorobenzoate is playing an increasingly important role. we look forward to future research findings about 58656-98-7.

Reference:
Patent; Augeri, David J.; Baumeister, Steven A.; Bruncko, Milan; Dickman, Daniel A.; Ding, Hong; Dinges, Jurgen; Fesik, Stephen W.; Hajduk, Philip J.; Kunzer, Aaron R.; McClellan, William; Nettesheim, David G.; Oost, Thorsten; Petros, Andrew M.; Rosenberg, Saul H.; Shen, Wang; Thomas, Sheela A.; Wang, Xilu; Wendt, Michael D.; US2002/55631; (2002); A1;; ; Patent; Augeri, David J.; Baumeister, Steven A.; Bruncko, Milan; Dickman, Daniel A.; Ding, Hong; Dinges, Jurgen; Fesik, Stephen W.; Hajduk, Philip J.; Kunzer, Aaron R.; McClellan, William; Nettesheim, David G.; Oost, Thorsten; Petros, Andrew M.; Rosenberg, Saul H.; Shen, Wang; Thomas, Sheela A.; Wang, Xilu; Wendt, Michael D.; US2002/86887; (2002); 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. 5164-76-1, name is Dimethyl pent-2-enedioate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. SDS of cas: 5164-76-1

General procedure: The crude aryl diazonium tosylate 9 thus obtained was dissolved or suspended in MeOH (30 mL). Dimethyl glutaconate (1.45 mL, 10.0 mmol) and Pd(OAc)2 (112 mg, 0.5 mmol) were successively added while stirring. After stirring at r.t. for 15 h, the mixture was concentrated under reduced pressure and partitioned between CH2Cl2 (40 mL) and H2O (25 mL). The organic layer was washed with brine, dried (Na2SO4), and concentrated in vacuo. The residue was briefly fractionated on SiO2 using CH2Cl2 or CH2Cl2- acetone (5:1) as eluent. Fractions containing arylation product were pooled and concentrated to give compound 10 of at least 90% purity (according to 1H NMR analysis). It was used in the next step without further purification.

The synthetic route of 5164-76-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Dar’In, Dmitry; Kantin, Grigory; Bakulina, Olga; ?alubovskis, Raivis; Krasavin, Mikhail; Synthesis; vol. 51; 10; (2019); p. 2230 – 2236;,
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Electric Literature of 18448-47-0, 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. 18448-47-0, name is Methyl cyclohex-1-enecarboxylate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Step 1: Cyclohex-l-en-l-ylmethanol To a solution of methyl 1-cyclohexene-l-carboxylate (1.50 mL, 11.0 mmol) in DCM (30 mL) was added diisobutylaluminum hydride (1M solution in toluene; 25 mL, 25 mmol) at -78 C and the mixture was stirred for 1 h. TLC (3:1 hex:EtOAc) showed that the reaction was then complete. The mixture was quenched with methanol (10 mL) and IN NaOH (10 mL) and then was allowed to stir at rt for 2.5 h. The mixture was extracted with DCM (3x). The combined organic layers were washed with brine, dried over MgSCt, filtered and concentrated to give cyclohex-l-en-l-ylmethanol (1.3 g, 100%).

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 cyclohex-1-enecarboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MILLENNIUM PHARMACEUTICALS, INC.; DUFFEY, Matthew, O.; ENGLAND, Dylan, B.; HU, Zhigen; ITO, Mitsuhiro; LANGSTON, Steven, P.; MCINTYRE, Charles; MIZUTANI, Hirotake; XU, He; WO2015/2994; (2015); A2;,
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