Month: December 2020

These common heterocyclic compound, 66315-16-0, name is Methyl 3-amino-4-(methylamino)benzoate, 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

DCC (12.3 g, 59.7 MMOL) was added to an ice-water cooled solution of N-BOC 8-alanine (10.0 g, 52.8 MMOL) and methyl 3-amino-4-methylaminobenzoate (8.27 g, 45.9 MMOL) in CH2CI2 (400 mL). The reaction mixture was stirred 1 h at 0C and overnight at room temperature, then the insoluble urea was removed by filtration. After concentration, the residue was dissolved in ethyl acetate and washed with 5% NAHCO3, followed with saturated NaCl. The organic solution was dried over NA2SO4, concentrated, and purified by chromatography over silica gel eluted with 1: 2 hexane-EtOAc to afford 15.02 g (93%) of desired product as a white SOLID. 1H NMR (300 MHz, D6-DMSO) o 9.06 (s, 1H), 7.70 (d, J=1.8 Hz, 1 H), 7.66 (dd, J=8.4 Hz, J=1.8 Hz, 1 H), 6.87 (s, 1 H), 6.59 (d, J=8.4 Hz, 1 H), 5.89 (d, J=4.8 Hz, 1 H), 3.74 (s, 3H), 3.23 (q, J=6.9 Hz, 2H), 2.76 (d, J=4.8 Hz, 3H), 2.46 (t, J=6.9 Hz, 2H), 1.38 (s, 9H). Anal. Calc’d. FORC17H25N305 : C, 58.11 ; H, 7.17 ; N, 11.96. Found: C, 58.28 ; H, 7.09 ; N, 11.92.

The synthetic route of Methyl 3-amino-4-(methylamino)benzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PHARMACIA CORPORATION; WO2004/99131; (2004); A2;,
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Reference of 6962-92-1, These common heterocyclic compound, 6962-92-1, name is 4-Chlorobutyl 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.

Preparation 6 To an ice-cooled solution of 3-(3-oxo-2,3-dihydropyridazin-6-yl)-2-phenylpyrazolo[1,5-a]pyridine (2.0 g) in N,N-dimethylformamide (20 ml) was added portionwise sodium hydride (60% dispersion in mineral oil; 0.31 g). After addition was finished, the mixture was stirred for 15 minutes in an ice-bath. To this mixture was added 4-chlorobutyl acetate (1.1 g), and the reaction mixture was stirred for 24 hours at room temperature, and then for 36 hours at 70 C. After being cooled to room temperature, the reaction mixture was concentrated. The residue was partitioned between ethyl acetate and water. The organic layer was separated and the aqueous layer was extracted twice with ethyl acetate. The combined organic layers were washed with water and sodium chloride aqueous solution, dried over anhydrous magnesium sulfate, and concentrated. Purification of the residue by column chromatography on silica gel (using 3:1 mixture of chloroform and ethyl acetate as eluent) gave 3-[2-(4-acetoxybutyl)-3-oxo-2,3-dihydropyridazin-6-yl]-2-phenylpyrazolo[1,5-a]pyridine (2.6 g). An analytical sample was prepared by recrystallization from diisopropyl ether. mp: 102-103 C. IR (Nujol): 1720, 1660 cm-1 NMR (CDCl3, delta): 1.7-1.9 (2H, m), 1.9-2.2 (2H, m), 2.05 (3H, s), 4.16 (2H, t-like, J=ca. 6Hz), 4.31 (2H, t-like, J=ca. 6Hz), 6.77 (1H, d, J=10Hz), 6.8-7.0 (1H, m), 7.02 (1H, d, J=10Hz), 7.2-7.4 (1H, m), 7.4-7.5 (3H, m), 7.6-7.7 (2H, m), 7.9-8.0 (1H, m), 8.5-8.6 (1H, m) MASS m/z: 402, 343, 287 Anal. Calcd. for C23 H22 N4 O3: C 68.64, H 5.51, N 13.92 (%) Found: C 68.31, H 5.48, N 13.76 (%)

The synthetic route of 6962-92-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Fujisawa Pharmaceutical Co., Ltd.; US5338743; (1994); A;,
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Related Products of 653-92-9, 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 653-92-9 as follows.

(b) Methyl 2-cyano-4-fluorobenzoate; Methyl 2-bromo-4-fluorobenzoate (1.0 g, 4.29 mmol; see step (a) above) was dissolved in dry DMF (5 mL) and degassed with N2-gas for 5 minutes. CuCN (769 mg, 8.58 mmol) was added and mixture was degassed again before the temperature was raised. The reaction mixture was refluxed for 75 minutes. NaCN (aq, 10%) was added and the mixture was extracted with DCM. The DCM phase was dried through a phase separator and the solvent was removed in vacuo. The crude product was dissolved in toluene and washed once with water. The organic phase was dried over MgS04 and filtered. The solvent was removed in vacuo to give the product (in 94% yield), which was used without further purification. ‘H NMR (500 MHz, CDC13) 5 4.01 (s, 3H), 7.35-7. 42 (m, 1H), 7.52 (dd, 1H), 8.15-8. 23 (m, 1H)

According to the analysis of related databases, 653-92-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTRAZENECA AB; WO2005/58826; (2005); A1;,
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Synthetic Route of 3469-00-9,Some common heterocyclic compound, 3469-00-9, name is Methyl Diphenylacetate, molecular formula is C15H14O2, 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 diisopropylamine (0.17 mL, 1.19 mmol) in THF (1 mL) was added n-BuLi (2.5 M in hexane, 0.4 mL, 0.994 mmol) at -78 C. The reaction mixture was stirred at this temperature for 30 min, followed by stirring at -5 C for 30 min. Then, the reaction mixture was cooled to -78 C and diphenyl methylacetate (S6) (0.15 g, 0.66 mmol) in THF (2 mL) was added. After stirring at -78 C for 15 min, (E)-4,6-iodoheptadiene (S11) (0.16 g, 0.72 mmol) was added. The resulting solution was stirred at rt overnight. The reaction mixture was quenched with satd aq NH4Cl (10 mL) and extracted with EtOAc (2 x 50 mL). The extract was washed with water and brine, dried (MgSO4), filtered, and concentrated by rotary evaporation. Column chromatography of the residue (20:1 hexane/EtOAc) gave S12 (120 mg, 63%) as colorless oil.

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

Reference:
Article; Chandrasekhar; Ryu, Jae-Sang; Tetrahedron; vol. 68; 24; (2012); p. 4805 – 4812;,
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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 4630-80-2 as follows. Formula: C7H12O2

General procedure: A solution of 1.02 mL (19.49 mmol) of acetonitrile in 13 mL of THF was cooled to 0 C and added 11.4 mL (19.49 mmol) of potassiumt-pentoxide solution (1.7 M in toluene) dropwise with constant stirring. The reaction mixture was stirred at room temperature for 2h. Reaction mixture was cooled again to 0 C and 1.32 g (9.74 mmol) of methyl benzoate was added dropwise followed by stirring for additional 2h at room temperature. After completion of the reaction (by TLC), crude mixture was quenched with 1NHCland extracted with ethyl acetate. The organic layer was washed with brine and dried over MgSO4. The crude was purified with column chromatography using hexane and ethyl acetate eluent to yield 0.56 g (40%) 3-oxo-3-phenylpropanenitrile.

According to the analysis of related databases, 4630-80-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Rana, Sandeep; Sonawane, Yogesh A.; Taylor, Margaret A.; Kizhake, Smitha; Zahid, Muhammad; Natarajan, Amarnath; Bioorganic and Medicinal Chemistry Letters; vol. 28; 23-24; (2018); p. 3736 – 3740;,
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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 72338-48-8 as follows. category: esters-buliding-blocks

2.98 g of amantadine was dissolved in 15 mL of DMF, and 5.5 g of ethyl bromododecanoate and 4.9 g of K2CO3 were added.Reaction at 60 C for 16 hours;Then diluted with 100 mL of water and extracted with ethyl acetate (3¡Á50 mL);After the organic phase is combined, it is dried with sodium, and then the solid is filtered off.The filtrate is concentrated in vacuo and purified to give a yellow oil, 12-(adamantyl)aminododecanoate;

According to the analysis of related databases, 72338-48-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; China Agricultural University; Wang Zhanhui; Jiang Haiyang; Wen Kai; Shen Jianzhong; Zhang Xiya; Chen Chaochao; Duan Changfei; Yu Wenbo; Yu Xuezhi; (17 pag.)CN110105232; (2019); A;,
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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. 1236357-65-5, name is Methyl 1-(4-bromophenyl)cyclobutanecarboxylate, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C12H13BrO2

To a 25 mL round-bottom t1ask purged with and maintained under an inertatmosphere of nitrogen was added (1 S,4S,5R)-.5-[ [ 5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2- oxazol-4-yl]methoxy ]-2-az.abicyclo[ 2.2.l]heptane hydroiodide salt l2dd (200 mg, 0.3943rnmol, 1.00 equiv.), Tol (lO mL), methyll-(4-bromophenyl)cyclobui:me-1-carboxylate 150b(212 mg, 0.79 mmol, 2.0 equiv.), Ru-Phos-Precatalyst (89 mg, 0.10 mmol, 0.25 equiv.),RuPhos (89 mg), and Cs2C01 (516 mg, 1.58 mmol, 4.00 equiv.). The resulting mixture was5 stirred at ll 0 C overnight and concentrated under vacuum. The residue vvas puriiled bysilica gel column chromatography eluting with ethyl acetate/petroleum ether (l/5) to affordmethyl 1-[4-[ (l S,4S,5R)-5-[ [ 5-cyclopropyl-3-(2,6-dichlorophenyl)- L2-oxazol-4-y l]methoxy ]-2-azabicydo[2.2.1]heptan-2-yl]pheny l]cyclobutane-1-carboxy late 150c (140rng, 63~”0) as a light yellow oil.

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 1236357-65-5.

Reference:
Patent; ARDELYX, INC.; CHAO, Jianhua; JAIN, Rakesh; HU, Lily; LEWIS, Jason Gustaf; BARIBAULT, Helene; CALDWELL, Jeremy; (582 pag.)WO2018/39386; (2018); A1;,
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Related Products of 403-33-8, A common heterocyclic compound, 403-33-8, name is Methyl 4-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.

General procedure: Various benzohydrazides 5-7 and 9-13 were obtained accordingto known procedures [40,65] except for benzohydrazides 4and 8 which were commercially available. A solution of the methylbenzoate (1 equiv) in ethanol was added dropwise to 65% hydrazinemonohydrate (5 equiv). The reaction mixture was then heatedunder reflux and stirred overnight. The reaction progress was followedup by TLC. Crude product was collected by filtration aftercooling of the reaction medium and finally washed with coldethanol unless specified otherwise. The desired benzohydrazides were used without any further purification.The analysis of spectral data (1H and 13C NMR), the yields, HRMS,Mp and Rf of these precursors are presented in SupplementaryInformation.

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; Ameryckx, Alice; Thabault, Leopold; Pochet, Lionel; Leimanis, Serge; Poupaert, Jacques H.; Wouters, Johan; Joris, Bernard; Van Bambeke, Francoise; Frederick, Raphael; European Journal of Medicinal Chemistry; vol. 159; (2018); p. 324 – 338;,
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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. 17994-94-4, name is Methyl 7-aminoheptanoate hydrochloride, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: Methyl 7-aminoheptanoate hydrochloride

(b) Carbostyril-6-sulfonyl chloride (corresponding to 54) (138mg, 0.57mmol) and then subsequently Et3N (114mg, 3.24mmol) in CH2Cl2 (0.5ml) were added to a solution of 7-aminoheptanoic acid methyl ester hydrochloride (142mg, 0.73mmol) in CH2Cl2 (2ml) at room temperature. The reaction mixture was stirred for 16h at room temperature. H2O (10ml), AcOEt (10ml), and n-hexane (10ml) were then sequentially added to the mixture. The precipitate was gathered, washed with H2O, and dried to afford a pink solid (127mg, 0.35mmol, y. 61%). 1H NMR (300MHz/DMSO-d6) delta 1.15-1.20 (4H, m, CH2¡Á2), 1.29-1.44 (4H, m, CH2¡Á2), 2.22 (2H, t, J=7.2Hz, CH2), 2.72 (2H, q, J=6.0Hz, NCH2), 3.56 (3H, s, OCH3), 6.61 (1H, d, J=9.6Hz, CH=), 7.43 (1H, d, J=8.7Hz ArH), 7.53 (1H, t, J=5.9Hz, NH), 7.84 (1H, dd, J=8.7, 2.1Hz ArH), 8.07 (1H, d, J=9.6Hz, CH=), 8.13 (1H, d, J=2.1Hz, ArH), 12.01 (1H, br, NH).

According to the analysis of related databases, 17994-94-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Tashima, Toshihiko; Murata, Hiroaki; Kodama, Hidehiko; Bioorganic and Medicinal Chemistry; vol. 22; 14; (2014); p. 3720 – 3731;,
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Related Products of 609-08-5, 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 609-08-5 as follows.

Test tube equipped with a stir bar N- fluoro bis (methanesulfonyl) imide (38.2 mg, 0.2 mmol) and 1,2 g of dichloroethane (1.0 mL), at room temperature, and dissolved.Then, the same solution of 2-methylmalonic acid diethyl (17.4 mg, 0.1 mmol) and tetra -iso- propoxy orthotitanate (0.016 mL, 0.05 mmol) was added and subjected to room temperature, 12 hours .After completion of the reaction, addition of water, dichloromethane extraction (3 times), the combined organic layers washed with saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated to give a crude product. The resulting crude product was used hexafluorobenzene as internal standard in 19F-NMR measurement, 2-fluoro-2-methyl-diethyl malonate quantitatively the desired product was produced.Then purified by silica gel column chromatography (ethyl acetate / hexane = 10/90 vol / vol) ,to obtain purified 2-fluoro-2-methyl-malonic acid diethyl (7) as a colorless transparent liquid (18.7 mg, 0 .097mmol, 97% yield).

According to the analysis of related databases, 609-08-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NAGOYA INSTITUTE OF TECHNOLOGY; TOSOH F-TECH INCORPORATED; SHIBATA, NORIO; KAGAWA, TAKUMI; (11 pag.)JP2016/23178; (2016); A;,
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