Tag: M.W=200-300

Electric Literature of 50995-48-7,Some common heterocyclic compound, 50995-48-7, name is Methyl 2,5-dibromopentanoate, molecular formula is C6H10Br2O2, 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.

Reference Example 1 To a solution of 3.06 g of 2-amino-4,5-dimethylthiophenol in 50 ml of dimethylformamide was added 5.48 g of methyl 2,5-dibromovalerate at room temperature with stirring. The mixture was stirred for 14 hours, poured into water, and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4), and concentrated. The residue was washed with a mixture of ether and hexane to obtain 4.35 g (69.3percent) of 2-(3-bromopropyl)-6,7-dimethyl-2H-1,4-benzothiazin-3(4H)-one as crystals. Recrystallization from methanol gave prisms, m.p. 151¡ã-153¡ã C. IR(Nujol)cm-1: 3200, 1660. NMR delta(ppm)in CDCl3: 1.37-2.27(4H, m), 2.42(6H, s), 3.23-3.4(1H, m), 3.37(2H, t, J=6 Hz), 6.64(1H, s), 7.03(1H, s), 8.9(1H, broad). Elemental Analysis for C13 H16 BrNOS, Calcd.: C 49.69; H 5.13; N 4.46, Found: C 49.84; H 4.97; N 4.75.

The synthetic route of 50995-48-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Chemical Industries, Ltd.; US4640916; (1987); A;,
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Application of 1186-73-8, 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 1186-73-8 as follows.

Step 13; methyl 10-(((tert-butyldimethylsilyl)oxy)methyl)-l-(2,4-dimethoxybenzyl)-4- hydroxy-9-methyl-2-oxo-2,5,6,9-tetrahydro-lH-pyrido[2′,3′:4,5]oxepino[3,2- f] indole-3-carboxylate A solution of N-(8-((tert-butyldimethylsilyloxy)methyl)-9-methyl-3,4-dihydro-2H- oxepino[3,2-f]indol-5(9H)-ylidene)-l-(2,4-dimethoxyphenyl)methanamine (3.81 g crude) and trimethyl methanetricarboxylate (2.9 g, 15.0 mmol) in Ph20 (15 mL) was heated at 230 C for 15 min. The reaction mixture was cooled to room temperature and purified on silica gel using EtO Ac/Hex (0-60% gradient) to afford the product (2.0 g, 43%) as a yellow foam. XH NMR (500 MHz, DMSO-i) delta ppm 0.00 (d, J=0.95 Hz, 6 H) 0.77 – 0.83 (m, 9 H) 1.87 – 1.96 (m, 2 H) 2.88 – 2.96 (m, 1 H) 3.48 (s, 3 H) 3.64 (d, J=1.89 Hz, 6 H) 3.77 (s, 3 H) 4.21 (br. s., 2 H) 4.74 (s, 2 H) 4.98 – 5.07 (m, 1 H) 6.24 (s, 1 H) 6.37 (s, 2 H) 6.61 – 6.68 (m, 1 H) 7.21 (s, 1 H) 7.31 – 7.40 (m, 1 H) 13.28 – 13.36 (m, 1 H). LC-MS: 633.2 [M-H]”, RT 1.80 min.

According to the analysis of related databases, 1186-73-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PTC THERAPEUTICS, INC.; BRANSTROM, Arthur; JOSYULA, Vara Prasad, Venkata Nagendra; ARNOLD, Michael, Andrew; GERASYUTO, Aleksey, I.; KARP, Gary; WANG, Jiashi; WO2013/33228; (2013); A1;,
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These common heterocyclic compound, 619-42-1, name is Methyl 4-bromobenzoate, 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. Computed Properties of C8H7BrO2

To a stirred solution of methyl 4-bromobenzoic acid methyl ester (45 g, 209.0 mmol) in MeOH (500 mL), hydrazine hydrate (39.31 g, 627.0 mmol) was added at RT and heated to 65 C for 12h. After cooling the reaction mixture to RT, the solvent was removed under reduced pressure. The residue was slurred with diethyl ether (300 mL). The solid was filtered off and dried under suction to afford the title compound as an off white solid (40 g, 93% yield). NMR (400 MHz, DMSO-d6) delta 9.84 (s, 1H), 7.76- 7.73 (m, 2H), 7.66-7.64 (m, 2H), 4.49 (s, 2H) 1H NMR (DMSO-d6, 400MHz) delta 9.84 (s, 1H), 7.76-7.73 (m, 2H), 7.66-7.63 (m, 2H), 4.42 (b, 2H). LC/MS (Method A): 217.0(M+H)+. HPLC (Method F) Rt 2.02 min (Purity: 99.6%).

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

Reference:
Patent; ARES TRADING S.A.; QUATTROPANI, Anna; SWINNEN, Dominique; WO2013/182274; (2013); 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. 55666-43-8, name is tert-Butyl 3-bromopropanoate, A new synthetic method of this compound is introduced below., HPLC of Formula: C7H13BrO2

To a stirred mixture of 3-[(methylamino)methyl]benzonitrile (6.1 g, 41.7 mmol) and sodium bicarbonate (7.0 g, 83.4 mmol) in ACN (70 mL) was added dropwise tert-butyl 3-bromo- propanoate (7 mL, 41.7 mol). After being stirred at RT for 12 hours, the reaction mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was purified by chromatography (silica, pet ether/EtOAc) to afford the title compound as a pale yellow liquid. 1H NMR (DMSOd6, 400 MHz) delta 7.70 (s, 2H), 7.60 (m, 1 H), 7.51 (m, 1 H), 3.49 (s, 2H), 2.58 (m, 2H), 2.36 (m, 2H), 2.09 (s, 3H), 1.38 (s, 9H).

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; MERCK SERONO S.A.; QUATTROPANI, Anna; MONTAGNE, Cyril; SAUER, Wolfgang; CROSIGNANI, Stefano; BOMBRUN, Agnes; WO2010/112461; (2010); 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 23062-51-3 as follows. Quality Control of Methyl 4-bromobicyclo[2.2.2]octane-1-carboxylate

Intermediate A51E: Methyl 4-phenylbicyclo[2.2.2]octane-1-carboxylate To a suspension of aluminum trichloride (809 mg, 6.07 mmol) in benzene (4 mL, 1.214 mmol) at -10 C. was added a solution of Intermediate A51D (300 mg, 1.214 mmol) in benzene (2 mL) under nitrogen. The reaction mixture was gradually warmed up to RT and stirred overnight. It was carefully poured into ice water, extracted with EtOAc. The combined organic layer was washed with brine, dried over Na2SO4, and filtered. The filtrate was concentrated to afford Intermediate A51E (250 mg, 84%) as a tan solid, which was used for the next step without further purification. MS(ES): m/z=245 [M+H]+; 1H NMR (400 MHz, chloroform-d) delta ppm 7.42-7.29 (m, 4H), 7.29-7.16 (m, 1H), 3.77-3.65 (s, 3H), 2.07-1.80 (m, 1H).

According to the analysis of related databases, 23062-51-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Bristol-Myers Squibb Company; Velaparthi, Upender; Darne, Chetan Padmakar; Liu, Peiying; Wittman, Mark D.; Pearce, Bradley C.; Araujo, Erika M. V.; Dasgupta, Bireshwar; Nair, Jalathi Surendran; Janakiraman, Sakthi Kumaran; Rachamreddy, Chandrasekhar Reddy; Rao, Mettu Mallikarjuna; Karuppiah, Arul Mozhi Selvan Subbiah; Reddy, Bandreddy Subba; Nagalakshmi, Pulicharla; Bora, Rajesh Onkardas; Maheshwarappa, Shilpa Holehatti; Kumaravel, Selvakumar; Mullick, Dibakar; Sistla, Ramesh; (353 pag.)US9273058; (2016); B2;,
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Application of 541-16-2, 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. 541-16-2, name is Di-tert-Butyl malonate, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a cooled(0 C) solution of NaH (60% in mineral oil, 2.2 eq.) in DMF (1.0 M) was slowly added di-t-butylmalonate (1.1 eq.). After 15 min, 2-fluoronitrobenzene derivative (5.00 g) was added to the reactionmixture dropwise at 0 C. The resultant mixture was stirred at room temperature overnight and quenchedwith 0.1 N HCl aq. The resultant aqueous phase was extracted with EtOAc/n-hexane = 1/1. The combinedorganic phases were washed with brine. The resultant organic phase was dried over Na2SO4, filtered, andthe filtrate was concentrated in vacuo. The residue was purified by silica gel column chromatography(n-hexane/EtOAc = 100/0 – 30/70).

The chemical industry reduces the impact on the environment during synthesis Di-tert-Butyl malonate. I believe this compound will play a more active role in future production and life.

Reference:
Article; Yamai, Yu-Suke; Tanaka, Akio; Yajima, Tatsuo; Ishida, Kyoji; Natsutani, Itaru; Uesato, Shinichi; Nagaoka, Yasuo; Sumiyoshi, Takaaki; Heterocycles; vol. 97; 1; (2018); p. 192 – 210;,
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Related Products of 24807-40-7,Some common heterocyclic compound, 24807-40-7, name is Methyl 3-(4-(benzyloxy)phenyl)propanoate, molecular formula is C17H18O3, 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.

Methyl 2-((4-((phenylmethyl)oxy)phenyl)methyl)butanoate(32.1).; To a solution of lithium diisopropylamide (6.5 mL, 2.0 M in heptane/THF/ethylbenzene) in THF (25.0 mL) and l,3-dimethyl-3,4,5,6- tetrahydro-2(lH)-pyrimidinone (5.0 mL) was added methyl 3-(4- (benzyloxy)phenyl)propanoate 23.1 (3.00 g, 1 1 mmol) in THF (1OmL) and 1,3- dimethyl-3,4,5,6-tetrahydro-2(lH)-pyrimidinone (2.5 mL) at -780C. The resulting mixture was stirred at -780C for 30 minutes and then iodoethane (1.0 mL, 13 mmol) in THF (5.0 mL) was added. The reaction mixture was stirred at the same temperature for 20 minutes. The reaction was then stirred at room temperature for 16 hours. The reaction was quenched with water (30.0 mL), and the mixture was concentrated in vacuo. The residue was disolved in EtOAc (100 mL), washed with brine (2×25 mL), and dried with Na2SO4. The residue was purified by silica gel column (eluent with hexane/EtOAc; 85/15) to give the title compound 32.1. MS ESI (pos.) m/e: 299.0 (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 3-(4-(benzyloxy)phenyl)propanoate, its application will become more common.

Reference:
Patent; AMGEN INC.; WO2008/130514; (2008); A1;,
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935273-86-2, name is Benzyl 3,3-difluorocyclobutanecarboxylate, 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. name: Benzyl 3,3-difluorocyclobutanecarboxylate

Intermediate 296A: Benzyl 3,3-difluoro-1-methylcyclobutanecarboxylate To a solution of benzyl 3,3-difluorocyclobutanecarboxylate (2 g, 8.84 mmol) and MeI (2.202 mL, 35.4 mmol), in THF (15 mL) at -78 C. under a N2 atmosphere was added a solution of KHMDS (35.4 mL, 17.68 mmol, 0.5 M in toluene). The reaction mixture was then stirred at -78 C. for 6 h after which it was allowed to warm to RT and stir overnight. The reaction mass was then quenched with a saturated aq. solution of NH4Cl and extracted with diethyl ether (3*25 mL). The combined organic fractions were washed with water, dried over Na2SO4, filtered and concentrated under vacuum. The crude product was purified by silica gel chromatography (40 g REDISEP column, eluting with 20% EtOAc in hexanes). Fractions containing the product were combined and evaporated to afford the Intermediate 296A as a pale yellow liquid (1.2 g, 56.5%). 1H NMR (400 MHz, chloroform-d) delta ppm 7.50-7.23 (m, 5H), 5.17 (s, 2H), 3.22-2.97 (m, 2H), 2.60-2.28 (m, 2H), 1.51 (s, 3H).

The synthetic route of 935273-86-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bristol-Myers Squibb Company; Velaparthi, Upender; Darne, Chetan Padmakar; Liu, Peiying; Wittman, Mark D.; Pearce, Bradley C.; Araujo, Erika M. V.; Dasgupta, Bireshwar; Nair, Jalathi Surendran; Janakiraman, Sakthi Kumaran; Rachamreddy, Chandrasekhar Reddy; Rao, Mettu Mallikarjuna; Karuppiah, Arul Mozhi Selvan Subbiah; Reddy, Bandreddy Subba; Nagalakshmi, Pulicharla; Bora, Rajesh Onkardas; Maheshwarappa, Shilpa Holehatti; Kumaravel, Selvakumar; Mullick, Dibakar; Sistla, Ramesh; (353 pag.)US9273058; (2016); B2;,
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Adding a certain compound to certain chemical reactions, such as: 26218-04-2, name is 2-Ethylhexyl 4-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 26218-04-2, Product Details of 26218-04-2

77.5 g of a 20 wt % aqueous solution of Na2CO3, 190.0 g of xylene and 68.5 g of 2-ethylhexyl 4-aminobenzoate are loaded into a 1 litre flask equipped with mechanical stirrer, thermometer, reflux condenser and dropping funnel. Keeping the mixture stirred at 65 C., a solution of 47.1 g of 4-nitrobenzoyl chloride is added to 47.0 g of xylene. The resulting mixture is then heated to reflux for 1 h. The organic phase is cooled, and the reaction product precipitates. The product is recovered by filtration, washing with xylene and drying at 110 C. under vacuum, to obtain 83 g of yellow powder corresponding to 2-ethylhexyl 4-(4-nitrobenzamido) benzoate.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Ethylhexyl 4-aminobenzoate, and friends who are interested can also refer to it.

Reference:
Patent; 3V Sigma S.P.A.; Maestri, Francesco; Berte’, Ferruccio; (8 pag.)US2018/30001; (2018); A1;,
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Application of 773873-95-3,Some common heterocyclic compound, 773873-95-3, name is Methyl 2,2-difluorobenzo[d][1,3]dioxole-5-carboxylate, molecular formula is C9H6F2O4, 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.

[00193] (2,2-Difluorobenzo[d] [l,3]dioxol-5-yl)methanolMethod A: Methyl 2,2-difluorobenzo[Patent; VERTEX PHARMACEUTICALS INCORPORATED; WO2007/21982; (2007); A2;,
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