Tag: M.W=200-300

Application of 1731-79-9, These common heterocyclic compound, 1731-79-9, name is Dimethyl dodecanedioate, 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 cooled (0 C) solution of LiAlH4 (1.73 g, 45.6 mmol) in THF (280 mL) was added a solution ofdimethyl dodecanedioate (4.35 g, 15.2 mmol) in THF (20 mL) dropwise, and the resulting solution wasstirred at 0 C for 3 h. Then, the reaction mixture was quenched with MeOH and 1 M HCl. The organic layer wasseparated and the aqueous layer was extracted with diethyl ether three times. The combined organic layer was washedwith water and brine, and dried over sodium sulfate. After evaporation of the solvent, the product was obtained(3.22 g, 92%) in high purity, which was then used in the next step without further purification.1H-NMR (500 MHz, CDCl3): delta3.64 (t, J =7.5 Hz, 4H, 1-H, 14-H), 1.57 (m, 4H, 2-H, 13-H), 1.35-1.26(20H, 3-H to 12-H)13C-NMR (125 MHz, CDCl3): delta63.1 (C1, C14), 32.8 (C2, C13), 29.6, 29.6, 29.5, 29.4 (C4 to C11), 25.7(C3, C12)HR-MS (ESI-TOF): m/z calcd for C14H30O2Na [M+Na]+ 253.2138, found 253.2137IR (film): 3409, 3347, 2923, 2854 cm

The synthetic route of 1731-79-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Tonoi, Takayuki; Kawahara, Ryo; Yoshinaga, Yutaka; Inohana, Takehiko; Fujimori, Keiko; Shiina, Isamu; Tetrahedron Letters; vol. 56; 11; (2015); p. 1356 – 1359;,
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Related Products of 252881-74-6, 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. 252881-74-6, name is tert-Butyl 3-(2-(2-(2-aminoethoxy)ethoxy)ethoxy)propanoate, This compound has unique chemical properties. The synthetic route is as follows.

Step 4: 3-{2-[2-(2-{4-[4-(3,5-Dioxo-hexyl)-phenylcarbamoyl]-butyrylamino}-ethoxy)-ethoxy]-ethoxy}-propionic acid tert-butyl ester A solution of 4-[4-(3,5-dioxo-hexyl)-phenylcarbamoyl]-butyric acid 2,5-dioxo-pyrrolidin-1-yl ester (1.5 g, 3.6 mmol), 3-{2-[2-(2-amino-ethoxy)-ethoxy]-ethoxy}-propionic acid tert-butyl ester (1.0 g, 3.6 mmol) and DIEA (1.3 muL, 7.2 mmol) in CH2Cl2 (10 mL) was stirred at room temperature overnight. The solvent was removed in vacuo and the residual oil purified using column chromatography EtOAc/MeOH (95:5) to give the title compound as a transparent oil, (M+1)=579.

The chemical industry reduces the impact on the environment during synthesis tert-Butyl 3-(2-(2-(2-aminoethoxy)ethoxy)ethoxy)propanoate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; BRADSHAW, Curt W.; Sakamuri, Sukumar; Fu, Yanwen; Oates, Bryan; Desharnais, Joel; Tumelty, David; US2009/98130; (2009); A1;,
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Adding a certain compound to certain chemical reactions, such as: 15964-79-1, name is Methyl 2-(3,4-dimethoxyphenyl)acetate, 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 15964-79-1, COA of Formula: C11H14O4

Manufacturing Example 13: Preparation of 2-(3,4-Dimethoxyphenyl) acetaldehyde (52) Anhydrous diethyl ether solution containing methyl 3′,4′-dimethoxyphenyl acetate (1.94 g, 9.24 mmol) was stirred, during which DIBAL-H (11.1 mL, 1 M in THF solution) was added thereto drop by drop with maintaining the temperature at -78C. The mixture was stirred at the same temperature for 1 hour. Rochelle aqueous solution was carefully added thereto for 15 minutes. The mixture of the two phases was stirred vigorously at 0 C for 1 hour, which was added to water. The water layer was extracted with EtOAc (*2) and the organic layer was dried over MgSO4, filtered and concentrated under reduced pressure. Then, the obtained residue was purified by flash column chromatography (EtOAc:n-hexane=1:2) to give the compound 52 of Manufacturing Example 13 (yield: 68%, 1.13 g). 1H NMR (CDCl3, 300 MHz) delta 9.66 (t, 1H, J = 2.5 Hz), 6.80 (d, 1H, J = 8.0 Hz), 6.68 (m, 1H), 6.64 (d,

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 2-(3,4-dimethoxyphenyl)acetate, and friends who are interested can also refer to it.

Reference:
Patent; SNU R&DB Foundation; SUH, Young-Ger; CHANG, Dong-Jo; AN, Hongchan; KIM, Kyu-Won; KIM, Young-Myeong; LEE, Ho-Young; EP2871187; (2015); A1;,
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Adding a certain compound to certain chemical reactions, such as: 110661-91-1, name is tert-Butyl 4-bromobutanoate, 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 110661-91-1, Application In Synthesis of tert-Butyl 4-bromobutanoate

[000730] To a solution of Example 1.2.7 (0.103 g) and tert-butyl 4-bromobutanoate (0.032 g) in dichloromethane (0.5 inL) was added N,N-diisopropylethylamine (0.034 mL) at 50 C in a sealed amber vial overnight. The reaction was concentrated, dissolved in dimethyl sulfoxide/methanol (1 : 1, 2 mL) and purified by reverse phase HPLC using a Gilson system, eluting with 5-75% acetonitrile in water containing 0.1% v/v trifluoroacetic acid. The desired fractions were combined and freeze-dried to provide the title compound. MS (ESI) m/e 944.6 (M+l).

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

Reference:
Patent; ABBVIE INC.; TAO, Zhi-Fu; DOHERTY, George; WANG, Xilu; SULLIVAN, Gerard M.; SONG, Xiaohong; KUNZER, Aaron R.; WENDT, Michael D.; MARIN, Violeta L.; FREY, Robin R.; CULLEN, Steve C.; WELCH, Dennie S.; SHEN, Xiaoqiang; BENNETT, Nathan B.; HAIGHT, Anthony R.; ACKLER, Scott L.; BOGHAERT, Erwin R.; SOUERS, Andrew J.; JUDD, Andrew S.; (623 pag.)WO2016/94509; (2016); 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. 1014645-87-4, name is Methyl 4-(1-aminocyclopropyl)benzoate hydrochloride, This compound has unique chemical properties. The synthetic route is as follows., Formula: C11H14ClNO2

Description 169: methyl 4-(1-(5-chloro-2-(3-((2,4- difluorophenyl)amino)azetidin-1-yl)nicotinamido)cyclopropyl)benzoate (D169)A mixture of 5-chloro-2-(3-((2,4-difluorophenyl)amino)azetidin-1 -yl)nicotinic acid (D1 18) (40 mg, 0.1 18 mmol), 1 -Hydroxybenzotriazole hydrate (18 mg, 0.1 18 mmol) and 1 -Ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (34 mg, 0.177 mmol) in dimethylformamide (5ml) was stirred 10 min at room temperature. A solution of methyl 4-(1 -aminocyclopropyl)benzoate hydrochloride (D7) (32.2 mg, 0.141 mmol) and triethylamine (0.02ml, 0.141 mmol) in dry dimethylformamide (2ml) was added and the mixture was stirred 24h at room temperature. After solvent evaporation, water (10ml) was added and the formed precipitate was filtered off and purified by Biotage SNAP-Si (1 Og) cartridge eluting with a mixture dichloromethane/methanol from 100/0 to 80/20. Collected fractions, after solvent evaporation afforded the title compound (D169) (105 mg).MS: (ES/+) m/z: 513.2 [MH+] C26H23CIF2N403 requires 512.141 H NMR (400MHz ,DMSO-d6) delta = 9.23 (s, 1 H), 8.21 (d, J = 2.4 Hz, 1 H), 7.91 – 7.80 (m, J = 8.3 Hz, 2 H), 7.74 (d, J = 2.4 Hz, 1 H), 7.40 – 7.29 (m, J = 8.3 Hz, 2 H), 7.18 – 7.06 (m, 1 H), 6.85 (t, J = 8.6 Hz, 1 H), 6.48 (d, J = 5.4 Hz, 1 H), 6.03 (br. s., 1 H), 4.22 (d, J = 3.9 Hz, 3 H), 3.86 (s, 3 H), 3.76 (d, J = 4.9 Hz, 2 H), 1 .34 (d, J = 9.3 Hz, 4 H)

According to the analysis of related databases, 1014645-87-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ROTTAPHARM S.P.A.; BORRIELLO, Manuela; ROVATI, Lucio; STASI, Luigi Piero; BUZZI, Benedetta; COLACE, Fabrizio; WO2012/76063; (2012); 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. 2876-78-0, name is Methyl 1-Naphthaleneacetate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. name: Methyl 1-Naphthaleneacetate

Methylmagnesium bromide (3 M in ether, 10 mL, 30 mmol) was added dropwise to a solution of methyl naphthalene-1-acetate (2.0 g, 10 mmol) in tetrahydrofuran (20 mL) at 0 C. under a nitrogen atmosphere. After stirring at room temperature overnight, the reaction mixtures was quenched by the addition of water. The organic fraction was washed with brine, dried over sodium sulfate and concentrated under vacuum to give crude 2-methyl-1-(naphthalene-1-yl)propan-2-ol (2.0 g) as a yellow oil, which was used directly in the next step.The crude alcohol (2.0 g, 10 mmol) was dissolved in acetonitrile (10 mL) and concentrated sulfuric acid (4.9 g, 50 mmol) was added dropwise at 0 C. After stirring at room temperature for 2 hours, the reaction mixture was diluted with water and extracted with dichloromethane. The combined organic fractions were dried over sodium sulfate and evaporated. The residue was purified by silical gel column chromatography (petroleum ether/ethyl acetate) to give N-(2-methyl-1-(naphthalene-1-yl)propan-2-yl)acetamide (0.90 g, 37% yield) as a yellow solid.Concentrated hydrochloric acid (10 mL) was added to a solution of the intermediate acetamide (0.20 g, 0.83 mmol) in dioxane (2 mL) and the resulting mixture was refluxed for 3 days. After cooling to room temperature, the reaction mixture was basified to pH 9 by the addition of solid sodium bicarbonate. The mixture was extracted with ethyl acetate and the combined organic fractions were dried over sodium sulfate and concentrated to give crude 2-methyl-1-(naphthalene-1-yl)propan-2-amine (0.15 g, 23% yield) as a yellow oil, which was used without further purification.The crude amine (153 mg, 0.25 mmol), compound 1 (48 mg, 0.13 mmol) and potassium carbonate (36 mg, 0.25 mmol) were taken up in dioxane (2 mL) and heated to reflux overnight. The reaction mixture was concentrated under vacuum and the residue was purified by prep-HPLC to give compound A27 (16 mg, 23% yield) as a white solid: >99.5% purity (HPLC); MS m/z: 530.3 (M+1); 1H NMR (CDCl3, 500 MHz) delta 8.29 (d, J=8.0 Hz, 1H), 8.15 (d, J=7.0 Hz, 1H), 7.88 (d, J=6.5 Hz, 2H), 7.77 (d, J=8.0 Hz, 1H), 7.56 (t, JHF=54.0 Hz, 1H), 7.48 (m, 2H), 7.39 (m, 3H), 7.27 (d, J=7.0 Hz, 1H), 5.29 (s, 1H), 4.02-3.73 (m, 8H), 3.66 (s, 2H), 1.54 (s, 6H) ppm

The synthetic route of 2876-78-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Pathway Therapeutics Inc.; US2012/252802; (2012); 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. 6942-37-6, name is Methyl 5-amino-2-bromobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. category: esters-buliding-blocks

Step B. Preparation of methyl 2-bromo-5-(dimethylamino)benzoateTo a stirred solution of 5-amino-2-bromo-benzoic acid methyl ester (3.30 g, 14.35 mmol) in CH3OH (45 mL) containing CH2O (3.6 mL, 45.0 mmol) at room temperature was added a solution of NaBH3CN (945 mg, 14.35 mmol) and ZnCI2 (990 mg, 7.2 mmol) in CH3OH (45 mL). The reaction mixture was stirred at room temperature overnight, then concentrated. The residue was taken up in 0.1 N NaOH solution, extracted with EtOAc several times. The combined extracts were washed with H2O, brine, dried over dried Na2SO4, then filtered and concentrated. The residue was separated by silica gel column (hexane/EtOAc = 3 : 1) to give 2.991 g (92%) of methyl 2-bromo-5-(dimethylamino)benzoate as a yellow oil based on the partial recovery of (412 mg). methyl 2-bromo-5-(dimethylamino)benzoate, MS: m/z 259 (M + H)

The synthetic route of 6942-37-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; WYETH; WO2009/120826; (2009); A1;,
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6091-64-1, name is Ethyl 2-bromobenzoate, 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. Computed Properties of C9H9BrO2

General procedure: The following experimental procedure for the partial alkynylation of ethyl benzoate to 1,3-diphenylprop-2-yn-1-one is representative. A dry and argon-flushed flask, equipped with a magnetic stirring bar and a septum, was charged with phenyl acetylene (0.45 mL, 4.1 mmol) and THF (10 mL). After cooling to 0 C, n-BuLi (1.6 mL, 2.5 M in hexane, 4.0 mmol) was added dropwise and stirred for 1 h at room temperature. To the reaction mixture was slowly added morpholine (0.08 mL, 1.0 mmol) and stirred for 30 min at 0 C. Then, ethyl benzoate (0.14 mL, 1.0 mmol) was added and the mixture was stirred for 6 h again. The reaction was stopped by aqueous NH4Cl (aq) (10 mL) and extracted with diethyl ether (2 * 10 mL). The combined organic layers were dried over MgSO4, filtered, and concentrated under reduced pressure. Purification of the residue by column chromatography on silica gel yielded 1,3-diphenylprop-2-yn-1-one (175 mg, 85%). All products in Table 2 were confirmed by comparison with NMR data reported of authentic sample.7

The synthetic route of 6091-64-1 has been constantly updated, and we look forward to future research findings.

Reference:
Note; Shin, Won Kyu; Kim, Yu Ri; Im, So Hee; Jaladi, Ashok Kumar; Gundeti, Shankaraiah; An, Duk Keun; Bulletin of the Korean Chemical Society; vol. 39; 5; (2018); p. 683 – 686;,
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Some common heterocyclic compound, 14062-30-7, name is Ethyl 2-(3-bromophenyl)acetate, molecular formula is C10H11BrO2, 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. HPLC of Formula: C10H11BrO2

(3-Cyano-phenyl)-acetic acid ethyl ester A mixture of (3-bromo-phenyl)-acetic acid ethyl ester (9.15 g, 37.6 mmol), copper cyanide (5.06 g, 56.5 mmol), and 1-methyl-2-pyrrolidinone (80 mL) was placed into an oil bath heated at 120 C. behind a protective shield. The reaction was heated to 200 C. for 1 h and additional copper cyanide (spatula tip) was added. After heating for an additional 0.5 h, the reaction was cooled to room temperature. The reaction was diluted with EtOAc and the organic solution was washed with water/ammonium hydroxide solution (2:1 v/v) until the aqueous solution was no longer blue. The organic solution was washed with brine, dried (MgSO4), filtered, and concentrated. Flash chromatography (9:1 hexanes:EtOAc) provided (3-cyano-phenyl)-acetic acid ethyl ester (6.31 g) as a clear oil which solidified on standing. 1H NMR (400 MHz, CDCl3) delta7.57-7.50 (m, 3H), 7.42 (m, 1H), 4.15 (q, 2H), 3.63 (s, 2H), 1.24 (t, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 14062-30-7, its application will become more common.

Reference:
Patent; Pfizer Inc.; US6344485; (2002); B1;,
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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. 185312-82-7, name is Methyl 4-bromo-2-chlorobenzoate, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C8H6BrClO2

Preparation Example 10-1 To a solution of methyl 4-bromo-2-chlorobenzoate (1.25 g) in N,N-dimethylformamide (10 ml) was added sodium thiomethoxide (459 mg) under ice-cooling and the mixture was stirred for 2 hr. To the reaction mixture was added 1N hydrochloric acid and the resulting product was extracted 3 times with diethyl ether. The organic layers were combined, washed successively with water and saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated and the residue was applied to silica gel column chromatography (hexane/ethyl acetate=10/1) to give methyl 2-chloro-4-(methylthio)benzoate (835 mg) as a colorless oil. 1H-NMR(CDCl3): 2.49(3H, s), 3.90(3H, s), 7.11(1H, d, J=8Hz), 7.23(1H, s), 7.78(1H, d, J=8Hz).

According to the analysis of related databases, 185312-82-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; FUJISAWA PHARMACEUTICAL CO., LTD.; EP1142879; (2001); A1;,
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