Tag: M.W=100-200

Synthetic Route of 61367-07-5, These common heterocyclic compound, 61367-07-5, name is Methyl trans-4-aminocyclohexanecarboxylate hydrochloride, 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.

Example 19(1r,4R)-4-(2-phenyl-1H-indole-6-sulfonamido)-N-((R)-1-(pyridin-2-yl)ethyl)cyclohexanecarboxamide Step 1. Preparation of (1r,4r)-methyl 4-(4-chloro-3-nitrophenylsulfonamido)cyclo hexanecarboxylate; (1r,4r)-methyl 4-aminocyclohexanecarboxylate HCl salt (7.75 g, 40 mmol) was suspended in a mixture of DCM (50 mL) and then treated with triethylamine (22.31 mL, 160 mmol), followed by 4-chloro-3-nitrobenzene-1-sulfonyl chloride (11.27 g, 44 mmol). The reaction mixture was stirred at rt for 2 h and then concentrated under reduced pressure. The residue was taken up in ethyl acetate (100 mL) and washed with 1N aq. HCl (3¡Á100 mL), brine (100 mL) and dried over sodium sulfate. Filtration and concentration of the organic solution gave product (14.1 g) as a yellow solid (MS: (M+H)+=377.3).

The synthetic route of 61367-07-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; US2012/28969; (2012); A1;,
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Reference of 6933-47-7, 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. 6933-47-7 name is Methyl 4-amino-2-methylbenzoate, 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: Step (viii): Methyl 4-(3-chloro-4-ethoxy-5-isopropoxybenzamido)-2-methylbenzoate. A suspension of 217 3-chloro-4-ethoxy 5-isopropoxybenzoic acid (48: R2=iPr, R3=Et) (2.82g, 10.9mmol) and 145 methyl 4-amino-2-methylbenzoate (38: R1=Me) (2.16g, 13.1mmol) in 45 ethyl acetate (33mL) was treated with 46 triethylamine (4.56mL, 32.7mmol) followed by 44 T3P (50wt% in ethyl acetate) (17.34mL, 27.3mmol) and the mixture was heated at 60C for 4h and allowed to cool to room temperature for 16h. The reaction mixture was stirred vigorously with an aqueous solution of 218 sodium hydrogencarbonate (50mL) for 10min and separated. The aqueous layer was extracted with dichloromethane (3¡Á100mL) and the combined organic phases were dried (magnesium sulfate), filtered concentrated in vacuo and the residue purified by silica gel chromatography (40g, 0:50:50 to 20:40:40 ethyl acetate:120 dichloromethane:isohexane) to produce 219 methyl 4-(3-chloro-4-ethoxy-5-isopropoxybenzamido)-2-methylbenzoate as a beige solid (3.24g, 70% yield).

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

Reference:
Article; Clarke, Earl; Jarvis, Christopher I.; Goncalves, Maria B.; Kalindjian, S. Barret; Adams, David R.; Brown, Jane T.; Shiers, Jason J.; Taddei, David M.A.; Ravier, Elodie; Barlow, Stephanie; Miller, Iain; Smith, Vanessa; Borthwick, Alan D.; Corcoran, Jonathan P.T.; Bioorganic and Medicinal Chemistry; vol. 26; 4; (2018); p. 798 – 814;,
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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. 369-25-5, name is Methyl 3,4-difluorobenzoate, This compound has unique chemical properties. The synthetic route is as follows., Safety of Methyl 3,4-difluorobenzoate

General procedure: 1,2-Dihydro-indazol-3-one (500 mg; 3.73 mmol; 1.00 eq.), cesium carbonate (3.64 g; 11.2 mmol; 3.00 eq.) and methyl 3,4-difluorobenzoate (1.28 g; 7.46 mmol; 2.00 eq.) were stirred at 120 C in a round bottom flask for 3 hours. 1,2-Dichloro-3-nitrobenzene (1.43 g; 7.46 mmol; 2.00 eq.) was added and the reaction mixture was heated at 120 C for an additional 2 hours. The reaction mixture was cooled and diluted in ethyl acetate (50 mL). The organic layer was washed with a saturated solution of NH4Cl (20 mL), a saturated solution of Na2CO3(20 mL) and brine (20 mL). The organic layer was dried over MgSO4, filtered and concentrated. The residue was purified using silica gel chromatography using heptane/ethyl acetate (5/5) as eluent. Methyl 4-(3-(2-chloro-6-nitrophenoxy)-1H-indazol-1-yl)-3-fluorobenzoate was isolated as a pale orange solid (1.00 g; 60.7%).1H NMR (DMSO-d6) delta: 3.90 (s, 3H), 7.43 – 7.36 (m, 1H), 7.50 (dd,J =8.7, 3.9 Hz, 1H), 7.68 – 7.57 (m, 3H), 7.99 – 7.90 (m, 3H), 8.11 (dd,J =8.2, 1.5 Hz, 1H), 8.20 (dd,J =8.3, 1.6 Hz, 1H)MS-ESIm/z442 [MH+].

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 369-25-5.

Reference:
Article; Ouvry, Gilles; Bouix-Peter, Claire; Ciesielski, Fabrice; Chantalat, Laurent; Christin, Olivier; Comino, Catherine; Duvert, Denis; Feret, Christophe; Harris, Craig S.; Lamy, Laurent; Luzy, Anne-Pascale; Musicki, Branislav; Orfila, Danielle; Pascau, Jonathan; Parnet, Veronique; Perrin, Agnes; Pierre, Romain; Polge, Gaelle; Raffin, Catherine; Rival, Yves; Taquet, Nathalie; Thoreau, Etienne; Hennequin, Laurent F.; Bioorganic and Medicinal Chemistry Letters; vol. 26; 23; (2016); p. 5802 – 5808;,
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Adding a certain compound to certain chemical reactions, such as: 106614-28-2, name is Methyl 2,4-difluorobenzoate, 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 106614-28-2, SDS of cas: 106614-28-2

Intermediate 28: Methyl 2-fluoro-4-(piperazin-1-yl)-benzoate Dimethyl sulfoxide (1.0 ml) was added to 544 mg of piperazine to prepare a suspension, and 368 mg of methyl 2,4-difluorobenzoate was added to the suspension. The mixture was stirred at 80 C. for 1 hr and was then cooled to room temperature. The reaction solution was concentrated under the reduced pressure. The residue was purified by column chromatography on silica gel (development system: methylene chloride-methanol-concentrated aqueous ammonia=900:100:1) to prepare 274 mg of the title compound. Physicochemical Properties of Intermediate 28

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Meiji Seika Kaisha, Ltd.; US6451800; (2002); B1;,
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Reference of 3618-04-0,Some common heterocyclic compound, 3618-04-0, name is trans-Ethyl 4-hydroxycyclohexanecarboxylate, molecular formula is C9H16O3, 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(chloro)diphenylsilane (18 ml, 68 mmol, CAS No 58479-61-1 ) was added drop wise to a mixture of ethyl 4-hydroxycyclohexanecarboxylate (9.4 ml, 57 mmol, CAS No 17159-80-7), 1H-imidazole (9.68 g, 142 mmol, CAS No 16681-56-4) and N,N-dimethylpyridin-4-amine (348 mg, 2.85 mmol, CAS No 1 122-58-3) in dimethylformamid (81 ml), and the mixture was stirred at room temperature for 24 h. For work-up, the mixture was poured into water, extracted with ethyl acetate (3x) and the combined organic phases were washed until pH=7 as reached. The organic phase was dried over sodium sulfate and was concentrated under reduced pressure. The residue was purified by flash chromatography (340 g Snap cartridge, hexane/ethyl acetate gradient, 5percent -> 30percent ethyl acetate) to give the title compound (21 g)

The synthetic route of 3618-04-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; BUCHGRABER, Philipp; EIS, Knut; WAGNER, Sarah; SUeLZLE, Detlev; VON NUSSBAUM, Franz; BENDER, Eckhard; LI, Volkhart, Min-Jian; LIU, Ningshu; SIEGEL, Franziska; LIENAU, Philipp; (248 pag.)WO2018/78005; (2018); A1;,
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96999-01-8, name is Methyl 1-bromocyclopropanecarboxylate, 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 C5H7BrO2

A mixture of 12j (2.40 g, 10 mmol), 3a-3b (15 mmol) andCs2CO3 (9.77 g, 30 mmol) in DMF (50 mL) was stirred at 90 C(for 3a) or 120 C (for 3b) in N2 atmosphere until the completion of reaction as indicated by TLC (typically within 12 h). Oncooling to room temperature, the reaction mixture was pouredinto ice-water (200 mL), and the mixture thus obtained wasextracted with CH2Cl2 (3 ¡Á 100 mL). The combined extractswere washed with 5% brine (5 ¡Á 100 mL), dried over anhydrous Na2SO4 and evaporated on a rotary evaporator to aord aresidue, which was purifed by column chromatography to yield21a-21b after trituration with EtOAc/n-hexane.6-Bromo-4-methylthioquinoline (21a). 1.07 g (42%). Whitesolid, m.p. 88-90 C. 1H NMR, delta 8.75 (d, J = 4.8 Hz, 1H),8.14 (d, J = 1.6 Hz, 1H), 7.94 (d, J = 8.8 Hz, 1H), 7.90 (dd,J = 2.0 Hz and 9.2 Hz, 1H), 7.40 (d, J = 4.8 Hz, 1H), 2.66(s, 3H). 13C NMR, delta 149.97, 146.97, 145.21, 132.71, 131.85,126.63, 124.88, 119.56, 116.27, 13.37. ESI-HR-MS, calcd. forC10H9BrNS ([M(79Br)+H]+) 253.9639, found 253.9641; calcd.for C10H9BrNS ([M(81Br)+H]+) 255.9619, found 255.9628.

The synthetic route of 96999-01-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhang, Xiansheng; Wu, Jingwei; Liu, Yuqiang; Xie, Yafei; Liu, Changying; Wang, Jianwu; Zhao, Guilong; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 192; 7; (2017); p. 799 – 811;,
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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. 178747-79-0, name is Methyl 2-fluoro-6-methoxybenzoate, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C9H9FO3

Reference Example 45 2-(2-Fluoro-6-methoxyphenyl)-2-propanol To a solution of methyl 2-fluoro-6-methoxybenzoate (0.92 g) in tetrahydrofuran (12.5 mL) was added methylmagnesium iodide (3.0 mol/L diethyl ether solution, 5 mL) under ice-cooling, and the mixture was stirred at room temperature overnight. To the reaction mixture was added a saturated aqueous ammonium chloride solution, and the resulting mixture was extracted with ethyl acetate. The extract was washed with water and brine, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: n-hexane – n-hexane/ethyl acetate = 1/1) to give the title compound (0.8 g).

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 178747-79-0.

Reference:
Patent; Kissei Pharmaceutical Co., Ltd.; EP2143724; (2010); A1;,
Ester – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 443-26-5, name is Ethyl 2-fluorobenzoate, 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 443-26-5, Recommanded Product: Ethyl 2-fluorobenzoate

General procedure: A mixture of substituted ethyl benzoate 2 (10 mmol) and hydrazinehydrate (20 mmol) in ethanol was stirred at room temperaturefor 3 h and then filtered. The crude product recrystallizedfrom absolute alcohol to give 3a-l, which were used directly forthe next step. Under this same condition, the intermediate compounds 8a-d were also prepared.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Article; He, Haifeng; Wang, Wei; Zhou, Yuan; Xia, Qin; Ren, Yanliang; Feng, Jiangtao; Peng, Hao; He, Hongwu; Feng, Lingling; Bioorganic and Medicinal Chemistry; vol. 24; 8; (2016); p. 1879 – 1888;,
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Electric Literature of 18595-12-5, A common heterocyclic compound, 18595-12-5, name is Methyl 5-amino-2-methylbenzoate, molecular formula is C9H11NO2, 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.

REFERENTIAL EXAMPLE 43 Production of 6-methyl-3-(1-pyrrolyl)benzyl alcohol 158 mg of methyl 3-amino-6-methylbenzoate was dissolved in 3 ml of acetic acid, and 139 mg of 2,5-dimethoxytetrahydrofuran was added. The mixture was heated under reflux for 1 hour. The reaction mixture was evaporated to dryness under reduced pressure. The residue was purified by silica gel column chromatography Wakogel C-200, 10 g; eluding solvent: hexane/ethyl acetate=10/1) to give 185 mg (yield 87%) of methyl 3-(1-pyrrolyl)-6-methylbenzoate, m.p. 56-57 C.

The synthetic route of 18595-12-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Banyu Pharmaceutical Co., Ltd.; US5234946; (1993); A;,
Ester – Wikipedia,
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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. 1678-68-8, name is trans-Ethyl 4-aminocyclohexanecarboxylate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of trans-Ethyl 4-aminocyclohexanecarboxylate

Ethyl trans-4-aminocyclohexanecarboxylate (J. Med. Chem., 1971, 14, 600-614) (29.5 g, 143 mmol) was dissolved in 1,4-dioxane (290 ml) and water (290 ml), triethylamine (30.0 ml, 215 mmol) and 1-[2-(trimethylsilyl)ethoxycarbonyloxy]pyrrolidine-2,5-dione (40.8 g, 157 mmol) were added under ice cooling and the resulting mixture was stirred at room temperature for 2 days. The reaction mixture was concentrated and then the residue was diluted with ethyl acetate and washed with 10% aqueous citric acid solution, saturated sodium bicarbonate solution, and brine in that order. The organic layer was dried over anhydrous sodium sulfate and the solvent was concentrated under reduced pressure to give 44.3 g (98%) of the title compound as colorless needle-like crystals.1H-NMR (500 MHz, CDCl3) delta: 0.03 (9H, s), 0.92-1.01 (2H, m), 1.08-1.18 (2H, m), 1.25 (3H, t, J=7.2 Hz), 1.48-1.59 (2H, m), 1.97-2.11 (4H, m), 2.21 (1H, tt, J=12.3, 3.7 Hz), 3.38-3.54 (1H, m), 4.07-4.19 (4H, m), 4.38-4.49 (1H, m).

The synthetic route of 1678-68-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sugimoto, Yuuichi; Uoto, Kouichi; Wakabayashi, Takanori; Miyazaki, Masaki; Setoguchi, Masaki; Taniguchi, Toru; Yoshida, Keisuke; Yamaguchi, Akitake; Yoshida, Shoko; US2012/264738; (2012); A1;,
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