Tag: M.W=200-300

Electric Literature of 1014645-87-4,Some common heterocyclic compound, 1014645-87-4, name is Methyl 4-(1-aminocyclopropyl)benzoate hydrochloride, molecular formula is C11H14ClNO2, 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: To a solution of selected acid (1 eq) in DMF, HCTU (1.1 eq) and DIPEA (2.5 eq) were added in sequence and the resulting mixture was stirred 30 min before adding the selected amine (1.1 eq). The mixture was left stirring at RT for 1-18 hrs then the reaction mixture was partitioned between EtOAc and H2O and the organic phase was separated. The aqueous phase was washed with EtOAc. All the collected organic phases were washed with NaCl sat. sol., dried over Na2SO4 and the solvent was removed under reduced pressure. The residue was purified on SPE-Si cartridge or Biotage SNAP-Si column eluting with a mixture of DCM/EtOAc from 100:0 to 95:5 affording the title amide compound. The title compound (D58) (250 mg) was prepared according to the general procedure for amides preparation (Method C) starting from 1-(tert-butoxycarbonyl)-4,4-dimethylpiperidine-2-carboxylic acid (320 mg; described in J. Med. Chem. 1997, 40, 2491-2501) and methyl 4-(1-aminocyclopropyl)benzoate hydrochloride (312 mg). Reaction time: 18 hrsMS: (ES/+) m/z: 431.4 [MH+] C24H34N2O5 requires 430.251H NMR (400 MHz, CHCl3-d) delta (ppm): 7.96 (d, J=8.2 Hz, 2H), 7.32-7.29 (m, 2H), 6.82-6.59 (m, 1H), 4.65 (d, J=4.4 Hz, 1H), 4.02 (br. s., 1H), 3.92 (s, 3H), 3.00 (d, J=10.6 Hz, 1H), 2.18 (d, J=12.9 Hz, 1H), 1.50 (s, 9H), 1.43-1.29 (m, 7H), 0.96 (s, 3H), 0.84 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 4-(1-aminocyclopropyl)benzoate hydrochloride, its application will become more common.

Reference:
Patent; Borriello, Manuela; Pucci, Sabrina; Stasi, Luigi Piero; Rovati, Lucio; US2015/87626; (2015); A1;,
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Reference of 1186-73-8,Some common heterocyclic compound, 1186-73-8, name is Trimethyl methanetricarboxylate, molecular formula is C8H12O6, 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.

Step 5; methyl 9-(((tert-butyldimethylsilyl)oxy)methyl)-l-(2,4-dimethoxybenzyl)-4- hydroxy-8-methyl-2-oxo-2,5,6,8-tetrahydro-lH-indolo[6,5-h]quinoline-3- carboxylate The N-(2-(((tert-butyldimethylsilyl)oxy)methyl)- 1 -methyl-7,8-dihydro- 1H- benzo[f]indol-5(6H)-ylidene)-l-(2,4-dimethoxyphenyl)methanamine (1.40 g, 2.84 mmol) and trimethyl methanetricarboxylate (0.95 g, 5.00 mmol) were mixed together in PI12O (7.0 mL). With stirring, the mixture was placed onto a pre-heated heat block at 230 C and heated for 10 min after the initial bubbling of MeOH was observed (occurs at -160 C internal reaction temperature) under a blanket of Argon. The reaction mixture was cooled to room temperature, then purified by column chromatography (hexanes followed by EtOAc/hexanes 25-60% gradient) to yield the product as a yellow foam (1.158 g, 63% 2 steps). XH NMR (500 MHz, CHCl3-i/) delta ppm 0.06 (s, 6 H) 0.90 (s, 9 H) 2.58 – 2.72 (m, 2 H) 2.89 (t, J=6.6 Hz, 2 H) 3.62 (s, 3 H) 3.78 (s, 3 H) 3.80 (s, 3 H) 3.97 (s, 3 H) 4.77 (s, 2 H) 5.37 (s, 2 H) 6.19 (s, 1 H) 6.42 (d, J=2.4 Hz, 1 H) 6.46 (dd, J=8.4, 2.4 Hz, 1 H) 7.14 (d, J=8.4 Hz, 1 H) 7.18 (s, 1 H) 7.63 (s, 1 H) 13.60 (s, 1 H). LC-MS 619.6 [M+H]+, RT 1.76 min.

The synthetic route of 1186-73-8 has been constantly updated, and we look forward to future research findings.

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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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. 148547-19-7, name is Methyl 4-bromo-3-methylbenzoate, This compound has unique chemical properties. The synthetic route is as follows., Formula: C9H9BrO2

Reference Example 11 [0605] [0606] A mixture of methyl 4-bromo-3-methylbenzoate (4.58 g), [1,1?-bis(diphenylphosphino)-ferrocene]dichloropalladium (II) (1.46 g), potassium carbonate (11.0 g) and 2-(trifluoromethyl)phenylboronic acid (7.60 g) was stirred in DMF (100 mL) at 80 C. for 24 hours. After cooling to room temperature, the reaction mixture was diluted with a mixed solvent of ethyl acetate-toluene (1:1) and filtered. Water was added to the filtrate and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine successively, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give a residue, which was purified with silica gel column chromatography (hexane/ethyl acetate) to give compound 11-1 (5.61 g). N-Bromosuccinimide (2.06 g) and benzoyl peroxide (133 mg) were added to a solution of compound 11-1 (3.07 g) in carbon tetrachloride (47 mL) and the mixture was heated to reflux for 6 hours. After cooling to room temperature, the reaction mixture was filtered. The filtrate was concentrated under reduced pressure and the resulting residue was purified with silica gel column chromatography (hexane/ethyl acetate) to give compound 11-2 (4.05 g) as a crude product. The crude product (3.78 g) of compound 11-2 was dissolved in acetic acid (73 mL), sodium acetate (4.17 g) was added thereto, and the mixture was heated to reflux for 16 hours. After cooling to room temperature, the reaction solution was concentrated under reduced pressure to give a residue, to which water was added and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine successively, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give a residue, which was purified with silica gel column chromatography (hexane/ethyl acetate) to give compound 11-3 (2.39 g). Compound 11-3 (2.04 g) was dissolved in a mixed solvent of tetrahydrofuran-methanol (1:1) (40 mL), 1N aqueous solution of sodium hydroxide (23 mL) was added dropwise thereto, and the mixture was stirred at room temperature for 25 hours. The reaction solution was acidified by addition of 2N aqueous solution of hydrochloric acid, concentrated under reduced pressure and ethyl acetate and 1N aqueous solution of hydrochloric acid were added. The organic layer was extracted, washed with saturated brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give a residue, which was azeotropically distilled with toluene to give compound 11-4 (1.69 g). Compound 11-5 (89 mg) was prepared from compound 11-4 (94 mg) in the same manner as the second step of Reference Example 9. Compound 11-1: 1H-NMR (CDCl3) delta 2.08 (s, 3H), 3.94 (s, 3H), 7.22 (d, J=8.1 Hz, 2H), 7.50 (t-like, J=7.6 Hz, 1H), 7.59 (t-like, J=7.1 Hz, 1H), 7.77 (d, J=7.7 Hz, 1H), 7.88 (md, J=7.9 Hz, 1H), 7.94 (m, 1H). Compound 11-2: 1H-NMR (CDCl3) delta 3.96 (s, 3H), 4.04 (d, J=10.4 Hz, 1H), 4.40 (d, J=10.4 Hz, 1H), 7.27 (d, J=8.1 Hz, 2H), 7.43 (d, J=7.3 Hz, 1H), 7.52-7.64 (m, 2H), 7.79 (d, J=7.3 Hz, 1H), 7.99 (dd, J=8.0, 1.7 Hz, 1H), 8.21 (d, J=1.7 Hz, 1H). Compound 11-3: 1H-NMR (CDCl3) delta 2.00 (s, 3H), 3.94 (s, 3H), 4.81 (AB q, JAB=22.8 Hz, 2H), 7.28 (d, J=7.9 Hz, 2H), 7.48-7.59 (m, 2H), 7.76 (d, J=7.2 Hz, 1H), 8.00 (dd, J=8.0, 1.7 Hz, 1H), 8.14 (d, J=1.3 Hz, 1H). Compound 11-4: 1H-NMR (CDCl3) delta 4.42 (AB q, JAB=23.0 Hz, 2H), 7.29 (d, J=8.1 Hz, 2H), 7.50-7.61 (m, 2H), 7.78 (d, J=7.5 Hz, 1H), 8.05 (dd, J=8.0, 1.6 Hz, 1H), 8.34 (s, 1H). [0607] Compound 11-5: 1H-NMR (CDCl3) delta 4.83 (AB q, JAB=20.4 Hz, 2H), 7.27 (d, J=7.5 Hz, 1H), 7.32 (d, J=8.0 Hz, 1H), 7.50-7.61 (m, 2H), 7.77 (d, J=7.2 Hz, 1H), 8.08 (dd, J=7.9, 1.8 Hz, 1H), 8.21 (d, J=1.7 Hz, 1H).

According to the analysis of related databases, 148547-19-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; DAINIPPON SUMITOMO PHARMA CO., LTD.; Katayama, Seiji; Hori, Seiji; Hasegawa, Futoshi; Suzuki, Kuniko; US2013/116227; (2013); 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. 57381-59-6, name is Methyl 5-bromo-2-fluorobenzoate, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of Methyl 5-bromo-2-fluorobenzoate

Methyl-5-benzyl-2-fluorobenzoate To a solution of methyl-5-bromo-2-fluorobenzoate (350 mg, 1 .5 mmol) in dioxane (20 ml_), was added sequentially 2-benzyl-4, 4,5, 5-tetramethyl-1 ,3, 2-dioxaborolane (327 mg, 1 .5 mmol), anhydrous potassium phosphate (955 mg, 4.5 mmol) and [1 ,1 ‘-bis(diphenylphosphino)ferrocene]palladium(ll) chloride (7 mg, 0.01 mmol) under an argon atmosphere. The mixture was stirred at 90C overnight before dioxane was concentrated under reduced pressure. The residue was purified by silica gel column chromatography eluting with ethyl acetate : petroleum ether = 1 :10 to afford methyl-5-benzyl-2-fluorobenzoate (350 mg, crude) as a colorless oil, which was used directly without further purification. LCMS (ESI): m/z = 245.1 [M+H]+.

According to the analysis of related databases, 57381-59-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; X-RX DISCOVERY, INC.; RUEBSAM, Frank; WANG, Ce; NI, Haihong; MULVIHILL, Mark, J.; BABISS, Lee; RENZETTI, Louis; ZHANG, Ying; (99 pag.)WO2015/175171; (2015); A1;,
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Adding a certain compound to certain chemical reactions, such as: 773134-11-5, name is Methyl 4-bromo-2,6-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 773134-11-5, Quality Control of Methyl 4-bromo-2,6-difluorobenzoate

4-Bromo-2,6-difluoro-benzoic acid methyl ester (250 mg, 1 mmol) was dissolved intriethylamine (5 mL) and dichloropalladium(bis)triphenylphosphine (36 mg, 0.05 mmol) was added followed by copper iodide (10 mg, 0.05 mmol) and cyclopropylacetylene (85 iL, 1.2 mmol). The reaction mixture was heated for 1 hour at 100 G under microwave radiation. The mixture was cooled to room temperature and filtered through DecaliteTM and concentrated under reduced pressure. The crude residue was purified by column chromatography (heptane to ethyl acetate = 9/1 v/v%) to afford 214mg of the title compound (yield: 90.6%).

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; NETHERLANDS TRANSLATIONAL RESEARCH CENTER B.V.; DE MAN, Adrianus Petrus Antonius; UITDEHAAG, Joost Cornelis Marinus; STERRENBURG, Jan Gerard; DE WIT, Joeri Johannes Petrus; SEEGERS, Nicole Wilhelmina Cornelia; VAN DOORNMALEN, Antonius Maria; BUIJSMAN, Rogier Christian; ZAMAN, Guido Jenny Rudolf; (88 pag.)WO2017/153459; (2017); 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. 75567-84-9, name is Methyl 3-(4-bromophenyl)propanoate, A new synthetic method of this compound is introduced below., Product Details of 75567-84-9

According to the following scheme, electrochromic compound 8 was synthesized.The flask was charged with the above intermediate 2-1 (3.92 g, 10 mmol), methyl 3- (4-bromophenyl) propionate (4.86 g, 20 mmol), sodium tert-butoxide (3.84 g, 40 mmol), palladium (67 mg, 0.3 mmol), and tri-tert-butylphosphonium tetrafluoroborate (261 mg, 0.9 mmol), and after purging with argon gas, ortho-xylene (40 mL) degassed with argon gas was added, And the mixture was heated and stirred at 115 C. for 3 hours. The reaction solution was returned to room temperature and filtered through Celite. Next, the filtrate was concentrated and purified by silica gel column chromatography (stationary phase: neutral silica gel, mobile phase: toluene) to obtain Intermediate 8-1 as a pale yellow solid (yield 5.23 g , Yield 73%).

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; RICOH COMPANY LIMITED; GOTO, DAISUKE; SAGISAKA, TOSHIYA; YAMAMOTO, SATOSHI; KANEKO, FUMINARI; INOUE, MAMIKO; YASHIRO, TOHRU; YUTANI, KEIICHIRO; NAGAI, KAZUKIYO; SHIMADA, TOMOYUKI; SHINODA, MASATO; (45 pag.)JP2016/138067; (2016); A;,
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Adding a certain compound to certain chemical reactions, such as: 1245643-11-1, name is Methyl 3,4-diamino-5-bromobenzoate, 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 1245643-11-1, Safety of Methyl 3,4-diamino-5-bromobenzoate

A 3M aqueous solution of NaOH (11.6 mL; 34.8 mmol) was added to a mixture of intermediates 3a and 3b (4.08 g; 11.6 mmol) in EtOH (60 mL) and THF (60 mL). The reaction mixture was stirred at rt overnight and evaporated under vacuum. The residue was acidified with a 0.5 N aqueous solution of HC1 to give a precipitate. The solid was filtered off, washed with water, then diethylether and dried under vacuum to give 3.86 g (99%o, yellow solid) of intermediate 4.

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 3,4-diamino-5-bromobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; ANGIBAUD, Patrick, Rene; QUEROLLE, Olivier, Alexis, Georges; BERTHELOT, Didier, Jean-Claude; MEYER, Christophe; WILLOT, Matthieu, Philippe, Victor; MEERPOEL, Lieven; JOUSSEAUME, Thierry, Francois, Alain, Jean; (114 pag.)WO2018/178280; (2018); A1;,
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Reference of 87-13-8, 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. 87-13-8, name is Diethyl 2-(ethoxymethylene)malonate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

2-Phenylaminomethylene-malonic acid diethyl ester: 2-(Ethoxymethylene)-malonic acid diethyl ester (50 mmol) and aniline (50 mmol) are mixed in a flask. The flask is sealed, and the mixture is heated to 1509C in a microwave reactor, stirred for 15 min and then cooled to rt. The crude oil is purified by flash-chromatography (cyclohexane / EtOAc 90 : 10) to yield the title compound in the form of a yellow, viscous oil.

The synthetic route of Diethyl 2-(ethoxymethylene)malonate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; WO2009/21961; (2009); A1;,
Ester – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 62638-06-6, name is Dimethyl cyclohexane-1,3-dicarboxylate, 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 62638-06-6, Quality Control of Dimethyl cyclohexane-1,3-dicarboxylate

REFERENCE EXAMPLE 72 Monomethyl 1,3-cyclohexanedicarboxylate In 85 ml of methanol were dissolved 8.33 g of dimethyl 1,3-cyclohexanedicarboxylate, and 41.6 ml of 1N aqueous sodium hydroxide solution was added thereto, and the resulting mixture was stirred at room temperature for 4 hours. The solvent was distilled off under reduced pressure and the aqueous solution was washed with ethyl acetate. The pH was adjusted to 1 with diluted hydrochloric acid under ice-cooling and extracted with ethyl acetate. The extracts were washed with an aqueous sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to obtain 6.7 g of the desired compound as a colorless oil. NMR spectrum (CDCl3) delta ppm: 1.20-2.45(9.3H,m), 2.65-2.80(0.7H,m), 3.68(3H,s)

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, Dimethyl cyclohexane-1,3-dicarboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Sankyo Company, Limited; US5843973; (1998); A;,
Ester – Wikipedia,
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Synthetic Route of 3044-06-2, The chemical industry reduces the impact on the environment during synthesis 3044-06-2, name is Diethyl 2-(1-ethoxyethylidene)malonate, I believe this compound will play a more active role in future production and life.

General procedure: Diethyl ethoxymethylenemalonate (4.6mmol) were add to a solution of sodium hydride (9.7mmol) and compound 14a-l (4.2mmol) in ethanol (20mL), the reaction mixture was stirred at 80C for 2h. After the reaction completed, the mixture was added 10mL 6M hydrochloric acid and stirred for 0.5h, then the precipitate was collected by filtration. The resulting residue was recrystallized from ethanol to yield ethyl 2-(4-alkoxyphenyl-3-cyano)-6-oxo-1,6-dihydropyrimidine-5-carboxylate(15a-l).

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, Diethyl 2-(1-ethoxyethylidene)malonate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Mao, Qing; Dai; Xu, Gaoyang; Su, Yu; Zhang, Bing; Liu, Dan; Wang, Shaojie; European Journal of Medicinal Chemistry; vol. 181; (2019);,
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