Tag: M.W=100-200

Adding a certain compound to certain chemical reactions, such as: 321-28-8, name is 1-Fluoro-2-methoxybenzene, belongs to ethers-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 321-28-8, Recommanded Product: 321-28-8

Step 1: Preparation of 3′-fluoro-4′-methoxy-acetophenone. Acetyl chloride (51.0 g, 0.65 mol) was added dropwise to a stirred solution of aluminum chloride (80.0 g, 0.6 mol) and chloroform (750 mL), maintaining the temperature between 5-10 C. The mixture was stirred for 10 minutes at 5 C before the dropwise addition of 2-fluoroanisole (62.6 g, 0.5 mol). The mixture was stirred at 0-10 C. for 1 hour and poured into ice (1 L). The resultant layers were separated and the aqueous layer was extracted with dichloromethane (2*250 mL). The combined organic layers were washed with water (2*150 mL), dried over anhydrous MgSO4, filtered and concentrated in vacuo to a volume of 300 mL. Hexanes were added and a white solid formed which was isolated by filtration and air dried. This material was recrystallized from a mixture of dichloromethane and hexanes to afford material suitable for use in the next step (77.2 g, 92%): mp 92-94 C.

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; G.D. Searle & Co.; US6407140; (2002); B1;,
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Reference of 702-24-9, These common heterocyclic compound, 702-24-9, name is 4-Methoxy-N-methylbenzylamine, 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.

Place ethyl 6,8-dichloroimidazo[ 1 ,2-bj pyridazine-3 -carboxylate (3 g, 11.54mmol), 1-(4-methoxyphenyl)-N-methylmethanamine (2.267 g, 15.00 mmol), and N,NDiisopropylethylamine (DIPEA) (4.03 mL, 23.07 mmol) in a 100 mL round bottle flask along with THF (15 mL). It was sealed and heated to 80¡ãC for 6 hours. The reactionmixture was concentrated and purified with silica gel chromatography. The product came out when eluting with 35percent ethyl acetate in hexane. The fractions containing product was collected and concentrated to provide the product (3.7 g, 9.87 mmol, 86percent yield, 100percentpurity). LC retention time 1.06 mm [Al. MS (ES+) m/z: 375 (MH). ?H NMR (400MHz, CHLOROFORM-d):8.14 – 8.09 (m, 1H), 7.20 – 7.13 (m, 2H), 6.89 – 6.83 (m, 2H), 6.11 (s, 1H), 5.49 (s, 2H),4.44 (q, J=7.2 Hz, 2H), 3.84 – 3.77 (m, 3H), 3.17 (s, 3H), 1.42 (t, J=7.2 Hz, 3H)

Statistics shows that 4-Methoxy-N-methylbenzylamine is playing an increasingly important role. we look forward to future research findings about 702-24-9.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WEINSTEIN, David S.; DUNCIA, John V.; SPERGEL, Steven H.; (76 pag.)WO2018/93968; (2018); A1;,
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Electric Literature of 10103-06-7,Some common heterocyclic compound, 10103-06-7, name is 2,3-Dimethoxynaphthalene, molecular formula is C12H12O2, 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.

(a) 2,3-Dimethoxy-naphthalene-1-carbaldehyde n-Butyl lithium in hexane (1.6 N, 31.3 ml) was gradually added to a solution of 2,3-dimethoxynaphthalene (9.4 g) and N,N,N’,N’-tetramethylethylenediamine (7.4 ml) in ether (150 ml) under argon at 0 C. The reaction mixture was stirred at room temperature for two hours, cooled to 0 C. and DMF (7.3 g) in ether (20 ml) added. The reaction mixture was stirred at room temperature overnight and poured in ice water. The product was extracted with ether, washed with water, dried, evaporated and recrystallized from ether. Yield: 4.2 g. 1H-NMR (DMSO-d6, 400 MHz): 10.68 (s,1H, CHO), 8.95-8.97 (m, 1H), 7.87-7.89 (m,1H), 7.80 (s,1H), 7.49-7.51 (m,2H), 4.00 (s,6H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2,3-Dimethoxynaphthalene, its application will become more common.

Reference:
Patent; Baeckstroem, Reijo; Pystynen, Jarmo; Lotta, Timo; Ovaska, Martti; Taskinen, Jyrki; US2004/34011; (2004); A1;,
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Electric Literature of 6487-99-6, These common heterocyclic compound, 6487-99-6, name is 2-(3-Methylphenoxy)ethylamine, 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.

A solution of Example IB (25 mg, 0.08 mmol) in N,N-dimethylformamide (1.0 mL) was treated with a solution of 2-(3H-[l ,2,3]triazolo[4,5-]pyridin-3-yl)- l, 1 ,3,3- tetramethylisouronium hexafluorophosphate(V) (35 mg, 0.09 mmol) in N,N-dimethylformamide (0.5 mL). Then a solution of 2-(m-tolyloxy)ethanamine (12 mg, 0.08 mmol) in N,N- dimethylacetamide (0.15 mL) was added followed by N,N-diisopropylethylamine (0.037 mL, 0.21 mmol). The reaction was shaken at ambient temperature overnight and purified by HPLC (2-coupled C8 5 mupiiota 100 A columns 30 mm x 75 mm each, flow rate of 50 mL/minute, 5-90% gradient of acetonitrile in buffer (0.1 % trifluoroacetic acid in water)) to provide the title compound. JH NMR (400 MHz, DMSO-Patent; CALICO LIFE SCIENCES LLC; ABBVIE INC.; MARTIN, Kathleen, Ann; SIDRAUSKI, Carmela; PLIUSHCHEV, Marina, A.; FROST, Jennifer, M.; TONG, Yunsong; XU, Xiangdong; SHI, Lei; ZHANG, Qingwei, I.; XIONG, Zhaoming; SWEIS, Ramzi, Farah; DART, Michael, J.; MURAUSKI, Kathleen; (288 pag.)WO2019/90074; (2019); A1;,
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Electric Literature of 171290-52-1, 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. 171290-52-1, name is 3,5-Dimethoxyphenylacetylene, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a solution of the azide intermediate (0.1 mmol) in 0.2 mL of DMFin a microwave tube, CuSO4 (0.05 mmol) diluted in 50.0 muL of water,sodium ascorbate (0.025 mmol) and the alkyne (0.2 mmol) were added.The tube was sealed and the solution was irradiated (70 C, 150 W) for10 min and, then, TLC analysis showed the complete consumption ofthe starting material. The reaction was diluted with 15 mL of brine,extracted with ethyl acetate (3¡Á10 mL), dried by anhydrous Na2SO4and concentrated under reduced pressure. The resulting crude productwas purified by column chromatography on silica gel [hexane: ethylacetate, 60:40% (v/v)] yielding the expected product.

The chemical industry reduces the impact on the environment during synthesis 3,5-Dimethoxyphenylacetylene. I believe this compound will play a more active role in future production and life.

Reference:
Article; Zimmermann, Lara A.; de Moraes, Milene H.; da Rosa, Rafael; de Melo, Eduardo B.; Paula, Favero R.; Schenkel, Eloir P.; Steindel, Mario; Bernardes, Lilian S.C.; Bioorganic and Medicinal Chemistry; vol. 26; 17; (2018); p. 4850 – 4862;,
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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. 456-49-5, name is 1-Fluoro-3-methoxybenzene, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 1-Fluoro-3-methoxybenzene

The 3-fluoro anisole (15 g, 119 mmol) was placed in THF (300 mL) and cooled to about -78 C., and then n-BuLi (89 mL 1.6 M in hexanes) was added while maintaining the temperature at around -70 C. The mixture was stirred for about 15 minutes, and bromine (18.9 g, 119 mmol) was added over 10 minutes. The mixture was warmed to r.t. and stirred overnight. The mixture was quenched with water, diluted with ether (500 mL) and partitioned between water/ether (1/1 300 mL). The water layer was back extracted with ether (250 mL), and the combined organic fractions were dried, filtered and concentrated. The dark residue was distilled under house vacuum (product 115-130 C.) to recover about 13.8 g of the product as a gray oil (57%/).

According to the analysis of related databases, 456-49-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Briner, Karin; Doecke, Christopher William; Mancuso, Vincent; Martinelli, Michael John; Richardson, Timothy Ivo; Rothhaar, Roger Ryan; Shi, Qing; Xie, Chaoyu; US2004/82590; (2004); A1;,
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Some common heterocyclic compound, 216067-66-2, name is O-(2,4-Dimethoxybenzyl)hydroxylamine, molecular formula is C9H13NO3, 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. Formula: C9H13NO3

6-Amino-hexanoic acid (13.1 g, 100 mmoL) was dissolved in 10% aqueous Na2CO3 solution (300 mL), then dioxane (200 mL) was added to the above solution. Fmoc-CI (26 g, 110 mmoL) was added to the above mixture portion-wise, and the resultant reaction mixture was stirring for 12h. The mixture was extracted with ether (150 mL X 2), and the aqueous portion was acidified by 6N HCI. The mixture was filtered, and the solid was washed with water and dried to give 6- (9H-Fluoren-9-ylmethoxycarbonylamino)-hexanoic acid as a white solid (31 g, 81 %). 6- (9H-Fluoren-9-ylmethoxycarbonylamino)-hexanoic acid (9.17 g, 25 mmoL) and 0- (2, 4- dimethoxy-benzyl)-hydroxylamine (36 g, 26 mmoL) were dissolved in DCM (250 mL), then DCC (6.18 g, 30 mmoL) was added ortion-wise. The resultant mixture was stirred for 3h at room temperature, then cooled to 0C, filtered, and washed with DCM. The organic solution was evaporated to dryness to give the crude [5- (2, 4-dimethoxy- benzyloxycarbamoyl)-pentyl]-carbamic acid 9H-fluoren-9-ylmethyl ester. The crude ester was reacted with piperidine (5 mL) in MeOH (150 mL) at room temperature for12 h. The solution was evaporated and the residue was purified by flash chromatography (silica, EtOAc: MeOH = 5: 1). 6-Amino-hexanoic acid (2,4-dimethoxy- benzyloxy)-amide was obtained as a white solid (4.15 g, 56%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 216067-66-2, its application will become more common.

Reference:
Patent; S*BIO PTE LTD; WO2005/40101; (2005); A1;,
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Electric Literature of 29026-74-2, The chemical industry reduces the impact on the environment during synthesis 29026-74-2, name is 2-Isopropoxyaniline, I believe this compound will play a more active role in future production and life.

EXAMPLE 4 Ethyl 1,6-dihydro-2-methylthio-6-oxo-5-pyrimidinecarboxylate (15 g) and 2-(1-methylethoxy)aniline (11.5 g) are added to ethanol (100 ml), and the mixture is refluxed with stirring for 17 hours. After cooling, the precipitate is collected by filtration and recrystallized from DMF to give ethyl 1,6-dihydro-2-[2-(1-methylethoxy)anilino]-6-oxo-5-pyrimidinecarboxylate (8.5 g). M.p. 205-207 C. Elemental analysis for C16 H19 N3 O4: Calcd. (%): C, 60.56; H, 6.03; N, 13.24. Found (%): C, 60.73; H, 6.12; N, 13.40. IR numaxnujol cm-1: 3000-3300 (NH), 1720 (C=O), 1600 (C=O). NMR (DMSO-d6) delta: 1.34 (6H, d, J=7 Hz, OCH(CH3)2), 1.30 (3H, t, J=7 Hz, OCH2 CH3), 4.26 (2H, q, J=7 Hz, OCH2 CH3), 4.73 (1H, m, OCH(CH3)2), 6.86-7.30 (3H, m, Ar–H), 8.32 (1H, d, J-8 Hz, Ar–H), 8.53 (1H, s, C4 –H), 8.20-12.30 (2H, b, 2*NH). Mass m/e: 317 (M+).

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, 2-Isopropoxyaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Morishita Pharmaceutical Co. Ltd.; US4666915; (1987); 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. 24332-20-5, name is 1,1,2-Trimethoxyethane, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 1,1,2-Trimethoxyethane

A solution of 1,1,2-trimethoxyethane (838 mg, 6.9 mmol, 901.3 uL) in water (22.0 mL) and HC1 (0.3 mL, 2M) was stirred at 60C for 2h, then extracted with dichloromethane (10.0 mL x 3). The combined organic layers were washed with brine (30.0 mL x 3), dried over Na2 SO4, filtered to give a filtrate. To the filtrate was added the solution of 2-((lr,4r)-4- aminocyclohexyl)isoindoline-1,3-dione (500 mg, 1.4 mmol, TFA) with TEA to pH 7 in MeOH (30.0 mL) and CH3COOH (125 mg, 2.0 mmol, 119.7 uL). And then NaBH3CN (175 mg, 2.7 mmol) was added to above reaction mixture and CH3COOH was added to adjusted pH to 5. The mixture was stirred at 60C for 12 h. The reaction mixture was extracted with dichloromethane (30.0 mL x 3). The combined organic layers were washed with brine (30 mL x 3), dried over Na2SO4, filtered and concentrated under reduced pressure to give 2-((lr,4r)-4-((2- methoxyethyl)amino)cyclohexyl)i soindoline- 1,3 -dione (410 mg, crude).

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 24332-20-5.

Reference:
Patent; QUENTIS THERAPEUTICS, INC.; VACCA, Joseph P.; LI, Dansu; BETTIGOLE, Sarah; (143 pag.)WO2018/222917; (2018); 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. 702-24-9, name is 4-Methoxy-N-methylbenzylamine, A new synthetic method of this compound is introduced below., SDS of cas: 702-24-9

General procedure: A solution of 2-methyl-4-chlorocyclopenta[d]pyrimidine (17, 1eq.) and appropriate anilines or benzylamines (1.05 eq.) wereplaced in dioxane in a microwave vial. To the solution, HCl (2Nin dioxane, 1?2 drops) was added. The reaction mixture was setin a Biotage microwave initiator at 120 C for 3?6 h with pressure<4 bar. The reaction was cooled and transferred to a flask, and thesolvent was evaporated at reduced pressure. The residue wasdiluted with EtOAc, neutralized with NH4OH, and then washedwith water (2 10 mL). After drying with anhydrous Na2SO4, theorganic solvent was concentrated in a rotary evaporator to <1mL. This residue was placed on top of a silica gel column and elutedwith hexane and EtOAc or with CHCl3 and MeOH. Fractions containingthe product (TLC) were pooled and evaporated to affordpure compounds 3?7, 9?14. 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; Xiang, Weiguo; Choudhary, Shruti; Hamel, Ernest; Mooberry, Susan L.; Gangjee, Aleem; Bioorganic and Medicinal Chemistry; vol. 26; 9; (2018); p. 2437 – 2451;,
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