Month: May 2021

Synthetic Route of 36805-97-7, These common heterocyclic compound, 36805-97-7, name is 1,1-Di-tert-butoxy-N,N-dimethylmethanamine, 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.

Preparation GW-(2,6-diethylphenyl)-5-[(2E)-3-(dimethyta [(VI) R2 =Me, R3 = CONHR”, R” = 2,6-diethylphenyl]step 5To a solution of 5-acetyl-/V-(2,6-diethylphenyl)-1-methyl-1 H-pyrazole-3-carboxamide (0.013 g, 0.043 mmol) in DMF (1.5 mL), A/,A/-dimethylformamide di-tertbutyl acetal (0.0.63 mL, 0.650 mmol) was added. The mixture was stirred at 80C for 2 h. The reaction was diluted with water, extracted with AcOEt (2×20 mL). The organic fractions were combined, dried over Na2S04, filtered, and concentrated in vacuo and the residue used without any further purification. (0.017g, 78% yield).1H NMR (400 MHz, DMSO-d6) delta ppm 9.58 (s, 1 H), 7.71 (d, J =12.33 Hz, 1 H), 7.36 (s, 1 H), 7.21 (t, J =7.60 Hz, 1 H), 7.12 (d, J =7.60 Hz, 2 H), 5.75 (d, J =12.33 Hz, 1 H), 4.18 (s, 3 H), 3.16 (s, 3 H), 2.92 (s, 3 H), 2.52 (q, J =7.57 Hz, 4 H), 1.09 (t, J =7.57 Hz, 6 H)HRMS (ESI) calcd for C20H27N4O2 [M +H]+ 355.2129, found 355.2133.

The synthetic route of 36805-97-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NERVIANO MEDICAL SCIENCES S.r.l.; CASUSCELLI, Francesco; BRASCA, Maria Gabriella; CALDARELLI, Marina; CERVI, Giovanni; DISINGRINI, Teresa; QUARTIERI, Francesca; WO2012/139930; (2012); A1;,
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Some common heterocyclic compound, 944317-92-4, name is 1-Bromo-4-fluoro-5-isopropyl-2-methoxybenzene, molecular formula is C10H12BrFO, 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: C10H12BrFO

General procedure: A 500 mL dry flask was charged with 1-bromo-4-fluoro-5-isopropyl-2-methoxybenzene (BrMIP) (24.60 g, 0.10 mol) and dissolved in toluene (80 mL) and THF (80 mL). The resulting solution was flushed with argon, and tri- isopropylborate (32 mL, 0.1 mol) was added. The mixture was cooled to -80 C. Then 2.5 n-BuLi in hexanes (48 mL, 0.12 mol) was added slowly, maintaining a temperature below -55C. After completion of the n-BuLi addition, the reaction mixture was slowly warmed (1 hour) to -10C and water (120 mL) was added, followed by commercially available 2-bromo-5-(trifluoromethyl)benzonitrile (Formula VI’, X = Br, R2 = CN) (25.00 g, 0.10 mmol) and the catalyst, 1 , 1 bis( di-tertbutylphosphino)ferrocene palladium dichloride (265 mg, 0.8 mol%) addition. The organic layer turns dark brown immediately. The biphasic mixture is aged at room temperature with vigorous stirring for 12 hours. The aqueous layer was removed and the organic layer was washed with 1 M NaOH (aq) (100 mL), water (300 mL) and filtered through silica gel. The solvent was removed under reduced pressure to yield brown oil which was crystallized from EtOH/water (300/100 mL). The resulting slurry was filtered and the filter cake was washed with cold 50% EtOH. The product was dried at 40 C under vacuum to yield 4′-fluoro-5′- isopropyl-2′-methoxy-4-(trifluoromethyl)biphenyl-2-carbonitrile (Formula VII’, Ri = CN, R2 = isopropyl) as a pale white solid (25.20 g, 75%). According to the same procedure in various scales and different concentrations of catalyst some other biaryl of Formula Vlh and Vll2 are prepared and listed in Table 3 and Table 4, respectively. For NMR data and melting points see Table 1 and 2.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 944317-92-4, its application will become more common.

Reference:
Patent; LEK PHARMACEUTICALS D.D.; HUMLJAN, Jan; MARAS, Nenad; WO2013/91696; (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. 41365-75-7, name is 1-Amino-3,3-diethoxypropane, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 1-Amino-3,3-diethoxypropane

3,3-diethoxypropan-1-amine (1) (5.24 g, 35.6 mmol) was diluted in a mixture of dichloromethane (80 mL) and triethylamine (5.12 mL). The solution was cooled to 0 C., and a solution of di-tert-butyl-dicarbonate (7.85 g, 35.97 mmol) in dichloromethane (20 mL) was slowly added over a 15-minute period. The mixture was stirred for 16 h, at room temperature. The organic phase was washed with 1N HCl (1×100 mL), 0.5N HCl (1×100 mL), and brine (2×100 mL) before it was dried with anhydrous magnesium sulphate, filtered and concentrated. Le crude product was purified by flash chromatography on silica gel (eluent:hexanes/ethyl acetate 7:3). The protected amine was obtained as a yellow oil (8.36 g, 94%). 1H NMR (300 MHz, CDCl3) delta (ppm) 4.93 (s, 1H), 4.53 (t, 1H, J=5.5 Hz), 3.56 (d-quint, 4H, J=38.9 Hz, J=2.3 Hz), 3.20 (q, 2H, J=6.2 Hz), 1.79 (q, 2H, J=6.2 Hz), 1.42 (s, 9H), 1.19 (t, 6H, J=7.1 Hz). 13C NMR (75.5 MHz, CDCl3) delta (ppm) 155.9, 101.9, 78.9. 61.5, 36.7, 33.4, 28.4, 15.3. IR (CHCl3) v (cm-1) 3363 (br), 2979, 2920, 2880, 1708, 1514, 1448, 1393, 1365, 1171, 1139, 1065.

According to the analysis of related databases, 41365-75-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SOCPRA SCIENCES SANTE ET HUMAINES S.E.C.; Day, Robert; Neugebauer, Witold A.; Dory, Yves; (40 pag.)US9809621; (2017); B2;,
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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. 1515-81-7, name is 1-Methoxy-4-(methoxymethyl)benzene, A new synthetic method of this compound is introduced below., Quality Control of 1-Methoxy-4-(methoxymethyl)benzene

General procedure: Toan oven-dried round-bottomed flask under N2 atmosphere was added CH2Cl2(5 mL), the ketone (1.0 mmol), 2,6-lutidine (164 mL, 151 mg, 1.40 mmol) and TMSOTf (271 muL, 333 mg, 1.50mmol). The mixture was cooled to 0 Cand p-methoxybenzyl methyl ether (167mL, 167 mg, 1.10 mmol) was added. The reaction mixture was allowed to warmslowly to ambient temperature and stirred for 16 h, then it was passed througha column of silica (2 cm x 1 cm) with Et2O. The solvent was removedin vacuo and the residue was purified by column chromatography (0-5%EtOAc/hexanes).

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; Downey, C. Wade; Covington, Sarah E.; Obenschain, Derek C.; Halliday, Evan; Rague, James T.; Confair, Danielle N.; Tetrahedron Letters; vol. 55; 37; (2014); p. 5213 – 5215;,
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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. 6943-97-1, name is 1-(3-Bromopropyl)-3-methoxybenzene, A new synthetic method of this compound is introduced below., HPLC of Formula: C10H13BrO

Step C Preparation of 2-[3-(3-Methoxy-phenyl)-propyl]-malonic acid diethyl ester Diethylmalonate (7.65 mL, 0.050 mol) was added slowly to a vigorously stirred suspension of pre-washed NaH (60%) (2.4 g, 0.050 mol) in dry DMF (50 mL) at 0 C. under Ar. After 15 min, 3-(3-methoxyphenyl)propylbromide (11.5 g, 0.050 mol) was added slowly, the ice bath was removed, and the reaction mixture was stirred at 65 C. for 16 hr. The mixture was cooled, partitioned between EtOAc (250 mL) and H2O (200 mL), the organic layer washed with H2O (2*500 mL), dried (Na2SO4), filtered, and concentrated to dryness to give the title compound. FAB MS(M+1) 309.1

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; deSolms, S. Jane; Stokker, Gerald E.; Shaw, Anthony W.; US2002/99007; (2002); 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. 6358-77-6, name is 5-Bromo-2-methoxyaniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Product Details of 6358-77-6

Roundbottom flask is charged with 5-bromo-2-methylaniline ( 1000 mg; 5.37 mmol; 1.0 eq.) and formic acid( 1.22 ml32.25 mmol; 6.0 eq.). RM is cooled down to 0 C and sodium formate ( 73.11 mg; 1.07 mmol; 0.2 eq.) is added in this temperature. RM is stirred at room temperature for 2 h. After this time RM is diluted with DCM and sodium formate is filtered off. Filtrate is washed, with water and saturated aqueous solution of NaHC03.0rganic solvent is dried over anhydrous Na2S04 overnight. After this organic solvent is evaporated to afford N-(5-bromo-2-methylphenyl)formamide ( 869.50 mg; yield 68.8 %; 91.0 % by UPLC) as a brown solid.

The synthetic route of 6358-77-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SELVITA S.A.; FABRITIUS, Charles-Henry Robert Yves; NOWAK, Mateusz Oktawian; WIKLIK, Katarzyna Anna; SABINIARZ, Aleksandra Barbara; BIE?, Marcin Dominik; BUDA, Anna Ma?gorzata; GUZIK, Pawel Szczepan; JAKUBIEC, Krzysztof Roman; MACIUSZEK, Monika; KWIECI?SKA, Katarzyna; TOMCZYK, Mateusz Micha?; GA??ZOWSKI, Micha? Miko?aj; GONDELA, Andrzej; DUDEK, ?ukasz Piotr; (681 pag.)WO2016/180536; (2016); 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 886762-08-9 as follows. category: ethers-buliding-blocks

Into a 250-mL 3-necked round-bottom flask, was placed 5-bromo-2- (trifluoromethoxy) aniline (2 g, 7.81 mmol, 1 equiv), ethanol (20 mL), HCl (2 mL). This was followed by the addition of NaN02 (595 mg, 8.62 mmol, 1.10 equiv) dropwise with stirring at 0 C. To this was added water (110 mL), sulfuric acid (5.5 mL). The resulting solution was stirred for 1.5 h at 0 C in a water/ice bath. The resulting solution was allowed to react, with stirring, for an additional 12 h while the temperature was maintained at 100 C in an oil bath. The resulting solution was extracted with 3×100 mL of ethyl acetate and the organic layers combined. The resulting mixture was washed with 3×50 mL of sodium bicarbonate. The mixture was dried over anhydrous sodium sulfate. This resulted in 1 g (50%) of the title compound as an oil. Analytical Data: LC-MS: (ES, m/z): RT =1.715min, LCMS 53: m/z = 257 [M+l].

According to the analysis of related databases, 886762-08-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; EPIZYME, INC.; CAMPBELL, John Emmerson; DUNCAN, Kenneth William; FOLEY, Megan Alene; HARVEY, Darren Martin; KUNTZ, Kevin Wayne; MILLS, James Edward John; MUNCHHOF, Michael John; (586 pag.)WO2017/181177; (2017); A1;,
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Adding a certain compound to certain chemical reactions, such as: 707-07-3, name is (Trimethoxymethyl)benzene, 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 707-07-3, Application In Synthesis of (Trimethoxymethyl)benzene

To a solution containing diol 2 (7.1 g, 49.6 mmol) and trimethyl orthobenzoate (15 ml, 87.3 mmol) in chloroform (150 ml), was added camphor sulphonic acid (500 mg), and the reaction mixture was concentrated to 1/3 of its original volume using a rotavap; TLC revealed that the reaction is not finished, so more chloroform (-100 ml) was added to the mixture, and the solution was concentrated to its 1/3 volume again. This cycle was repeated until TLC indicates the complete consumption of starting material (usually 3-4 cycle needed). Et3N (1 ml) was added to the reaction mixture and the solvent was removed completely; the resulting syrup was treated with a 20% [ACOH-H20] solution (140 ml). After 30 min, the reaction was concentrated to dryness. The syrupy mixture was purified by column chromatography on silica gel using 5% AcOEt-toluene to afford 20 (6.17 g, 50%) and 21 (5.47 g, 44. [6%).’H] NMR (CDCl3, 600 MHz) for 20: [88.] 03 (m, 2H, Bz), 7.55 (m, [1H,] Bz), 7.43 (m, 2H, Bz), 5.94 (ddd, 1H, [J6.] 4,10. 6,17. 0 Hz, H-4), 5.41 (ddd, 1H, J 1.3, 1.3, 17.2 Hz, [H-5_TRANS),] 5.31 (ddd, 1H, J 1.3, 1.3, 10.4 Hz, H-5_cis), 4.57 (dd, [J3.] 7,11. 9 Hz, [H-LA),] 4.42 (dd, 1H, [J 7.] 7,11. 7 Hz, H-lb), 4.28 (m, 1H, H-3), 3.80 (ddd, 1H, J 3.5, 5.3, 7.7 Hz, [H-2). H] NMR (CDC13,600 MHz) for 21: [88.] 05 (m, 2H, Bz), 7.57 (m, 1H, Bz), 7.44 (m, 2H, Bz), 5.97 (ddd, [1H,] J 7.0, 10.6, 17.4 Hz, H-4), 5.66 (m, 1H, H-3), 5.48 (ddd, 1H, J 1.1, 1.1, 17.2 Hz, H- 5trans), 5.31 (ddd, [1H,] [J0.] 9,0. 9,10. 6 Hz, H-5_cis), 3. 83 (ddd, 1H, [J4.] 4,7. 1,9. 2 Hz, H-2), 3. 78 (dd, [J3.] 7,11. 9 Hz, [H-LA),] 4.42 (dd, 1H, [J7.] 7,11. 7 Hz, H-lb),

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; BUNDLE, David, R.; LING, Chang, Chun; ZHANG, Ping; WO2003/101937; (2003); 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. 111-95-5, name is Bis(2-methoxyethyl)amine, A new synthetic method of this compound is introduced below., Computed Properties of C6H15NO2

Example 391: N-[[6-[(4-Chlorophenylsulfonyl)(2,5-difluorophenyl)methyl]pyridin-3-yl]methyl]bis(2-methoxyethyl)amine After the [6-[(4-chlorophenylsulfonyl)(2, 5-difluorophenyl)methyl]pyridin-3-yl]carbaldehyde (100 mg, 0.245 mmol) obtained in Example 335, bis(2-methoxyethyl)amine (70 mg, 0.53 mmol) and acetic acid (0.029 ml, 0.51 mmol) were dissolved in 1,2-dichloroethane (5 ml), sodium triacetoxyborohydride (115 mg, 0.515 mmol) was added to the resulting solution at room temperature.. The resulting mixture was stirred at room temperature for 3 days.. A saturated aqueous solution of sodium bicarbonate and ethyl acetate were added to the reaction mixture.. The mixture was separated and the organic layer thus obtained was washed successively with a saturated aqueous solution of sodium bicarbonate and brine and dried over anhydrous magnesium sulfate.. After filtration, the filtrate was concentrated under reduced pressure.. The residue was subjected to flash silica gel chromatography and a fraction obtained from the elution portion with hexane:ethyl acetate = 3:2 was concentrated under reduced pressure to yield a white solid.. The solid was washed with hexane, whereby the title compound (101 mg, 0.192 mmol, 78%) was obtained as a white powder.1H-NMR (400 MHz, CDCl3) delta: 2.73 (4H, t, J = 5.8 Hz), 3.31 (6H, s), 3.47 (4H, d, J = 5.8 Hz), 3.75 (2H, s), 5.93 (1H, s), 6.88-6.97 (1H, m), 6.97-7.07 (1H, m), 7.38 (2H, d, J = 8.8 Hz), 7.50-7.60 (3H, m), 7.76 (1H, dd, J = 8.1, 2.0 Hz), 7.98-8.08 (1H, m), 8.54 (1H, d, J = 2.0 Hz). MS m/z: 525 (M++H).

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; DAIICHI PHARMACEUTICAL CO., LTD.; EP1466898; (2004); A1;,
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Application of 801282-00-8, The chemical industry reduces the impact on the environment during synthesis 801282-00-8, name is 2-Fluoro-3-methoxyaniline, I believe this compound will play a more active role in future production and life.

2,2-dimethyl-l ,3-dioxane-4,6,-dione (4.58 g, 31.78mmol) in trimethyl orthoformate (27.3mL, 245.9 mmol) was refiuxed at 100 C for 1 hr. 2-fluoro-3-methoxyaniline (3.9 g, 27.63 mmol) was then added and refluxing was continued for an additional hour. The reaction was cooled to room temperature and the suspension was filtered. The solid was washed with MeOH (60 mL) and dried under vacuum to yield the title compound. XH NMR H20438-004-04 (400MHz, chloroform-d) delta= 1 1.36 – 1 1.38 (m, 1H), 8.63-8.60 (m, 1H), 7.26- 6.83 (m, 3H), 3.92 (s, 3H), 1.75 (s, 6H).

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-Fluoro-3-methoxyaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK SHARP & DOHME CORP.; CALDWELL, John, P.; CAPLEN, Mary Ann; CUMMING, Jared, N.; DYKSTRA, Kevin, D.; HRUZA, Alan; LANKIN, Claire; LI, Derun; LIU, Hong; MCCRACKEN, Amy; MCKITTRICK, Brian; RAO, Ashwin; TAGAT, Jayaram, R.; TANG, Haiqun; TAOKA, Brandon, M.; VERRAS, Andreas; WALSH, Shawn, P.; WU, Wen-Lian; ZHANG, Tianyuan; (132 pag.)WO2018/34917; (2018); A1;,
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