Month: July 2021

Synthetic Route of 24332-20-5, 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.

To a solution of 1,1,2-trimethoxyethane (132 mg, 0.46 mmol) in H2O (1 mL), was added TFA (1 mL). The reaction mixture was stirred at 50 for 5 min. The resulting colorless solution was used as such in the following step.

The chemical industry reduces the impact on the environment during synthesis 1,1,2-Trimethoxyethane. I believe this compound will play a more active role in future production and life.

Reference:
Patent; REMEDY PLAN, INC.; CRIMMINS, Gregory, Thomas; DE JESUS DIAZ, Dennise, Alexandra; BHURRUTH-ALCOR, Yushma; (483 pag.)WO2019/213570; (2019); A1;,
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Related Products of 36805-97-7,Some common heterocyclic compound, 36805-97-7, name is 1,1-Di-tert-butoxy-N,N-dimethylmethanamine, molecular formula is C11H25NO2, 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.

Hexadecanedioic acid (4.5 g, 15.71 mmol) was suspended in Toluene (28.1 ml) and the mixture was heated to reflux. 1,1 -di-tert-butoxy-N,Ndimethylmethanamine (10.10 ml, 42.1 mmol) was added drop-wise over 30 mm. Themixture was reflux overnight. The solvent was removed in vacuo at 50C and the crude material was suspended in CH2C12/EtOAc (75 mL. 1:1) ans stirred for 15 mm. The solids were removed by filtration and washed with CH2C12 (25 mL). The filtration was evaporated in vacuo. The resulting material was suspended in CH2C12 (6 mL), cooled with ice for 10 mins, and filtered. The solvent was removed invacuo to leave crude product which was purified by flash chromatography (silic gel,EtOAc/Hexane) to get 16-(tert-butoxy)-16-oxohexadecanoic acid (2.56 g, 7.47 mmol,47.6 % yield). Analysis condition D: Retention time = 5.04 mm; ESI-MS(+) m/z269.3 [M – OC(CH3)3]; ?H NMR (500MHz, METHANOL-d4) oe 2.33 – 2.18 (m, 4H),1.66 – 1.54 (m, 4H), 1.50 – 1.43 (m, 9H), 1.40 – 1.25 (m, 20H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,1-Di-tert-butoxy-N,N-dimethylmethanamine, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; GILLMAN, Kevin W.; GOODRICH, Jason; BOY, Kenneth M.; ZHANG, Yunhui; MAPELLI, Claudio; POSS, Michael A.; SUN, Li-Qiang; ZHAO, Qian; MULL, Eric; GILLIS, Eric P.; SCOLA, Paul Michael; LANGLEY, David, R.; (683 pag.)WO2016/77518; (2016); A1;,
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Reference of 366-99-4, A common heterocyclic compound, 366-99-4, name is 3-Fluoro-4-methoxyaniline, molecular formula is C7H8FNO, 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.

Step 1. To a mixture of 3-fluoro-4-methoxyaniline (3.00 g, 21.3 mmol) and paraformaldehyde (1.28 g, 42.5 mmol) in MeOH (100 mL) was added sodium methoxide (19.4 mL, 85.0 mmol) and the reaction mixture mixture was sealed and heated at 55 °C for 2 h. After cooling to rt, sodium borohydride (2.01 g, 53.1 mmol) was added in small portions. The final reaction mixture was stirred at rt overnight. The solvent was removed in vacuo and the residue was taken up in EtOAc (100 mL) and washed with water (150 mL). The separated aqueous component was saturated with NaCl, extracted with EtOAc (100 mL) and the combined organic components were washed with brine (50 mL), dried over MgS04, filtered, and concentrated in vacuo. The residue was taken up into DCM (10 mL) and purified by FCC (80 g silica gel cartridge), eluting with gradient 5percent~50percent EtO Ac- hexanes to afford 3-fluoro-4-methoxy-N-methylaniline (3.08 g) as a light yellow oil. LC- MS retention time = 1.34 min; m/z = 153.42 [M-H]-. (Start percent B = 0, Final percent B = 100, Gradient Time = 2 min, Flow Rate = 1 ml/min, Wavelength = 220, Solvent Pair = Water: Acetonitrile 10 mM Ammonium Acetate, Solvent A = 95percent Water: 5percent Acetonitrilel 10 mM Ammonium Acetate, Solvent B = 5percent Water: 95percent Acetonitrile 10 mM Ammonium Acetate, Column = Phenomenex Luna CI 8 2.0 X 30mm 3um, MW1 = 132+/- Oven Temp. = 40 °C).

The synthetic route of 366-99-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VIIV HEALTHCARE (No.5) LIMITED; BENDER, John A.; LOPEZ, Omar D.; NGUYEN, Van N.; YANG, Zhong; WANG, Alan Xiangdong; WANG, Gan; MEANWELL, Nicholas A.; BENO, Brett R.; FRIDELL, Robert A.; BELEMA, Makonen; THANGATHIRUPATHY, Srinivasan; (350 pag.)WO2016/172425; (2016); 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. 54314-84-0, name is ((3-Bromopropoxy)methyl)benzene, A new synthetic method of this compound is introduced below., Recommanded Product: 54314-84-0

The reaction mixture of 28 (0.50 g, 1.5 mmol) and [(3-bromopropoxy)methyl]benzene (32) (0.44 ml, 2.5 mmol) in dry 1,4-dioxane (16 ml) was stirred for 5 days to afford the title compound as a white solid in 73% yield (0.62 g). mp: 228-229 C; 1H-NMR (400 MHz, DMSO-d6): delta = 7.27-7.40 (m, 15H), 6.76 (s, 1H), 5.21 (br, 1H), 4.46 (s, 2H), 3.85 (m, 1H), 3.46 (t, J = 5.8 Hz 2H), 3.21-3.39 (m, 6H), 3.03 (m, 1H), 2.25 (m, 1H), 1.49-1.95 (m, 6H); 13C-NMR (500 MHz, DMSO-d6): delta = 172.8, 158.9, 143.6, 143.5, 130.1, 128.5, 128.4, 128.2, 128.1, 127.6, 127.5, 121.1, 115.0, 81.3, 69.1, 67.0, 63.0, 59.8, 54.1, 53.2, 26.2, 23.9, 20.9, 19.0, 18.1; HRMS calcd. for C31H36N1O4 [M]+: 486.2644; found: m/z = 486.2663; HPLC (Method B): tR (min) = 15.2 (98%).

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; Yamashita, Yasunobu; Tanaka, Ken-ichiro; Yamakawa; Asano; Kanda, Yuki; Takafuji; Kawahara, Masahiro; Takenaga, Mitsuko; Fukunishi, Yoshifumi; Mizushima; Bioorganic and Medicinal Chemistry; vol. 27; 15; (2019); p. 3339 – 3346;,
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Adding a certain compound to certain chemical reactions, such as: 62257-15-2, name is 2-Fluoro-5-methoxyaniline, 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 62257-15-2, Safety of 2-Fluoro-5-methoxyaniline

B. Ethyl 5-amino-1-(2-fluoro-5-methoxyphenyl)-1H-imidazole-4-carboxylate, 3b A solution of compound 3a (4.5 g, 35 mmol) and (diethoxymethoxy)ethane (6.3 g, 42 mmol) in CH3CN (50 mL) was stirred at 80 qC for 1 h. The reaction mixture was allowed to cool to RT and treated with 2-fluoro-5-methoxyaniline (3.0 g, 21 mmol). The resulting solution was stirred overnight at RT and concentrated. The residue obtained was purified by flash chromatography (0-25% EtOAc/petroleum ether) on silica gel to obtain compound 3b as a light yellow solid. Mass Spectrum (LCMS, ESI pos.): Calcd. for C13H14FN3O3: 280.1 (M+H); found: 280.0.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Fluoro-5-methoxyaniline, and friends who are interested can also refer to it.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; HUANG, Hui; MEEGALLA, Sanath; PLAYER, Mark R.; (196 pag.)WO2017/27310; (2017); A1;,
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Electric Literature of 36865-41-5, A common heterocyclic compound, 36865-41-5, name is 1-Bromo-3-methoxypropane, molecular formula is C4H9BrO, 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 mixture of 5-bromo-2-chloro-phenol (10.00 g, 48.20 mmol, 1.00 eq), 1-bromo-3- methoxy-propane (14.75 g, 96.41 mmol, 2.00 eq) and K2C03 (19.99 g, 144.61 mmol, 3.00 eq) in acetone (100.00 mL) was stirred at 50 C for 15 h. After filtration, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel chromatography eluted with PE to PE :EA=5: 1. 4-bromo- 1 -chloro-2-(3 -methoxypropoxy)benzene (13.40 g, 47.93 mmol, 99.44% yield) was obtained as a colorless oil which was confirmed by LC-MS and used directly in the next step. LC-MS: EW5403-239-P1ZO (M+H=278.9, M+2+H=280.9)

The synthetic route of 36865-41-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NEWAVE PHARMACEUTICAL INC.; CHEN, Yi; (81 pag.)WO2018/22282; (2018); A1;,
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Application of 36865-41-5,Some common heterocyclic compound, 36865-41-5, name is 1-Bromo-3-methoxypropane, molecular formula is C4H9BrO, 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 stirred solution of ethyl isonipecotate (22.0 grams, 140 mmol) in acetonitrile (250 mL) at room temperature was added cesium carbonate (97 grams, 298 mmol) followed by l-brom -3-methoxypropane (20 mL, 154 mmol) and the reaction mixture was heated to reflux for 4 hours. The reaction mixture was cooled to room temperature and filtered through a small pad of celite. The volatiles were removed under reduced pressure to obtain ethyl l-(3-methoxy propyl) piperidin-4-carboxylate (31.0 grams).Yield: 99 %.? – NMR (CDCI3): delta 4.12 (q, 2H), 3.41 (t, J = 6.4 Hz, 2H), 2.90 – 2.85 (m, 2H), 2.38 (t, J = 7.4 Hz, 2H), 2.34 – 2.20 (m, 1H), 2.05 – 1.93 (m, 2H), 1.92 – 1.85 (m, 2H), 1.80 – 1.70 (m, 4H), 1.23 (t, J = 7.1 Hz, 3H); Mass (m/z): 230 (M+H)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Bromo-3-methoxypropane, its application will become more common.

Reference:
Patent; SUVEN LIFE SCIENCES LIMITED; NIROGI, Ramakrishna; MOHAMMED, Abdul Rasheed; YARLGADDA, Suresh; RAVELLA, Srinivasa Rao; SHINDE, Anil Karbhari; KAMBHAMPATI, Ramasastri; ROAYALLEY, Praveen Kumar; JAYARAJAN, Pradeep; BHYRAPUNENI, Gopinadh; PATNALA, Sriramachandra Murthy; RAVULA, Jyothsna; JASTI, Venkateswarlu; WO2013/42135; (2013); A1;,
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Application of 59557-91-4, A common heterocyclic compound, 59557-91-4, name is 4-Bromo-2-methoxyaniline, molecular formula is C7H8BrNO, 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.

Step A:To a round bottom flask at room temperature, containing formic acid (85%, 27 rrsL, 624.4 mmoi) was added acetic anhydride (16 mL, 169.5 mmoi) dropwise. The reaction stirred for 45 min. followed by the dropwise addition of a solution of 4-bromo- 2-methoxyaniline (9.01 g, 44.6 mmoi) in THF (56 mL). The reaction mixture was quenched with ice-water after 23 h and the resulting precipitate was filtered to afford compound 100.1 (9.20 g, 90%) as a brown solid.

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; SCHERING CORPORATION; WO2009/76352; (2009); A1;,
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Synthetic Route of 36942-56-0,Some common heterocyclic compound, 36942-56-0, name is 2-Bromo-4-methoxy-1-methylbenzene, molecular formula is C8H9BrO, 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 compound 11 (100 mg, 0.21 mmol) and 3-methoxybenzeneboronic acid (49 mg, 0.32 mmol) in dioxane (5 mL) and H2O (0.5 mL) was added Na2CO3 (44 mg, 0.42 mmol) and LiCl (18 mg, 0.42 mmol). Under Ar, Pd(PPh3)4 (24 mg, 0.021 mmol) was added. The mixture was stirred for 12 h at 85C. Water was added. The resulting solution was extracted with ethyl acetate and washed with water and brine. The organic solution was dried over sodium sulfate, concentrated in vacuo. The residue was purified by silica gel chromatography (petroleum/ethyl acetate 5:1) to give 67 mg of 12 (yield: 75%) as a colorless liquid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Bromo-4-methoxy-1-methylbenzene, its application will become more common.

Reference:
Article; Huang, Jing; Guo, Bin; Chu, Wen-Jing; Xie, Xin; Yang, Yu-She; Zhou, Xian-Li; Chinese Chemical Letters; vol. 27; 1; (2016); p. 159 – 162;,
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Synthetic Route of 645-36-3, 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. 645-36-3, name is 2,2-Diethoxyethanamine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A three-neck flask was charged with Pd(OAc)2 (0.0182 mmol, 4.1 mg), BINAP (0.02 mmol, 12 mg) and NaO-t-Bu (1.274 mmol, 122 mg). The reaction mixture was stirred in toluene (20 mL) for 10 min at 80 C. A mixture of NH2CH2CH(OCH2CH3)2 (1.092 mmol, 159 muL) and the compound prepared as in Example 1 (0.91 mmol, 500 mg) in toluene (2 mL) was then slowly added dropwise via syringe to the reaction mixture. After addition, the mixture was heated at 80 C. with stirring for 2 h. The reaction mixture was cooled to room temperature. Et2O and water were added and the solution was partitioned between Et2O and water. The Et2O layer was washed with brine, dried over anhydrous Na2SO4 and concentrate to yield the title compound as a crude solid. The crude product was purified by column chromatography using 4:1 hexanes/EtOAc to yield the title compound as a colorless oil. [0215] 1H NMR (300 MHz, CDCl3) delta 7.12 (d, J=8.8 Hz, 1H), 6.53 (d, J=8.8 Hz, 1H) 6.38 (s, 1H), 4.68 (t, J=6.0 Hz, 1H), 3.80 (br, s, 1H), 3.75 (m, 2H), 3.60 (m, 2H), 3.22 (d, J=6.0 Hz, 2H), 2.91 (m, 2H), 2.50 (dd, J=18.0, 8.8 Hz, 1H), 2.42 (m, 1H), 2.35 (m, 1H), 2.20 (m, 1H), 2.151.94 (m, 3H), 1.721.38 (m, 6H), 1.25 (t, J=7.6 Hz, 6H), 0.98 (s, 3H) MS (m/z) M+Na (408), MH- (384).

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

Reference:
Patent; Sui, Zhihua; Zhang, Xuqing; US2005/4090; (2005); A1;,
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