Month: July 2021

Some common heterocyclic compound, 6346-09-4, name is 4,4-Diethoxybutan-1-amine, molecular formula is C8H19NO2, 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. Computed Properties of C8H19NO2

4-Amino-butyraldehyde diethyl acetal (8.0 g, 0.050 mol) was Fmoc protected following Procedure 10 to give the desired N-Fmoc-4-amino-butyraldehyde diethyl acetal (22.08 g, MS m/e [M+Na]+ calcd 406.2, found 406.1), which was carried through to the next step without further purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6346-09-4, its application will become more common.

Reference:
Patent; ACHAOGEN, INC.; AGGEN, James, Bradley; DOZZO, Paola; GOLDBLUM, Adam, Aaron; HILDEBRANDT, Darin, James; KANE, Timothy, Robert; GLIEDT, Micah, James; LINSELL, Martin, Sheringham; WO2011/44538; (2011); A1;,
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Reference of 33311-29-4, 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. 33311-29-4, name is 4-(2-Methoxyethoxy)aniline, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of (R)-3-(4-oxo-piperidin-1-yl)-butyronitrile (492 mg, 2.95 mmol) and 4-(2-methoxy-ethoxy)-phenylamine (492 mg, 2.95 mmol) in CH2Cl2 (12 mL) and glacial AcOH (14 drops) was added NaBH(OAc)3 (758 mg, 3.58 mmol) and the reaction stirred at room temperature overnight. Purification of the crude product by column chromatography on silica gel (CH2Cl2/MeOH, 96:4) gave the desired aniline (R)-3-{4-[4-(2-methoxy-ethoxy)-phenylamino-piperidin-1-yl}-butyronitrile (0.72 g, 94%) as an orange oil.

The chemical industry reduces the impact on the environment during synthesis 4-(2-Methoxyethoxy)aniline. I believe this compound will play a more active role in future production and life.

Reference:
Patent; AnorMED Inc.; US2005/277668; (2005); 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. 701-56-4, name is 4-Methoxy-N,N-dimethylaniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Formula: C9H13NO

General procedure: Under an atmosphere of N2, KOt-Bu (2.2 mmol), dioxane (0.9 mL), DMSO (1.65 mmol), tertiary amine 1 (0.55 mmol), and aryl halide 2 (1.65 mmol) were successively added to a Schlenk reaction tube. The mixture was stirred vigorously at 80-120 C for 12 h. Then the mixture was diluted with EtOAc, washed with sat. brine, and dried (anhyd Na2SO4). Then the solvent was removed under reduced pressure andthe residue was purified by flash column chromatography (petroleum ether and petroleum ether-EtOAc, 100:1 for the methoxy group derived products) to give pure products 3.

The synthetic route of 701-56-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Huang, Pei; He, Bang-Yue; Wang, Hui-Min; Lu, Jian-Mei; Synthesis; vol. 47; 2; (2015); p. 221 – 227;,
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Reference of 157869-15-3, 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 157869-15-3 as follows.

General experimental procedure for tandem addition-cyclization of 2-alkynylbenzenamines (1) with CS2: A solution of 2-alkynylbenzenamines 1 (0.30 mmol), CS2 (3.0 mmol, 10 equiv), AgNO3 (5 mol %), DABCO (1.2 equiv) in DMF (2.0 mL) was stirred at room temperature. After completion of reaction as indicated by TLC, the reaction was quenched with water (10 mL), extracted with EtOAc (2×10 mL), and dried by anhydrous Na2SO4. Evaporation of the solvent followed by purification on silica gel provided the corresponding 4-benzylidene-4H-benzo[d][1,3]thiazine 2a.

According to the analysis of related databases, 157869-15-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Ding, Qiuping; Liu, Xianjin; Yu, Jinsheng; Zhang, Qiulan; Wang, Dan; Cao, Banpeng; Peng, Yiyuan; Tetrahedron; vol. 68; 21; (2012); p. 3937 – 3941;,
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Adding a certain compound to certain chemical reactions, such as: 101-55-3, name is 1-Bromo-4-phenoxybenzene, 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 101-55-3, HPLC of Formula: C12H9BrO

(2) In a 500 ml four-necked flask, 3 g of 4-bromobiphenyl ether and 61 g of diethyl ether and 3.3 g of magnesium wire were put into a 500 ml four-necked flask under the protection of high-purity nitrogen, and Grignard reaction was initiated by rapid stirring at 35 C.,8 ~ 9 hours dropping 4-bromo-diphenyl ether 28g and80g ether solution,40 incubated for 2 hours, cooled to 5 , quickly added mixed coupling agent (cuprous iodide 1.5g, cuprous bromide 1.0g), continue to cool to -16 , temperature -16 ~ 20 ,(15 g of S-epichlorohydrin and 18 g of diethyl ether) was added dropwise for 10 to 11 hours and then incubated at -16 to 20 C for 15 hours, transferred to 65 g of 12% dilute sulfuric acid and stirred at 25 to 30 C for 1 hour,After standing for half an hour, the layers were separated and the ether was distilled and recovered. 120 g of water was added and the mixture was filtered while cooling to 5 C. The wet product was dried at 75 C for 2 hours to obtain (S) -1- (4-diphenylether) -2- Hydroxy-3-chloropropane yield 91.8%, content 95.1%. .

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; Binhai Extensive Chemical Co., Ltd.; Wu Fucai; (8 pag.)CN106957220; (2017); A;,
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Some common heterocyclic compound, 588-96-5, name is p-Bromophenetole, 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. Product Details of 588-96-5

To a solution of 4-bromophenetole (1.86 mL, 13.0 mmol) in anhydrous THF (15 mL) was added dropwise (over a 5-min period) a solution of n-BuLi (6.0 mL, 2.5 M in hexane) under nitrogen atmosphere at -78 C. The resulting mixture was stirred at -78 C for 1 hour, and then a solution of the Weinreb amide 43 (1.85 g, 10.0 mmol) in anhydrous THF (5.0 mL) was added dropwise (over a 10-min period). The reaction mixture was allowed to warm to room temperature and stirred for 16 hours. The mixture was poured into a 1 M HC1 solution (25 mL) and extracted with EtOAc (50 mL). The organic phase was subsequently washed with brine, dried over MgS04 and evaporated under vacuum. The residue was further purified by silica column chromatography (Biotage) to provide (4- ethoxyphenyl)(3-methylthiophen-2-yl)methanone (44, 1.52 g, 6.16 mmol, 62 %). NMR (400 MHz, CDC13) delta 7.84 (d, J = 8.8 Hz, 2H), 7.45 (d, J = 5.2 Hz, 1H), 7.98 (d, J = 4.8 Hz, 1H), 6.94 (d, J – 9.2 Hz, 2H), 4.1 1 (q, J = 6.8 Hz, 2H), 2.40 (s, 3H), 1.45 (t, J= 6.8 Hz, 3H); MH+ 247.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 588-96-5, its application will become more common.

Reference:
Patent; GREEN CROSS CORPORATION; LEE, Jinhwa; SONG, Kwang-Seop; LEE, Suk Ho; WO2012/33390; (2012); A2;,
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Electric Literature of 91-16-7, These common heterocyclic compound, 91-16-7, name is 1,2-Dimethoxybenzene, 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 type B crystal of 2,3,6,7,10,11-hexahydroxytriphenylene monohydrate was synthesized according to the process described in Synthesis, 477, 1994 and JP-A-8-119894. Namely, 1,2-dimethoxybenzene (31.78 g, 0.23 moles) and anhydrous ferric chloride (120 g, 0.74 moles) were dissolved in 70% sulfuric acid, and the solution was reacted at 25C for 24 hours with stirring. After completion of the reaction, the solution was poured into ice water (500 g), and the precipitated crystal was collected by filtration. After the resultant crystal was washed with water (1 L), and then dried to give pale purple colored 2,3,6,7,10,11-hexamethoxytriphenylene (28.2 g, theoretical yield from 1,2-dimethoxybenzene: 90.1%) (the method of Synthesis, 477, 1994).

The synthetic route of 91-16-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Wako Pure Chemical Industries, Ltd.; EP2177495; (2010); A1;,
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Adding a certain compound to certain chemical reactions, such as: 22236-10-8, name is 4-(Difluoromethoxy)aniline, 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 22236-10-8, COA of Formula: C7H7F2NO

5.1 Methyl 4-({[2-{(3R)-3-[(tert-butoxycarbonyl)amino]piperidin-1-yl}-1-(2-chlorobenzyl)-4-iodo-1H-imidazol-5-yl]carbonyl}amino)benzoate (5t) To a solution of 4 (56.08 g, 100 mmol) in CH2Cl2 (1.3 L) were added (COCl)2 (16.5 g, 130 mmol) and DMF (5 ml) at 0 C. The reaction mixture was stirred at room temperature for 4 h and concentrated under reduced pressure. The residue was azeotroped with toluene and redissolved in toluene (1.3 L). To this solution was added DIPEA (38.8 g, 300 mmol) followed by methyl 4-aminobenzoate (19.7 g, 130 mmol). The reaction mixture was stirred at room temperature for 12 h. The reaction mixture was then quenched with saturated NH4Cl aqueous solution, extracted with EtOAc, washed with brine, dried over Na2SO4, and concentrated under reduced pressure. The residue was purified by silica-gel column chromatography to give 5t (54.63 g, yield 79%) as a white amorphous. 1H NMR (300 MHz, CDCl3) delta 8.30 (br s, 1H), 8.01 (d, J = 8.7 Hz, 2H), 7.62 (d, J = 8.7 Hz, 2H), 7.39-7.36 (m, 1H), 7.22-7.13 (m, 2H), 6.82-6.78 (m, 1H), 5.58 (d, J = 16.2 Hz, 1H), 5.50 (d, J = 16.2 Hz, 1H), 4.93-4.90 (m, 1H), 3.90 (s, 3H), 3.77 (br s, 1H), 3.31 (dd, J = 3.3, 12.0 Hz, 1H), 2.93-2.84 (m, 3H), 1.78-1.54 (m, 4H), 1.49 (s, 9H); HRMS (ESI) [M+H]+ calcd for C29H34O5N5ClI 694.1288, found 694.1272; IR (ATR): 1714, 1675, 1591, 1513, 1434, 1405, 1311, 1280, 1243, 1222, 1172, 1110, 1060 cm-1; Anal. calcd for C29H33O5N5ClI: C, 50.19; H, 4.79; N, 10.09, found: C, 50.52; H, 4.95; N, 9.92.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-(Difluoromethoxy)aniline, and friends who are interested can also refer to it.

Reference:
Article; Ikuma, Yohei; Hochigai, Hitoshi; Kimura, Hidenori; Nunami, Noriko; Kobayashi, Tomonori; Uchiyama, Katsuya; Furuta, Yudai; Sakai, Mutsuko; Horiguchi, Masakuni; Masui, Yumi; Okazaki, Kazuhiko; Sato, Yasuhiro; Nakahira, Hiroyuki; Bioorganic and Medicinal Chemistry; vol. 20; 19; (2012); p. 5864 – 5883;,
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Adding a certain compound to certain chemical reactions, such as: 31576-51-9, name is 2-(2-Methoxyethoxy)ethanamine, 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 31576-51-9, Formula: C5H13NO2

General procedure: A solution of compound (ZDR019) (3.0 g, 7.88 mmol), dimethylamine hydrochloride (1.92 g, 23.6 mmol), sodium triacetoxyborohydride (3.32 g, 15.7 mmol) and N,N- diisopropylethylamine (4.8 ml_, 27.5 mmol) in 1,2-dichloroethane (150 mL) was stirred at room temperature for 18 h. The reaction was quenched through the addition of water (100 mL) and the pH adjusted to pH 6-7 using aqueous phosphate buffer solution (0.5 M, pH 7) . The mixture was then diluted with dichloromethane (100 mL) and the separated aqueous layer further extracted with dichloromethane (2 x 50 mL). The combined organic layers were washed with aqueous phosphate buffer solution (0.5 M, pH 7) (100 mL), dried over anhydrous magnesium sulfate, filtered and the filtrate concentrated in vacuo. Purification by flash chromatography (dichloromethane/methanol, 20: 1 10: 1 7: 1) afforded compound (ZDR022) as a white solid (2.40 g, 5.86 mmol, 74%).

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-Methoxyethoxy)ethanamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; OTAGO INNOVATION LIMITED; BRIMBLE, Margaret Anne; COOK, Greg Murray; FERGUSON, Scott Andrew; HEIKAL, Adam; RENNISON, David; (130 pag.)WO2019/125185; (2019); 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. 111-95-5, name is Bis(2-methoxyethyl)amine, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 111-95-5

Propargyl bromide (17.8 g, 150 mmol) was added dropwise to a mixture of bis(2-methoxyethyl)amine (20g, 150 mmol) and cesium carbonate (49 g, 150 mmol) in 350 mL of acetone. The mixture was stirred overnight under nitrogen at room temperature. The inorganic salts were then filtered off, and the solvent was removed. The residue was dissolved in saturated sodium bicarbonate solution and extracted with ethyl acetate. The organic extracts were then evaporated to give 20 g of bis-(2-methoxy-ethyl)-prop-2-ynyl-amine: mass spectrum (m/e): M+H 172.

According to the analysis of related databases, 111-95-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Wyeth Holdings Corporation; EP1171440; (2004); B1;,
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