Month: June 2021

Electric Literature of 13468-02-5,Some common heterocyclic compound, 13468-02-5, name is N,N-Dimethyl-2-phenoxyethanamine, molecular formula is C10H15NO, 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.

The oil XI 132g (0.8mol), 30% concentrated hydrochloric acid 195g (1.6mol) was dissolved in 400ml of water with stirring, at -10 temperature or less, 40% formaldehyde was slowly added dropwise a solution of 40g (0.8mol) reaction was continued for 2 hours; TLC monitoring completion of the reaction, the pH was adjusted to 8 with sodium carbonate to 9, and extracted twice with dichloromethane, organic phases were combined and concentrated to give an oil, 300ml ethyl acetate was added to dissolve,Was added dropwise 30% HCl / ethanol, precipitated crystals were filtered to give 112.7g compound XII, a yield of 56.3%;

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

Reference:
Patent; Weihai Di Su Pharmaceutical Co., Ltd.; Wu, Ronggui; Jiang, Kai; An, Donghua; Cui, Yangyang; Men, Lianbin; (7 pag.)CN105985257; (2016); A;,
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Synthetic Route of 6298-96-0, A common heterocyclic compound, 6298-96-0, name is 1-(4-Methoxyphenyl)ethylamine, molecular formula is C9H13NO, 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.

To a 250 mL RBF was added (S)-1-(4-methoxyphenyl)ethanamine (6.24 ml, 42.3 mmol), 1-(5- methylpyridin-2-yl)ethanone (6.0 g, 44.4 mmol), DCM (Volume: 106 ml) and STAB-H (17.92 g, 85 mmol) at rt and the reaction was stirred for 24h. The reaction was quenched by the addition of 1N NaOH until a pH of 8 was achieved. The phases were separated and the organic layer was treated with 1N NaOH until pH 11 was observed. The DCM layer was dried with MgSO4, filtered and concentrated to an oily residue. The residue was purified via combiflash to separate the diastereomers (~4:1 by crude NMR, 80g column 10-30% EtOAc in hexanes, over 40 min). The fractions were concentrated to a clear oil which was crystallized using hexanes (S)-1-(4-methoxyphenyl)-N-((S)-1-(5-methylpyridin-2-yl)ethyl)ethanamine (5.1 g, 18.86 mmol, 45 % yield). 1H NMR (400 MHz, CDCl3): delta= 8.40 (d, J= 2.1 Hz, 1H), 7.39 (ddd, J= 7.8, 2.4, 0.8 Hz, 1H), 7.15 (d, J= 8.5 Hz, 2H), 6.93 (d, J= 8.1 Hz, 1H), 6.83 (d, J= 8.5 Hz, 2H), 3.78 (s, 3H), 3.53 (q, J= 6.8 Hz, 1H), 3.37 (q, J= 6.6 Hz, 1H), 1.26 (d, J= 6.4 Hz, 3H), 1.24 (d, J= 6.5 Hz, 3H); LC/MS 75% MeOH in H2O over 3 minutes, rt = 0.480 at 254 nM, MS (+) 271.2.

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; EMORY UNIVERSITY; LIOTTA, Dennis C.; JECS, Edgars; WILSON, Robert James; NGUYEN, Huy Hoang; KIM, Michelle Bora; WILSON, Lawrence; MILLER, Eric James; TAHIROVIC, Yesim Altas; TRUAX, Valarie; KAISER, Thomas; (311 pag.)WO2018/156595; (2018); A1;,
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Reference of 2752-17-2, These common heterocyclic compound, 2752-17-2, name is 2,2′-Oxydiethanamine, 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.

o-Vanillin (1.82 g, 12 mmol) in EtOH (5 mL) was added dropwise to a 5 mL EtOH solution of3-oxapentane-1,5-diamine (0.52 g, 5 mmol). After the completion of addition, the solutionwas stirred for an additional 4 h at 78C. After cooling to room temperature, the precipitatewas filtered off. The product was dried in vacuo and obtained as a yellow crystalline solid.Yield: 1.59 g (68.0%). Anal. C20H24O5N2: Calcd C, 64.50; H, 6.50; N, 7.52%; found: C, 64.30; H,6.51; N, 7.51%. Selected IR data (KBr, nu/cm-1), 1629(nuC=N), 1256(nuC-O-C), 1047(nuOH). UV-vis(DMF): lambda = 271, 330 nm. Lambdam (DMF, 297 K): 1.7 S cm2 mol-1.

The synthetic route of 2752-17-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Shi, Xinkui; Mao, Shanshan; Shen, Kesheng; Wu, Huilu; Tang, Xia; Journal of Coordination Chemistry; vol. 70; 12; (2017); p. 2015 – 2028;,
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Adding a certain compound to certain chemical reactions, such as: 20781-20-8, name is (2,4-Dimethoxyphenyl)methanamine, 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 20781-20-8, SDS of cas: 20781-20-8

To a solution of 2-methyl-5-nitrobenzoic acid (1.0 g, 5.52 mmol) in methanol (10 mL) was added cone. H2S04 (0.5 mL) and the reaction mixture was heated at reflux for 16 h. Then the reaction mixture was concentrated and the residue was diluted with EtOAc. Then the mixture was washed with saturated aqueous NaHC03 solution, water and brine. The organic layer was separated, dried, filtered and concentrated to afford 1.0 g of methyl 2-methyl-5-nitrobenzoate which was used for the next step without further purification. A mixture of methyl 2-methyl-5-nitrobenzoate (1.0 g, 5.12 mmol) and l-ie/t-butoxy- N,N,N’,N’-tetramethylmethanediamine (2.23 g, 12.81 mmol) was heated at 1 15 C for 2 h. Then the reaction mixtuer was concentrated and purified by column chromatography to afford 600 mg of (E)-methyl 2-(2-(dimethylamino)vinyl)-5- nitrobenzoate. To a solution of (E)-methyl 2-(2-(dimethylamino)vinyl)-5- nitrobenzoate (600 mg, 2.40 mmol) in toluene (5 mL) was added (2,4- dimethoxyphenyl)methanamine (602 mg, 3.60 mmol) and the reaction mixture was heated at 120 C for 2 h. Then the reaction mixture was concentrated and the residue was triturated with EtOAc: Et20 (1 :9) and the solid precipitate was filtered and dried to afford 700 mg of the title product. 1H NMR (400 MHz, DMSO- 6): delta 9.32-9.31 (d, = 2.4 Hz, 1H), 8.41-8.38 (dd, = 2.4, 8.8 Hz, 1H), 7.62-7.60 (d, = 9.6 Hz, 1H), 7.48-7.46 (d, J = 7.2 Hz, 1H), 7.44-7.42 (d, J = 8.0 Hz, 1H), 6.52-6.49 (m, 3H), 5.15 (s, 2H), 3.86 (s, 3H), 3.82 (s, 3H).

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, (2,4-Dimethoxyphenyl)methanamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GLENMARK PHARMACEUTICALS S.A.; GHARAT, Laxmikant Atmaram; BANERJEE, Abhisek; KHAIRATKAR-JOSHI, Neelima; KATTIGE, Vidya Ganapati; WO2014/167444; (2014); A1;,
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Reference of 707-07-3, 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. 707-07-3, name is (Trimethoxymethyl)benzene, This compound has unique chemical properties. The synthetic route is as follows.

4-(2-Azidoethyl)phenyl 4-0-benzoyl-2,6-di-0-benzyl-p-D-galactopyranoside (16)To a solution of 15 (1 .17 g, 2.31 mmol) in toluene (15 mL) were added trimethylortho- benzoate (0.64 mL, 3.72 mmol) and p-TsOH (1 18 mg, 0.62 mmol). The mixture was stirred at 45C overnight, then concentrated and the residue dissolved in 90% aq AcOH (15 mL). The solution was stirred for 2 h at 60C, concentrated, and the residue was purified by flash chromatography (petroleum ether/EtOAc, 9:1 to 7:3) to yield 16 (1 .30 g, 2.14 mmol, 93%) as a colorless oil. (0231) [a]D20 -8.4 (c 1.00, CHCI3); 1H NMR (500 MHz, CDCI3): delta 2.83 (t, J = 7.3 Hz, 2H, (0232) CH2CH2N3), 3.44 (t, J = 7.3 Hz, 2H, CH2CH2N3) 3.60-3.66 (m, 2H, H-6), 3.87 (dd, J = 7.4, (0233) 9.6 Hz, 1 H, H-2), 3.92 (dd, J = 3.5, 9.6 Hz, 1 H, H-3), 3.96 (t, J = 6.2 Hz, 1 H, H-5), 4.41 , 4.48 (A, B of AB, J = 1 1 .7 Hz, 2H, CH2Ph), 4.78 (A of AB, J = 1 1 .2 Hz, 1 H, CH2Ph), 4.99- (0234) 5.07 (m, 2H, H-1 , CH2Ph), 5.63 (d, J = 2.8 Hz, 1 H, H-4), 7.06, 7.12 (AA, BB’ of AA’BB’, J = 8.5 Hz, 4H, C6H4), 7.18-7.35 (m, 10H, 2 C6H5), 7.43 (t, J = 7.8 Hz, 2H, C6H5), 7.56 (t, J = 7.4 Hz, 1 H, C6H5), 8.04-8.09 (m, 2H, C6H5); 13C NMR (126 MHz, CDCI3): delta 34.62 (0235) (CH2CH2N3), 52.63 (CH2CH2N3), 68.61 (C-6), 70.25 (C-4), 72.21 (C-3), 73.28 (C-5), 73.71 , 75.13 (2 CH2Ph), 79.15 (C-2), 101 .89 (C-1 ), 1 17.07 (2C, C6H4), 127.76, 127.78, 128.04, 128.29, 128.39, 128.49, 128.58, 129.57 (12C, 3 C6H5), 129.93 (2C, C6H4), 130.10, 132.46, 133.38, 137.79 (6C, 3 C6H5), 138.06, 156.17 (C6H4), 166.38 (CO); ESI-MS: m/z: calcd for C35H35N3Na07 [M+Na]+: 532.24, found: 532.28; IR (film): 2102 cm”1 (N3).

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

Reference:
Patent; UNIVERSITAET BASEL; ERNST, Beat; HERRENDORFF, Ruben; STECK, Andreas; YANG, Fan; WO2015/136027; (2015); A1;,
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Synthetic Route of 634-36-6, A common heterocyclic compound, 634-36-6, name is 1,2,3-Trimethoxybenzene, molecular formula is C9H12O3, 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.

General procedure: A pyrex test tube containing solid of 1,3,5-trimethoxybenzene (1a, 0.3 mmol), carbon tetrabromide (0.075 mmol), AQN-2-CO2H (0.03 mmol) and dry EtOH (5 mL) was irradiated for 20 h at roomtemperature with stirring by a 21W fluorescent lamp under air. The reactionmixture was concentrated in vacuo, quenched with aq Na2S2O3 and extractedwith EtOAc. The organic layer was dried over MgSO4 and concentrated invacuo. Purification of the residue by flash chromatography on silica gel(hexane/ethyl acetate = 6:1) provided 2-bromo-1,3,5-trimethoxybenzene (2a)(66.8 mg, 90%,) as a white solid.

The synthetic route of 634-36-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Tanaka, Masanori; Kamito, Yuji; Lei, Cui; Tada, Norihiro; Itoh, Akichika; Tetrahedron Letters; vol. 56; 43; (2015); p. 5886 – 5888;,
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18800-30-1, name is 1-Bromo-4-(2-bromoethoxy)benzene, belongs to ethers-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Computed Properties of C8H8Br2O

l-Bromo-4-(2-bromoethoxy)benzene (95 mg, 0.34 mmol) was added to a mixture of N-[2-(3-azetidinyloxy)-5,6-dichloro-3-pyridinyl]-2-chloro-4-pyridinecarboxamide (i.e. the product of Step C) (100 mg, 0.28 mmol) and N,N-diisopropylethylamine (76 mL, 0.42 mmol) in acetonitrile (3 mL), and the reaction mixture was heated at 60 C overnight. The cooled solution was treated with saturated aqueous sodium bicarbonate solution (2 mL) and water (2 mL), and then diluted with dichloromethane before being filtered through a tube containing Celite diatomaceous filter aid, eluting with dichloromethane. The residue after concentration was purified by chromatography (silica gel, ethyl acetate to 5% methanol in ethyl acetate) to give the title product, a compound of the present invention, as a pale yellow oil (84 mg)..H NMR delta 8.88 (s, 1H), 8.62 (d, 1H), 8.28 (br s, 1H), 7.77 (d, 1H), 7.62 (d, 1H), 7.37 (d, 2H), 6.78 (d, 2H), 5.35 (m, 1H), 3.99 (t, 2H), 3.92 (t, 2H), 3.42 (br s, 2H), 2.95 (t, 2H).

The synthetic route of 18800-30-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; E. I. DU PONT DE NEMOURS AND COMPANY; CLARK, David Alan; LAHM, George, P.; WO2012/12366; (2012); A1;,
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Reference of 1515-81-7,Some common heterocyclic compound, 1515-81-7, name is 1-Methoxy-4-(methoxymethyl)benzene, molecular formula is C9H12O2, 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: Toan oven-dried round-bottomed flask under N2 atmosphere was added CH2Cl2(5 mL), thiol (1.0 mmol), p-methoxybenzylmethyl ether (167 mL,167 mg, 1.10 mmol), TMSOTf (271 muL, 333 mg, 1.50 mmol), anddiisopropylethylamine (244 muL, 181 mg, 1.40 mmol). The homogenous mixture was stirredovernight and then passed through a column of silica (2 cm x 1 cm) with Et2O.The solvent was removed in vacuo and the residue was purified by columnchromatography (0-2% EtOAc/hexanes).

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

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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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. 37466-89-0, name is 3-Methoxybenzene-1,2-diamine, This compound has unique chemical properties. The synthetic route is as follows., Formula: C7H10N2O

To a solution of 1.35 g of tert.-butoxycarbonyl-methylamino-propanoic acid in 5OmL DCM were added 3.4 mL of DIPEA, 81 mg of DMAP, 1.0 g of HOBt, 1.5 g of EDC and 0.91 g of 3-methoxybenzene-1 ,2-diamine. The resulting mixture was stirred at rt for 3 h and then quenched with water. The organic phase was washed with sat. aq. NaHCO3, dried over MgSO4 and concentrated on vacuo to yield 2.9 g of [2-(2-amino-3-methoxy- phenylcarbamoyl)-ethyl]-methyl-carbamic acid tert. -butyl ester as brown oil. LC-MS: tR = 0.72 min; [M+H]+: 324.35.

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 37466-89-0.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; WO2008/132679; (2008); 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. 1515-81-7, name is 1-Methoxy-4-(methoxymethyl)benzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. COA of Formula: C9H12O2

General procedure: To a solution of alkoxybenzylalcohol 1 (0.2 mmol) in CF3CH2OH (1 mL) were added LiBr·H2O (0.2 mmol) and PhI(OAc)2 (0.2 mmol) atroom temperature. After completion of the reaction as indicated by TLC monitoring, saturated aq. Na2SO3 wasadded and the mixture was extracted with CH2Cl2. The combined organic layers were washed with brine, driedover anhydrous Na2SO4 and then concentrated in vacuo. The residue was purified by silica gel columnchromatography to afford pure monobrominated compounds 2.

The synthetic route of 1515-81-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Shibata, Ayako; Kitamoto, Sara; Fujimura, Kazuma; Hirose, Yuuka; Hamamoto, Hiromi; Nakamura, Akira; Miki, Yasuyoshi; Maegawa, Tomohiro; Synlett; vol. 29; 17; (2018); p. 2275 – 2278;,
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