Month: June 2021

Adding a certain compound to certain chemical reactions, such as: 54314-84-0, name is ((3-Bromopropoxy)methyl)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 54314-84-0, category: ethers-buliding-blocks

Reference Example 9[4-(3-Benzyloxypropoxy)-2-methylphenyl]methanol To a solution of 4-bromo-3-methylphenol (2.5 g) inN,N-dimethylformamide (10 mL) were added cesium carbonate (4.79 g), benzyl 3-bromopropyl ether (2.48 mL) and a catalytic amount of sodium iodide, and the mixture was stirred at room temperature for 60 hours. The reaction mixture was poured into water, and the resulting mixture was extracted with diethyl ether. The organic layer was washed with water, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to give 4-(3-benzyloxypropoxy)-1-bromo-2-methylbenzene. This material was dissolved in tetrahydrofuran (100 mL). To the solution was added n-butyl lithium (2.46 mol/Ln-hexane solution, 6 mL) at -78°C under an argon atmosphere, and the mixture was stirred for 5 minutes. To the reaction mixture was added N,N-dimethylformamide (2.57 mL), and the mixture was allowed to warm to 0°C and stirred for 1 hour. The reaction mixture was poured into water, and the resulting mixture was extracted with diethyl ether. The organic layer was washed with water and brine successively, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to give 4-(3-benzyloxypropoxy)-2-methylbenzaldehyde. This material was dissolved in ethanol (40 mL). To the solution was added sodium borohydride (506 mg), and the mixture was stirred at room temperature overnight. To the reaction mixture was added methanol, and the resulting mixture was concentrated under reduced pressure. Water was added to the residue, and the mixture was extracted with diethyl ether. The organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate = 5/1 – 1.5/1) to give the title compound (3.33 g).1HNMR (CDCl3) delta ppm: 1. 37 (1H, t, J=5.7Hz), 2.0-2.15 (2H, m), 2.36 (3H, s), 3. 66 (2H, t, J=6.2Hz), 4.08 (2H, t, J=6.3Hz), 4.52 (2H, s), 4.63 (2H, d, J=5.7Hz), 6.65-6.8 (2H, m), 7.15-7.4 (6H, m)

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; Kissei Pharmaceutical Co., Ltd.; EP1548024; (2005); A1;,
Ether – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 89282-70-2, name is 2-Methoxy-2-methylpropan-1-amine, 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 89282-70-2, Recommanded Product: 89282-70-2

A mixture of phenyl 5-({trans-4-[(2-chloro-4-fluorophenyl)carbamoyl]cyclohexyl}carbamoyl)-1 H-imidazole-4-carboxylate (150 mg, 0.309 mmol,) and 2-methoxy-2-methylpropan-1 -amine(160 mg, 1.55 mmol, GAS No 89282-70-2) in tetrahydrofuran (4.8 ml) was stirred at 600over night. For work-up, the reaction mixture was concentrated and the residue was purified by flash chromatography (25 g Snap Cartridge, ethyl acetate/ethanol gradient, 0% -> 5% ethanol) to yield the title compound (18.0 mg, 12 yield).[C-MS (Method 6): R = 1 .08 mm; MS (ESIpos) m/z = 494.2 [M+H].1HNMR (400 MHz, DMSO-d6): 6 [ppm] = 13.20-12.45 (m, 1H), 11.43-1 0.70 (m, 1H), 9.52 (s,1H), 8.69-7.89 (m, 1H), 7.82 (s, 1H), 7.65-7.57 (m, 1H), 7.53-7.47 (m, 1H), 7.27-7.18 (m,1H), 3.89-3.66 (m, 1H), 3.37 (d, 2H), 3.15 (s, 3H), 2.48-2.38 (m, 1H), 2.10-1.75 (m, 4H),1.71 -1 .32 (m, 4H), 1.14 (s, 6H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Methoxy-2-methylpropan-1-amine, and friends who are interested can also refer to it.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; EIS, Knut; ACKERMANN, Jens; WAGNER, Sarah; BUCHGRABER, Philipp; SUeLZLE, Detlev; HOLTON, Simon; BENDER, Eckhard; LI, Volkhart; LIU, Ningshu; SIEGEL, Franziska; LIENAU, Philip; BAIRLEIN, Michaela; VON NUSSBAUM, Franz; HERBERT,Simon; KOPPITZ, Marcus; (734 pag.)WO2016/177658; (2016); A1;,
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Synthetic Route of 54314-84-0, A common heterocyclic compound, 54314-84-0, name is ((3-Bromopropoxy)methyl)benzene, molecular formula is C10H13BrO, 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: methyl 2-cyanoacetate (23 g, 232 mmol) was addeddropwise to a suspension of sodium hydride (60percent, 2.79 g,69.7 mmol) in DMF (100 mL) and THF (100 mL) at 0 C, and thereaction mixture was warmed to rt and stirred at rt for 30 min.((2-Bromoethoxy)methyl)benzene (10 g, 46.5 mmol) was added,and the reaction mixture was stirred at rt for 12 h. Water wasadded and the aqueous layer was extracted with ether (3). Thecombined organic layers were washed with brine, dried over anhydroussodium sulfate, and filtered, and the filtrate was evaporatedto give the crude product. Excessive methyl 2-cyanoacetate wasremoved by distillation under high vacuum at 120?130 C, andremaining residue was purified by silica gel chromatography elutingwith 0?50percent EtOAc/hexanes to give methyl 4-(benzyloxy)-2-cyanobutanoate (8 g, 74percent) as a colorless liquid. 1H NMR(300 MHz, CDCl3) d 7.3 (m, 5H), 4.51 (s, 2H), 3.70 (s, 3H), 3.6?3.9(m, 3H), and 2.3 (m, 2H). LC/MS m/z: (M+H)+ calcd forC13H16NO3, 234.11; found 234.4. Step B: To a suspension of sodiumhydride (60percent, 9 g, 225 mmol) in THF (170 mL) and DMF (170 mL)was added methyl 4-(benzyloxy)-2-cyanobutanoate (35 g,150 mmol) at 0 C, and the reaction mixture was stirred at rt for30 min. ((3-Bromopropoxy)methyl)benzene (37.8 g, 165 mmol)was added, and the reaction mixture was stirred at rt for 12 h.Water was added and the aqueous layer was extracted with ether(3). The combined organic layers were washed with brine, driedover anhydrous sodium sulfate, and filtered, and the filtrate wasevaporated to give the crude product. The crude product was purifiedby silica gel chromatography eluting with 0?40percent EtOAc/hexanesto give 22 (40 g, 70percent) as a colorless oil. 1H NMR (400 MHz,CDCl3) d 7.3 (m, 10H), 4.48 (2H, s), 4.47 (2H, s), 3.7 (m, 2H), 3.57(3H, s), 3.48 (m, 1H), 2.42 (m, 1H), 1.8?2.1 (m, 4H), and 1.6 (m,1H). LC/MS m/z: (M+H)+ calcd for C23H28NO4, 382.20; found 382.4.

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; Wu, Yong-Jin; Guernon, Jason; McClure, Andrea; Luo, Guanglin; Rajamani, Ramkumar; Ng, Alicia; Easton, Amy; Newton, Amy; Bourin, Clotilde; Parker, Dawn; Mosure, Kathleen; Barnaby, Omar; Soars, Matthew G.; Knox, Ronald J.; Matchett, Michele; Pieschl, Rick; Herrington, James; Chen, Ping; Sivarao; Bristow, Linda J.; Meanwell, Nicholas A.; Bronson, Joanne; Olson, Richard; Thompson, Lorin A.; Dzierba, Carolyn; Bioorganic and Medicinal Chemistry; vol. 25; 20; (2017); p. 5490 – 5505;,
Ether – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 6851-80-5, name is 1-(2-Methoxyphenyl)-N-methylmethanamine, 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 6851-80-5, Application In Synthesis of 1-(2-Methoxyphenyl)-N-methylmethanamine

General procedure FStep 1 / synthesis of substituted N-benzyl-4-chloro-N-methylbutanamide : Triethylamine (1 eq) and 4-chlorobutyryl chloride (1 eq) were added to a solution of the substituted N-methylbenzylamine (1 eq) in dichloromethane (1.3 ml_/ mmol). The mixture was stirred 3 hours at room temperature then water was added. The resulting mixture was extracted 3 times with dichloromethane, the combined organic layers were dried with anhydrous MgSO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography (silica gel) with the appropriate gradient determined by TLC to give the substituted N-benzyl-4-chloro-N-methylbutanamide. Step 2 / alkylation of thiols with substituted N-benzyl-4-chloro-N-methylbutanamide: Anhydrous potassium carbonate (1.5eq) and substituted N-benzyl-4-chloro-N- methylbutanamide (1 eq) were added to a solution of the thiol derivative (1 eq) in acetonitrile (6 mL / mmol). The mixture was refluxed overnight then water and ethyl acetate was added after cooling. The mixture was extracted 3 times with ethyl acetate, the combined organic layers were washed with brine, dried with anhydrous MgSO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography (silica gel) with the appropriate gradient determined by TLC to give the thio-ether.The following compounds were prepared according general procedure F :Example 138 : 4-[(3,4-Difluorophenyl)thio]-N-(2-methoxybenzyl)-N-methylbutanamidePrepared from commercial 3,4-difluorothiophenol and commercial 2-methoxy-N- methylbenzylamine in 27% yield.NMR-1H (CDCI3) : delta (ppm) 7.32-6.85 (m, 7H) ; 4.55 (d, 2H) ; 3.84-3.82 (m, 3H) ; 3.03-2.92(m, 5H) ; 2.50 (t, 2H) ; 2.04-1 .94 (m, 2H) MS (ESI+) : m/z = 366 [M+H]+

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, 1-(2-Methoxyphenyl)-N-methylmethanamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CELLVIR; INSTITUT NATIONAL DE LA SANTE ET DE LA RECHERCHE MEDICALE (INSERM); CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE (C.N.R.S); BENAROUS, Richard; BARBEY-TREVE, Sabine; PARIS, Jean-Marc; BERRUT, Sebastien; BERLIOZ-TORRENT, Clarisse; EMILIANI, Stephane; WO2010/66847; (2010); A1;,
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Synthetic Route of 538-86-3, 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 538-86-3 as follows.

General procedure: A mixture of nitriles (5 mmol), methyl ethers (6 mmol) and Fe(ClO4)3·H2O (5percentmol) was placed in a round bottom flask. Then the reaction mixture was heated at 100 °C for the given time. After completion of the reaction monitored by thin layer chromatography (TLC), 10 ml water was added into reaction system and extracted with ethyl acetate (3 × 20 ml). The organic layers were collected, combined, washed with water (3 × 20 ml), dried over anhydrous Na2SO4, and concentrated under vacuum. The pure products (1a?1k and 2a?2p) were obtained by directly passing through a silica gel (200?300 mesh) column using petroleum ether/ethyl acetate (10:1?5:1).

According to the analysis of related databases, 538-86-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Yin, Guibo; Yan, Bin; Chen, Junqing; Ji, Min; Journal of the Iranian Chemical Society; vol. 16; 6; (2019); p. 1355 – 1363;,
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Application 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.

EXAMPLE 2; Preparation of 2-chloro-N-[(lS)-1-(4-methoxyphenyl) ethyl] -6-methyl-4-propoxy-3-pyridine- carboxamide (Compound 103); To 2-chloro-6-methyl-4-propoxy-3-pyridinecarboxylic acid (i. e. product of Example 1, Step A) (100 mg) was added thionyl chloride (2 mL), and the reaction mixture was stirred at room temperature for 2 hours. The excess thionyl chloride was evaporated in vacuo, and dichloromethane was added and evaporated in vacuo. The residual oil was dissolved in dichloromethane (approximately 2 mL) and added to a solution of (aS)-4-methoxy- a-methylbenzenemethanamine (79.2 mg) in dichloromethane (3 mL). A molar excess of PS-DMAP was added, and the reaction mixture was shaken at room temperature overnight. The reaction mixture was then filtered, and the solvent was evaporated in vacuo. The residual oil was triturated with 1-chlorobutane-hexanes (approximately 1: 1) to provide the title product, a compound of the present invention, as a white solid (92.3 mg) melting at 110-111 C. 1H NMR (CDC13,300 MHz) 8 7.33 (d, 2H), 6. 87 (d, 2H), 6.61 (s, 1H), 5.88 (br d, 1H), 5.29-5. 39 (m, 1H), 3.96 (t, 2H), 3.80 (s, 3H), 2.48 (s, 3H), 1.73-1. 84 (m, 2H), 1.59 (d, 3H), 0.98 (t, 3H)

The synthetic route of 6298-96-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; E.I. DUPONT DE NEMOURS AND COMPANY; WO2005/70889; (2005); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Adding a certain compound to certain chemical reactions, such as: 5111-65-9, name is 2-Bromo-6-methoxynaphthalene, 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 5111-65-9, Computed Properties of C11H9BrO

6-Methoxy-2-naphthaldehyde ((a) Harvey, R. G.; Cortez, C.; Sawyer, T. W.; DiGiovanni, J.; J. Med. Chem. 1988, 31, 1308-1312. (b) Harvey, R. G.; Cortez, C. Tetrahedron, 1997, 53, 7101-7118) was prepared by formylation (Beringer, F. M.; Nathan, R. A. J. Org. Chem. 1969, 34, 685-689) of 6-methoxy-2-bromonaphthalene in 53% yield.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Bromo-6-methoxynaphthalene, and friends who are interested can also refer to it.

Reference:
Patent; University of Pittsburgh; US6706839; (2004); B1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Reference of 93919-56-3,Some common heterocyclic compound, 93919-56-3, name is (4-(Trifluoromethoxy)phenyl)methanamine, molecular formula is C8H8F3NO, 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.

EXAMPLE 81 N-1H-indol-4-yl-N’-[4-(trifluoromethoxy)benzyl]urea 4-(Trifluoromethoxy)benzylamine (0.21g, 1.1 mmol) and the product of Example 80A (0.16 g, 1 mmol) were treated as described in Example 80B to provide the title compound (0.23 g). mp 177 C.; 1H NMR (300 MHz, DMSO-d6) delta 4.36 (d, 2 H), 6.52 (m, 1H), 6.95 (m, 3H), 7.24 (t, 1 H), 7.36 (d, 2H), 7.48 (d, 2H), 7. 63 (dd, 1H), 8.32 (1H), 11.06 (s, 1H); MS (DCI+) m/z 349.9 (M+H)+; Anal. Calcd. For C17H14N3F3O2: C, 58.63, H. 4.34, N, 12.07. Found: C, 58.51, H, 3.98, N, 12.03.

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

Reference:
Patent; Lee, Chih-Hung; Bayburt, Erol K.; DiDomenico JR., Stanley; Drizin, Irene; Gomtsyan, Arthur R.; Koenig, John R.; Perner, Richard J.; Schmidt JR., Robert G.; Turner, Sean C.; White, Tammie K.; Zheng, Guo Zhu; US2003/158188; (2003); A1;,
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Some common heterocyclic compound, 4698-11-7, name is 10-Methoxy-5H-dibenzo[b,f]azepine, molecular formula is C15H13NO, 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. Recommanded Product: 10-Methoxy-5H-dibenzo[b,f]azepine

EXAMPLE I; Preparation of 5,11-Dihydro-10H-dibenz[b,f]azepine-10-one (Oximinostilbene) IV; A 2-L, three-necked flask equipped with a mechanical stirrer, thermometer and nitrogen inlet was charged with 10-methoxyiminostilbene I (110.0 g, 0.49 mol) and 330 mL acetone. A 10% solution of hydrochloric acid (28.6 g, 0.08 mol) was then added. The reaction mixture was stirred at ambient temperature for 1-1.5 hours until reaction completion. The product was precipitated by the addition of 660 mL of deionized water, and the resulting suspension was stirred for 3-4 hours. The suspension was filtered and washed with water. After drying, oximinostilbene (99.92 g, 97%) was obtained as a bright yellow solid having a purity of 99% by HPLC. 1H NMR (CDCl3, d): 3.80, 6.87, 7.04-7.15, 7.22-7.24, 7.32-7.37, 8.04 ppm.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4698-11-7, its application will become more common.

Reference:
Patent; Apotex Pharmachem Inc.; US2005/282797; (2005); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Related Products of 7252-83-7,Some common heterocyclic compound, 7252-83-7, name is 2-Bromo-1,1-dimethoxyethane, molecular formula is C4H9BrO2, 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 6-chloro-1,2- diazinan-3-amine (10 g, 73.75 mmol, l.OOequiv), 2-bromo-l,l-dimethoxyethane (50 g, 295.83 mmol, 4.01 equiv), and HBr(40%, 45 mL) in ethanol (100 mL) was stirred overnight at 90 C. The majority of the ethanol was removed under reduced pressure then the pH value of the solution was adjusted to 10 with 5% aqueous potassium carbonate solution. The resulting mixture was extracted with 6×500 mL of ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was purified on a silica gel column eluted with ethyl acetate/petroleum ether (1 /2-1 /1) to give 6,5 g (57%) of the title compound as a yellow solid. NMR (300 MHz, CDCl3 ) delta 7.95 (s, 1 H), 7.91 (s, 1 H), 7.80 (s, 1 H), 7.05 (d,.7 = 9.3 Hz, 1 H).

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-1,1-dimethoxyethane, its application will become more common.

Reference:
Patent; GENENTECH, INC.; FORMA TM, LLC; BAIR, Kenneth W.; BAUMEISTER, Timm R.; DRAGOVICH, Peter; GOSSELIN, Francis; YUEN, Po-Wai; ZAK, Mark; ZHENG, Xiaozhang; WO2013/127267; (2013); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem