Month: August 2021

Some common heterocyclic compound, 2393-23-9, name is 4-Methoxybenzylamine, molecular formula is C8H11NO, 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: 4-Methoxybenzylamine

1.1. Synthesis of bis-(4-methoxy-benzyl)-amine (Int. 1) p-Anisaldehyde (411 mmol), 4-methoxybenzylamine (411 mmol) and toluene (500 mL) were combined in a round bottomed flask fitted with a condenser and a Dean-Stark trap. The reaction was refluxed for 1 h during which water was removed from the reaction mixture. The reaction was cooled and concentrated. The residue was dissolved in MeOH (120 mL). The mixture was cooled to 5 C. and NaBH4 (205 mmol) was added in portions over 45 min. The reaction was slowly heated to reflux. After 2 h at reflux, the reaction was cooled to room temperature and concentrated. The residue was dissolved in EtOAc. The organic layer was washed (3*H2O and brine), dried (Na2SO4) and concentrated to yield the desired product.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2393-23-9, its application will become more common.

Reference:
Patent; MENET, Christel Jeanne Marie; MAMMOLITI, Oscar; BLANC, Javier; ORSULIC, Mislav; ROSCIC, Maja; US2015/203455; (2015); A1;,
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Reference of 349-65-5, These common heterocyclic compound, 349-65-5, name is 2-Methoxy-5-(trifluoromethyl)aniline, 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 solution of 2-methoxy-5-(trifluoromethyl)aniline (0.15 g) in anh CH2Cl2 (15 mL) at 0 C. was added CDl (0.13 g). The resulting solution was allowed to warm to room temp. over 1 h, was stirred at room temp. for 16 h, then was treated with 4-(2-(N-methylcarbamoyl)-4-pyridyloxy)aniline (0.18 g). The resulting yellow solution was stirred at room temp. for 72 h, then was treated with H2O (125 mL). The resulting aqueous mixture was extracted with EtOAc (2*150 mL). The combined organics were washed with a saturated NaCl solution (100 mL), dried (MgSO4) and concentrated under reduced pressure. The residue was triturated (90% EtOAc/10% hexane). The resulting white solids were collected by filtration and washed with EtOAc. The filtrate was concentrated under reduced pressure and the residual oil purified by column chromatography (gradient from 33% EtOAc/67% hexane to 50% EtOAc/50% hexane to 100% EtOAc) to give N-(2-methoxy-5-(trifluoromethyl)phenyl)-N’-(4-(2-(N-methylcarbamoyl)-4-pyridyloxy)phenyl) urea as a light tan solid (0.098 g, 30%): TLC (100% EtOAc) Rf 0.62; 1H NMR (DMSO-d6) delta 2.76 (d, J=4.8 Hz, 3H), 3.96 (s, 3H), 7.1-7.6 and 8.4-8.6 (m, 11H), 8.75 (d, J=4.8 Hz, 1H), 9.55 (s, 1H); FAB-MS m/z 461 ((M+H)+).

Statistics shows that 2-Methoxy-5-(trifluoromethyl)aniline is playing an increasingly important role. we look forward to future research findings about 349-65-5.

Reference:
Patent; Riedl, Bernd; Dumas, Jacques; Khire, Uday; Lowinger, Timothy B.; Scott, William J.; Smith, Roger A.; Wood, Jill E.; Monahan, Mary-Katherine; Natero, Reina; Renick, Joel; Sibley, Robert N.; US2001/11135; (2001); A1;,
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Synthetic Route of 651734-54-2, These common heterocyclic compound, 651734-54-2, name is 2,6-Difluoro-3,5-dimethoxyaniline, 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.

2,6-difluoro-3,5-dimethoxyaniline (27.0 g, 143 mmol) was added to 6.0 M hydrochloric acid solution (240 mL), and NaNO2 aqueous solution (10.35 g, 150 mmol, 30 mL water) was slowly added dropwise wider ice water for cooling within 25 min. After the addition was completed, the mixture was reacted for another 15 min to obtain an orange-re d suspension, and then added to an aqueous KI solution (94.9 g, 570 mmol, 150 mL water), the mixture was heated to room temperature and stirred for 30 min to precipitate a solid. The mixture was filtrated and washed with water to obtain a crude product. MeOH (60 mL) was added to the crude product, then the mixture was stirred at room temperature for 30 min, filtrated, and dried to obtain 2,4-difluoro-3-iodo-1,5-dimethoxybenzene (29.3 g, yield: 68%).

The synthetic route of 651734-54-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Abbisko Therapeutics Co., Ltd.; YANG, Fei; DENG, Haibing; YING, Haiyan; YU, Hongping; CHEN, Zhui; XU, Yaochang; (604 pag.)US2019/270742; (2019); A1;,
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Electric Literature of 4393-09-3,Some common heterocyclic compound, 4393-09-3, name is (2,3-Dimethoxyphenyl)methanamine, molecular formula is C9H13NO2, 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 74 The procedure described in Example 28 was repeated using N-(2,3-dimethoxybenzyl)-2-nitrobenzamide (obtained as a solid, m.p. 128-129 C., by reaction of 2-nitrobenzoyl chloride with 2,3-dimethoxybenzylamine) as starting material but with a reaction duration of 18 hours and using a mixture of ethanol and water (13/1 v/v) as the solvent. There was thus obtained 1,2-dihydro-2-(2,3-dimethoxybenzyl)-3H-indazol-3-one as a solid, m.p. 78-79 C. (recrystallized from aqueous ethanol), in 47% yield.

The synthetic route of 4393-09-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ICI Pharma; Imperial Chemical Industries PLC; US5173496; (1992); A;,
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Electric Literature of 29578-83-4, These common heterocyclic compound, 29578-83-4, name is 1-Bromo-3-methoxy-5-methylbenzene, 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 vigorously stirred mixture of 1 -Bromo-3-methoxy-5-methylbenzene (1 g, 4.97 mmol), Pyridine (3.22 mL, 39.8 mmol) and Water (8 ml) was added in small portions KMn04 (3.14g, 19.89 mmol) at 105C. The mixture which turned to a black suspension was stirred 24 hours at 105C, then cooled down to RT and filtered over Hyflo. The black residue was washed several times with EtOAc. The filtrate was then diluted in EtAOc and washed with a 2M solution of HCI. The organic layer was dried over sodium sulfate, filtered and concentrated to afford the title compound (281 mg, 24% yield) as a white solid. MS: 229.1 [M+H]+, Rt (1 ) = 1 .18 min.

Statistics shows that 1-Bromo-3-methoxy-5-methylbenzene is playing an increasingly important role. we look forward to future research findings about 29578-83-4.

Reference:
Patent; NOVARTIS AG; COOKE, Nigel Graham; FERNANDES GOMES DOS SANTOS, Paulo Antonio; FURET, Pascal; HEBACH, Christina; HOeGENAUER, Klemens; HOLLINGWORTH, Gregory; KALIS, Christoph; LEWIS, Ian; SMITH, Alexander Baxter; SOLDERMANN, Nicolas; STAUFFER, Frederic; STRANG, Ross; STOWASSER, Frank; TUFILLI, Nicola; VON MATT, Anette; WOLF, Romain; ZECRI, Frederic; WO2013/88404; (2013); A1;,
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Application of 20469-65-2,Some common heterocyclic compound, 20469-65-2, name is 1-Bromo-3,5-dimethoxybenzene, molecular formula is C8H9BrO2, 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 Pd-catalyzed cross-coupling reaction of 5-Bromo-l,3-dimethoxybenzene with allyl boronic acid pinacol ester produced 5-allyl~l,3-dimethoxybenzene 1 in excellent yield; Example 20 Synthesis of 5-AUyl-l,3-dimethoxybenzene5-Bromo-l,3-dimethoxybenzene (2.13 g, 9.8 mralphaol), CsF (2.88 g, 19.0 mmol), and Pd(Ph3)4 (0.57-1.13 g, 0.5-1.0 mmol) were weighed into a flame-dried Schlenk flask and put under a flow of argon. THF (80 mL) was added to the flask via syringe, and the resulting suspension was stirred for 30 min at room temperature. AHyI boronic acid pinacol ester (2.96 g, 17.6 mmol) in THF (40 ml) was added and the resulting mixture was heated to reflux for 30 h. Another portion of CsF (2.88 g, 19.0 mmol) and Pd(Ph3)4 (0.57-1.13 g, 0.5-1.0 mmol) were added and the reaction was continued to reflux for 24 h. The reaction mixture was diluted with petroleum ether (100 ml) followed by H2O (100 ml). The layers were separated and the aqueous layer was extracted with petroleum ether (2 x 80 ml). The combined organic layers were washed with H2O (100 ml), and brine (100 ml). The solution was dried over MgSO4 and evaporated to dryness. The crude product was purified by column chromatography (silica, eluent: hexanes/benzene = 3:2) to give 1.60 g (92%) of 5-Allyl-l,3- dimethoxybenzene. 1H NMR (CDCl3): delta 3.33 (d, J = 6.7 Hz, 2H, CH2CH=CH2), 3.77 (s, 6H, OCHi), 5.02-5.11 (m, 2H5. CH2CH=CH2), 5.89-5.99 (m, 1Eta, CH2CH=CH2), 6.33-6.38 (m, 3H).

The synthetic route of 20469-65-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE UNIVERSITY OF NORTH CAROLINA AT CHAPEL HILL; RUTERGS UNIVERSITY; WO2007/8847; (2007); A2;,
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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. 3616-56-6, name is 2,2-Diethoxy-N,N-dimethylethanamine, A new synthetic method of this compound is introduced below., SDS of cas: 3616-56-6

1) 1H, 1’H-2, 3′-twoversus(dimethylamino)Acetaldehyde acetalAccording to the molar ratio of 1:1 to 3,Stir in acetic acid for 6 hours.Rearrangement to obtain an intermediate with a yield of 91%

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; Wuhan Shang Sai Optoelectric Technology Co., Ltd.; Mu Guangyuan; Liu Feige; Zhuang Shaoqing; (28 pag.)CN109942581; (2019); A;,
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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. 16618-68-1, name is 3-Bromo-5-methoxyaniline, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 3-Bromo-5-methoxyaniline

To a solution of 5-bromo-3-(2-fluoropyridin-4-yl)-4-methyl-1-tosyl-1H-pyrrolo[2,3-b]pyridine from step 3 (258 mg, 0.56 mmol) in 1,4-dioxane (5 mL) was added potassium acetate (165 mg, 1.68 mmol), bis(pinacolato) diboron (569 mg, 2.24 mmol) and bis(diphenylphosphino)ferrocene]dichloropalladium(II).DCM (23 mg, 0.028 mmol). The solution was treated with microwave radiation at 130 C. for 3.5 hours. To this solution was added 3-bromo-5-methoxyaniline (113 mg, 0.56 mmol), potassium carbonate (232 mg, 1.68 mmol) and bis(diphenylphosphino)ferrocene]dichloropalladium(II).DCM (23 mg, 0.028 mmol). The solution was treated with microwave radiation at 120 C. for one hour. After cooling the resulting solution was partitioned between ethyl acetate and water. The organic layer was washed with water, brine and dried over magnesium sulfate. The mixture was filtered and concentrated in vacuo. The crude material was purified using normal phase chromatography (ethyl acetate/heptane) to provide 3-(3-(2-fluoropyridin-4-yl)-4-methyl-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-5-methoxyaniline (154 mg, 55% yield): MS (ES) m/z 503 (M+H).

According to the analysis of related databases, 16618-68-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Jacobsen, Eric Jon; Blinn, James Robert; Springer, John Robert; Hockerman, Susan L.; Anderson, David Randolph; (120 pag.)US2018/208594; (2018); A1;,
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Related Products of 17061-62-0, A common heterocyclic compound, 17061-62-0, name is Bis(4-methoxybenzyl)amine, molecular formula is C16H19NO2, 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 solution of bis(4-methoxybenzyl)amine 30.1 (900 g, 3.49 mol, 1 eq) in DCM (9 L) was added TEA (634 mL, 4.55 mol, 1.3 eq), followed by dropwise addition of ethanesulfonyl chloride (399 mL, 4.19 mol, 1.2 eq). (The internal temperature was kept between 5-10 C during the addition of the ethane sulfonyl chloride). Once the addition was complete, the cooling bath was removed. After 1.5 h, TLC showed complete loss of starting material. The reaction was quenched by the addition of water (4 L) to the reaction mixture. The layers were separated and the aqueous layer was extracted with DCM (2x 2 L). The combined organic layers were washed with brine (2x 1 L), dried over Na2SO4, and concentrated in vacuo. The material thus obtained was adsorbed onto a plug of silica gel and purified by chromatography (silica gel (60-120 mesh) eluting with a gradient of 10- 80% EtOAc in hexanes) to provide the title compound 30.0 (1125 g, 3.22 mol, 92%) as a white solid. 1H-NMR (400 MHz, CDCl3) delta 7.23 (dd, J = 2.08, 6.62 Hz, 4H), 6.90 (dd, J = 2.12, 6.60 Hz, 4H), 4.29 (s, 4H), 3.83 (m, 6H), 2.92 (q, J = 7.40 Hz, 2H), 1.33 (t, J = 7.40 Hz, 3H). GC-LCMS (ESI pos. ion) m/z: = 372.2 (M+Na)+.

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; AMGEN INC.; CHEN, Yinhong; CHENG, Alan C.; DEBENEDETTO, Mikkel V.; DRANSFIELD, Paul John; HARVEY, James S.; HOUZE, Jonathan; KHAKOO, Aarif Yusuf; LAI, Su-Jen; MA, Zhihua; PATTAROPONG, Vatee; SWAMINATH, Gayathri; KREIMAN, Charles; MOEBIUS, David C.; SHARMA, Ankit; (543 pag.)WO2018/93580; (2018); A1;,
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Related Products of 4179-19-5,Some common heterocyclic compound, 4179-19-5, name is 3,5-Dimethoxytoluene, 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.

A 3-necked round bottom flask was added 3,5-dimethoxytoluene (6.088g, 40mmol) and cyclohexane(28mL) under nitrogen.Was added dimethyl carbonate (30.3g,336mmol), at 60 deg.] Cand the reaction mixture was heated. After 15 minutes was added an excess of chlorosulfonic acid. By inserting the tubeof solid sodium hydroxide to remove HCl gas release. After the addition wascomplete, the reaction mixture was heated at 70-72 for one hour, then cooled toroom temperature. The solid was filtered off, washed with dimethyl carbonate /cyclohexane (1:1,20mL)and washed. The solid was dried under vacuum to give pure material (6.13g, 66%). To sulfonic acid (product fromthe above, 4.65g, 20mmol) and triethylamine(2.03g, 2.79mL) was added 2,4,6-trichloro-1,3,5triazine (cyanuric chloride, 3.69g, 20mmol)in (40 mL) in amixture of acetone-.The reaction mixture was heated at reflux for 20 hours, then cooled to room temperature. Thesolution was passed through a pad of Celite, and evaporated in vacuo to leave asolid, which was filtered off, washed with hexane. The product of cyanuric acidand hydroxides (cyanuric hydroxide) in a mixture of salt and triethylamine (was7.58 g) used in the next step without further purification. Fitted to acondenser (acetone – cooled with dry ice), 3-neck round bottom flask was addedthe mixture from step (was 7.58 g) and acetone (100mL). Thereaction mixture was cooled to -78 , ammonia gas intothe solution for 0.5hours. The reaction mixture was allowed to stand overnight, so that theammonia was slowlyevaporated, and then the solvent was evaporated. Water was added, the productwas extracted with DCM. The solvent was dried and evaporated to a mixture ofthe remaining solid and thick liquids. The solid was filtered off, washed withhexane, the remaining pure sulfonamide (3.23g,70%). To a round bottomflask was added 3,5-dimethyl-4-hydroxybenzoicacid (2.99g, 18mmol). Was added anhydrous DMF (20mL), and sodium hydride (1.8g, 45mmol). The reaction mixturewas stirred at roomtemperature for 1hour. Was added p-methoxybenzyl chloride (6.20g,39.6mmol), and the mixture was stirred at room temperature overnight (20 hours). Thereaction mixture was poured into water, acidified with 1N HCl and stirred for 1hour. The precipitated solid was filtered off, washed with water and hexane togive the pure B- cyclic structural unit (6.93g, 95%). The structural unitof the B- ring (6.93g, 17.1mmol) was dissolvedin a mixture of methanol(50mL) and tetrahydrofuran(50 mL) of. Waterwas added (20 mL) of potassium hydroxide (1.25g,22.2mmol). At 70 deg.] Cand the reaction mixture was refluxed for 24 hours. The solvent was evaporated in vacuo.Water was added, the reaction mixture was acidified with 1N HCl (pH4-5). Thesolid was filtered off, washed with water and hexanes. The yield was 4.61g (94%). Under nitrogen,above product (1.932g, 6.75mmol), and sulfonamidefrom above (1.04g, 4.5mmol) was added to a 3-neck round bottom flask. Dichloromethane was addedunder stirring (100mL). To this stirred mixture was addedN-(3-dimethylaminopropyl)-N’-ethylcarbodiimide hydrochloride (EDCI.HCl, 1.36g, 7.09mmol), followed by addition of N, N- dimethylaminopyridine(2.06g, 16.9mmol). At roomtemperature the reaction mixture was stirred for 24 hours, then washed with 1N HCI, 2.5%NaOH and saturated sodium bicarbonate solution. The organic layer was dried andevaporated in vacuo to leave a residue, which was purified by silica gel (100g)column chromatography using 20-50% hexane in ethyl acetate in methylenechloride and methanol as the eluting 5% purification agent. Fractions 30-66afforded pure material (1.35g, 60%). Under nitrogen,compounds from the previous step(0.105g, 0.21mmol) was dissolved in tetrahydrofuran, cooled to -78 . N-butyllithium was added, and the reaction mixture wasslowly warmed to roomtemperature and stirredovernight (~ 14 hours).TLC showed incomplete conversion. The reaction mixture was quenched withsaturated ammonium chloride solution, extracted with ethyl acetate. The solventwas evaporated in vacuo, the remaining residue, which was purified by silicagel (15g) column chromatography adopt in 20-50% ethyl acetate in hexanes aseluent. Product was not pure enough, thus making use of another pillar, the useof hexane in 0.5% methanol as eluent. Finally, the material was purified bypreparative TLC. Under nitrogen compounds from the previous step(0.277 g of) was dissolved in trifluoroacetic acid (10mL), and the reaction mixture was refluxed (bath temperature 80 ) 4 days. The solvent wasevaporated in vacuo, the residue was dissolvedin 0.25N NaOH (20mL), and acidified with acetic acid. At this time, the solidhas precipitated. The solid was filtered off, washed with water, washed withhexane, and dried. 0.005g of pure substances isolated from the batch. 0.060gcompound isolated from another batch, which is not enough pure. The compoundwas further purified by preparative HPLC, to give pure 6,8-dimethoxy-3-(4-hydroxy-3,5-dimethylphenyl) -2H-1,2- benzothiazine 1,1-…

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3,5-Dimethoxytoluene, its application will become more common.

Reference:
Patent; RESVERLOGIX CORP; HANSEN, H; (62 pag.)CN103319408; (2016); B;,
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