Month: August 2021

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. 701-56-4, name is 4-Methoxy-N,N-dimethylaniline, A new synthetic method of this compound is introduced below., Recommanded Product: 701-56-4

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 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; Huang, Pei; He, Bang-Yue; Wang, Hui-Min; Lu, Jian-Mei; Synthesis; vol. 47; 2; (2015); p. 221 – 227;,
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Synthetic Route of 111-95-5, These common heterocyclic compound, 111-95-5, name is Bis(2-methoxyethyl)amine, 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.

The [6-[(4-chlorophenylsulfonyl)(2,5-difluorophenyl)methyl]pyridin-3-yl]carbaldehyde (100 mg, 0.245 mmol) obtained in Example 47, bis(2-methoxyethyl)amine (70 mg, 0.53 mmol) and acetic acid (0.029 ml, 0.51 mmol) were dissolved in 1,2-dichloroethane (5 ml). To the resulting solution was added sodium triacetoxyborohydride (115 mg, 0.515 mmol) at room temperature. The resulting mixture was stirred at room temperature for 3 days. To the reaction mixture were added a saturated aqueous solution of sodium bicarbonate and ethyl acetate. The resulting mixture was separated into layers. The organic layer thus obtained was washed sequentially with a satu-rated aqueous solution of sodium bicarbonate and brine, and dried over anhydrous magnesium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue thus obtained was subjected to flash silica gel chromatography. The fraction obtained from the hexane:ethyl acetate=3:2 eluate was concentrated under reduced pressure to afford a white solid. The resulting solid was washed with hexane to give the title compound (101 mg, 0.192 mmol, 78%) as a white powder. 1H-NMR(400MHz,CDCl3) delta: 2.73(4H,t,J=5.8Hz), 3.31(6H,s), 3.47(4H,d,J=5.8Hz), 3.75(2H,s), 5.93(1H,s); 6.88-6.97(1H,m), 6.97-7.07(1H,m), 7.38(2H,d,J=8.8Hz), 7.50-7.60(3H,m), 7.76(1H,dd,J=8.1,2.0Hz), 7.98-8.08(1H,m), 8.54(1H,d,J=2.0Hz). MSm/z: 525(M++H).

Statistics shows that Bis(2-methoxyethyl)amine is playing an increasingly important role. we look forward to future research findings about 111-95-5.

Reference:
Patent; DAIICHI PHARMACEUTICAL CO., LTD.; EP1640366; (2006); A1;,
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Adding a certain compound to certain chemical reactions, such as: 74137-36-3, name is 1,3-Dibromo-5-methoxybenzene, 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 74137-36-3, Application In Synthesis of 1,3-Dibromo-5-methoxybenzene

2 mmol 3,5-dibromoanisole were dissolved in 10 ml THF and cooled to -78C. 2.4 mmol of n- BuLi were added dropwise and stirring was continued for 15 min. 3 mmol of methyl iodide were added and the mixture was allowed to slowly warm to ca. -200C over a period of ca. 2 h. IM HCl and dichloromethane were added and the phases were separated. 1.65 mmol of crude 3-bromo-5- methylanisole were taken to the next step without further purification.

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; KARO BIO AB; WO2008/43567; (2008); A1;,
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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 393-15-7 as follows. Recommanded Product: 393-15-7

Benzoic acid Z-17a (1.1 g, 3.0 mmol) is suspended in thionyl chloride and stirred for 1 h at 60 C. The reaction mixture is evaporated down and dried azeotropically with dry toluene. The acid chloride Z-18a (400 mg, 1.04 mmol) is then taken up in a little NMP (1.2 mL) and combined with 4-methoxy-3-trifluoromethyl-phenylamine E-2a (188 mg, 1.55 mmol) and DIPEA (300 muL, 1.75 mmol). For working up water is added, the precipitate obtained is filtered off, dried and Example compound III-2 (HPLC-MS: tRet.=2.20 min; MS (M+H)+=540) is obtained.

According to the analysis of related databases, 393-15-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2012/94975; (2012); A1;,
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Application of 2393-23-9, A common heterocyclic compound, 2393-23-9, name is 4-Methoxybenzylamine, molecular formula is C8H11NO, 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.

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.

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; GALAPAGOS NV; Menet, Christel Jeanne Marie; Mammoliti, Oscar; Blanc, Javier; Orsulic, Mislav; Roscic, Maja; (81 pag.)US9440929; (2016); B2;,
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Electric Literature of 645-36-3, 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 645-36-3 as follows.

N- (2-chloropyridine-4-substituted) -4-fluorobenzamide (5g, 19.9mmol) was dissolved in toluene (50mL), cooled to 0 C, and dichlorosulfoxide was slowly added dropwise under nitrogen protection. (7.1 g, 59.8 mmol), transferred to room temperature for 1 hour, and then refluxed overnight. TLC monitoring. After the reaction was completed, the solvent and dichlorosulfoxide were removed to obtain (Z) -N- (2-chloropyridine-4-substituted) -4-fluorobenzimidyl chloride.Dissolve aminoacetaldehyde diethanol (3.5 g, 23.9 mmol) and TEA (4.0 g, 39.8 mmol) in dichloromethane (100 mL), cool to 0 C, and obtain (Z) -N- (2-chloropyridine-4-substituted) -4-fluorobenzimidyl chloride was dissolved in dichloromethane (100 mL), and the solution was slowly added dropwise. The mixture was naturally warmed to room temperature and stirred overnight. Monitored by TLC. After the reaction was completed, the mixture was washed with a saturated ammonium chloride aqueous solution and a saturated saline solution, dried over anhydrous Na2SO4, filtered, and dried. Purification by silica gel column chromatography gave a yellow solid (7 g, 95.7%).

According to the analysis of related databases, 645-36-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Southern Medical University; Zhang Jiajie; Yang Haikui; Wu Shaoyu; Tian Yuanxin; Wan Shanhe; Zhang Tingting; Wu Xiaoyun; Li Zhonghuang; Jiang Ying; Yan Ruohong; Zhu Zhengguang; Hu Xiang; (75 pag.)CN110041302; (2019); A;,
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Adding a certain compound to certain chemical reactions, such as: 1663-61-2, name is (Triethoxymethyl)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 1663-61-2, Application In Synthesis of (Triethoxymethyl)benzene

To a suspension of triol 11 (3.0 g, 9.2 mmol) in dry MeCN (100 mL), camphor-10-sulfonic acid (880 mg, 3.7 mmol) and triethylorthobenzoate (8.2 mL, 38.6 mmol), were added. The mixture was stirred at rt for 12 h and Et3N (1.5 mL) was added to neutralize the solution. The mixture was then evaporated to dryness and the residue was diluted with DMF (100 mL). NaH (60percent dispersion in mineral oil, 542 mg, 18.4 mmol) was added at 0 °C followed by dropwise addition of BnBr (1.8 mL, 16.6 mmol). The reaction mixture was stirred at rt for 2 h and the excess of sodium hydride was neutralized by dropwise addition of MeOH (20 mL) at 0 °C. The mixture was then evaporated to dryness and the residue was dissolved with EtOAc. The organic phase was washed with water and then with 2 M aqueous HCl (.x.3). The opening of the orthoester was checked by TLC. The organic phase was dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by flash chromatography using cyclohexane/EtOAc (98:2–>9:1) as eluent to give 5 (2.2 g, 46percent) and its beta-anomer 2-methyl-5-tert-butylphenyl 2-O-benzoyl-4-O-benzyl-1-thio-beta-l-rhamnopyranoside (340 mg, 7percent) as colorless oils. (alpha anomer) Rf 0.42 (cyclohexane/EtOAc 8:2); [alpha]D -93 (CHCl3, c 0.7); 1H NMR (300 MHz, CDCl3) delta 8.24-7.27 (m, 13H, SC6H3C(CH3)3CH3, OCH2C6H5, OCOC6H5), 5.82 (dd, 1H, J1,2 = 1.3 Hz, J2,3 = 3.3 Hz, H-2), 5.66 (br s, 1H, H-1), 5.11 (d, 1H, JA,B = 11.2 Hz, A part of an AB system, OCHHC6H5), 4.93 (d, 1H, JA,B = 11.2 Hz, B part of an AB system, OCHHC6H5), 4.55-4.43 (m, 2H, H-3, H-5), 3.78 (t, 1H, J3,4 = J4,5 = 9.2 Hz, H-4), 2.59 (s, 3H, SC6H3C(CH3)3CH3), 1.59 (d, 3H, J5,6 = 5.9 Hz, H-6), 1.46 (s, 9H, SC6H3C(CH3)3CH3); 13C NMR (75 MHz, CDCl3) delta 166.4 (OCOC6H5), 149.8, 138.4, 137.0, 133.5, 133.0, 132.9, 130.2, 130.1, 130.0, 129.7, 128.7, 128.6, 128.5, 128.3, 128.1, 127.6, 125.2, 124.0, (SC6H3C(CH3)3CH3, OCOC6H5, OCH2C6H5) 85.8 (C-1), 81.8 (C-2), 75.6 (C-4), 75.3 (OCH2C6H5), 71.3 (C-3), 69.0 (C-5), 34.6 (SC6H3C(CH3)3CH3) 31.5 (SC6H3C(CH3)3CH3), 20.5 (SC6H3C(CH3)3CH3), 18.3 (C-6); HR-ESI-MS m/z calcd for C31H36O5S 543.2175 [M+Na]+, found 543.2160.

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, (Triethoxymethyl)benzene, other downstream synthetic routes, hurry up and to see.

Reference:
Conference Paper; Milhomme, Ophelie; Dhenin, Sandrine G.Y.; Djedaini-Pilard, Florence; Moreau, Vincent; Grandjean, Cyrille; Carbohydrate Research; vol. 356; (2012); p. 115 – 131;,
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Reference of 645-36-3,Some common heterocyclic compound, 645-36-3, name is 2,2-Diethoxyethanamine, molecular formula is C6H15NO2, 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 35 g of P8 in 354 ml of MeOH (methanol) was added 3.5 ml of AcOH (acetic acid). The solution was mixed with 33 ml of aminoacetaldehyde diethylacetal at room temperature and stirred for 3-4 hrs. After the solution was cooled to 10 s C, 3.3 g of the reducing agent NaBH4 (sodiumborohydride) was slowly added thereto. At this time, care had to be taken because of hydrogen gas generation and exothermal reaction. The solution was stirred at room temperature for 1 hr. When the reaction was completed, 354 ml of EA (ethylacetate) and 354 ml of distilled water were added so as to separate layers. The organic layer thus formed was dried over 141 g of MgSO4 (magnesium sulfate) and crystallized in hexane to afford 85 g of P7 as a yellowish solid (yield 80%) . 1H NMR (500MHz, CDCl3), delta 8.36 (d, J=4.8 Hz, IH), delta 7.61 (s, IH), delta 7.17 (d, J=4.2 Hz, IH), delta 7.10 (d, J=4.2 Hz, IH), delta 4.58 (t, J=3.3, IH), delta 4.21 (s, 3H), delta 4.07 (s, 3H), delta 3.68 (m, 2H), delta 3.51 (m, 2H), delta 2.82 (d, J=3.3 Hz, 2H), delta 2.48 (s, 3H), delta 1.19 (t, J=4.2 Hz, 6H).

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

Reference:
Patent; CHOONGWAE PHARMA CORPORATION; WO2010/120112; (2010); A2;,
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Reference of 102-52-3,Some common heterocyclic compound, 102-52-3, name is 1,1,3,3-Tetramethoxypropane, molecular formula is C7H16O4, 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.

100 mg (0.215 mmol) of Example 12 A were mixed with 1.00 mL (6.07 mmol) 1, 1,3,3- tetramethoxypropane. The reaction mixture was heated to 175C for lh using a microwave oven. The reaction mixture was treated with DCM/MeOH and one drop of triethylamine. The solvents were removed under reduced pressure. The mixture was purified by preparative HPLC (eluent A: water + 0.13 % TFA, eluent B: MeOH) yielding 45 mg (54 %) of the title compound.HPLC-MS (Method 3): R, = 1.36 minMS (ESI pos): m/z = 387 (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 1,1,3,3-Tetramethoxypropane, its application will become more common.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; HEINE, Niklas; EICKMEIER, Christian; FERRARA, Marco; GIOVANNINI, Riccardo; ROSENBROCK, Holger; SCHAENZLE, Gerhard; WO2012/20022; (2012); 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. 1535-73-5, name is 3-Trifluoromethoxyaniline, A new synthetic method of this compound is introduced below., category: ethers-buliding-blocks

Example 32 7-(2,4-dimethoxypyrimidin-5-yl)-4-((3-(trifluoromethoxy)phenyl)amino)quino sulfonamide To a suspension of 4-chloro-7-(2,4-dimethoxypyrimidin-5-yl)quinoline-3- sulfonamide (50 mg, 0.131 mmol) in acetic acid (10 ml.) was added 3- (trifluoromethoxy)aniline (23.26 mg, 0.131 mmol). The reaction mixture was stirred at room temperature overnight and was purified by reverse-phase preparative HPLC (YMC 75 X 30 mm column, acetonitrile/water + 0.1 percent trifluoroacetic acid) to afford 7-(2,4- dimethoxypyrimidin-5-yl)-4-((3-(trifluoromethoxy)phenyl)amino)quinoline-3-sulfonamide, trifluoroacetic acid salt (24 mg, 0.038 mmol, 28.8 percent yield) as a yellow solid. 1 H NMR (400 MHz, METHANOL-d4) delta ppm 4.08 (s, 3 H) 4.12 (s, 3 H) 7.37 – 7.48 (m, 3 H) 7.60 – 7.75 (m, 3 H) 8.28 (s, 1 H) 8.53 (s, 1 H) 9.16 (s, 1 H). LCMS (ES+) m/e 522 [M+H]+.

The synthetic route of 1535-73-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE LLC; BROWN, Kristin, K.; CHAI, Deping; DODSON, Christopher, S.; DUFFY, Kevin, J.; SHAW, Antony, Nicholas; WO2013/96151; (2013); A1;,
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