Tag: M.W=100-200

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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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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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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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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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. 22236-10-8, name is 4-(Difluoromethoxy)aniline, A new synthetic method of this compound is introduced below., SDS of cas: 22236-10-8

Preparation 9 6-Chloro-N*4*-(4-difluoromethoxyphenyl)-2-methylpyrimidine-4,5-diamine; 4,6-dichloro-2-methyl-pyrimidin-5-ylamine (20.0 g, 110 MoI) was added with stirring to EtOH (80 mL) over 3 minutes to give complete solution. 4-Difluoromethyoxyaniline (18.8 g, 118 MoI) was then added with stirring over 3 minutes. A dark brown solution was observed. EtOH (20 mL) was then added followed by a premixed solution of c.HCI (10 mL) in EtOH (40 mL) at a steady rate over 20 minutes. A slight exotherm up to approx 2O0C was noted. The solution was then warmed to 850C and held at that temperature for 4 hours. The reaction mixture was then cooled to room temperature, and a beige solid precipitated. This reaction mixture was filtered then washed with EtOH (100 ml_) followed by MTBE (3OmL) to remove EtOH traces. The resultant solid was dried in vacuo over the weekend to give the title compound, as the hydrochloride salt, as a beige solid (17.2 g, 45%) 1H NMR (400MHz, CD3OD) delta = 2.55 (s, 3H), 6.89 (t, 1 H), 7.27 (d, 2H), 7.75 (d, 2H) LCMS (System 4) 3.07 mins; m/z (APCI) = 301 [MH+]

The synthetic route of 22236-10-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER LIMITED; WO2009/144632; (2009); A1;,
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Reference of 393-15-7,Some common heterocyclic compound, 393-15-7, name is 4-Methoxy-3-(trifluoromethyl)aniline, 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.

4-Methoxy-3-trifluoromethyl-phenylamine (5 g, 26 mmol) in 12 mL water was cooled to -5 degrees C. (Ice/Methanol bath). Conc. HCl was added dropwise (7 ml), and the reaction mixture was stirred for five minutes. A solution of NaNO2 (2.0 g, 29 mmol) dissolved in 3 ml water was added dropwise over 10 minutes, and the reaction mixture was stirred for 30 min. Sodium acetate (1.8 g, 22 mmol) was then added, and stirring was continued at -5 degrees C. In a separate flask, ethyl alpha-acetoacetate (4.55 g, 29 mmol) in 20 ml absolute ethanol was stirred, and KOH (1.6 g, 29 mmol) dissolved in 3 ml water was added, followed by ice (30 g). The resulting diazonium salt was added quickly to the reaction mixture, rinsing in with 5 ml EtOH, and the reaction mixture was stirred at zero degrees C. for 3.5 hours, then stored at -10 C) for 16 hours. The reaction mixture was warmed to room temperature and extracted with ethyl acetate, washed with brine, and dried over magnesium sulfate. Solvent was removed under reduced pressure to leave a liquid residue. In a separate flask 100 ml EtOH and 21 ml acetyl chloride were mixed, with cooling in an ice bath, then heated to 70 degrees C. The liquid residue was added via pipette over 15 minutes to the acetyl chloride solution. This reaction mixture was heated to reflux for 2.5 hours, cooled, evaporated under reduced pressure. The residue was purified by column chromatography (10% ethyl acetate/hexane) to give 3.0 g 5-Methoxy-3-methyl-6-trifluoromethyl-1H-indole-2-carboxylic acid ethyl ester, 38% as a white solid and triturated with diethyl ether to give 5-Methoxy-3-methyl-6-trifluoromethyl-1H-indole-2-carboxylic acid ethyl ester (1.0 g) as a white solid, and 5-Methoxy-3-methyl-4-trifluoromethyl-1H-indole-2-carboxylic acid ethyl ester (14%) as a white solid.

The synthetic route of 393-15-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Roche Palo Alto LLC; US2007/49609; (2007); A1;,
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102-52-3, name is 1,1,3,3-Tetramethoxypropane, 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. category: ethers-buliding-blocks

Stage 5- Preparation of 3-(phenylamino)allylidene)aniline hydrochloride (Bioorg. Med. Chem. 2006, 4, 92-97). Compound having formula (VI) where n=1. 24.7 g of aniline in solution in 300 mL of 0.75 N HCl is added drop by drop to 21.8 g of 1,1,3,3-tetramethoxypropane in solution in 300 mL of 0.75 N HCl. The appearance of an intense orange colour and the precipitation of an orange crystalline solid are observed. The medium is then left under stirring for 3 hours at 50 C. The cooled medium is filtered, vacuum-dried to obtain 15.2 g of orange solid (Yd=44.2%). C15H14N2, HCl-(Mass ESI+400 C. MH+=223.1).

The synthetic route of 102-52-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE (CNRS); PIERRE FABRE MEDICAMENT; Guminski, Yves; Imbert, Thierry; Pesnel, Sabrina; Pillon, Arnaud; Le Pape, Alain; Lerondel, Stephanie; US2013/183247; (2013); A1;,
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Synthetic Route of 929-75-9, These common heterocyclic compound, 929-75-9, name is 1,11-Diamino-3,6,9-trioxaundecane, 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 two-neck flask equipped with a magnetic stirrer and reflux condenser, flushed with dry argon, was charged with diazacrown derivative 4-9 (0.2-0.25 mmol), Pd(dba)2 (8-16 mol%), BINAP or DavePhos ligand (9-18 mol%), absolute dioxane (10-12 mL), the reaction mixture was stirred for several minutes, then the corresponding polyamine (0.2-0.25 mmol) and NaOt-Bu (0.6-0.75 mmol) were added, and the reaction mixture was stirred at reflux for 24 h. After cooling down to room temperature the residue was filtered off, washed with CH2Cl2 (5-10 mL), the combined organic fractions were evaporated in vacuo, the residue was dissolved in CH2Cl2 (10 mL), washed with distilled water (3 × 10 mL), dried over 4A molecular sieves, and the solvent was evaporated in vacuo. The solid residue was chromatographed on silica gel (40-60 mum) using a sequence of eluents: CH2Cl2, CH2Cl2-MeOH 100:1-3:1, CH2Cl2-MeOH-NH3(aq) 100:20:1-10:4:1.

The synthetic route of 929-75-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yakushev, Alexei A.; Chernichenko, Nataliya M.; Anokhin, Maxim V.; Averin, Alexei D.; Buryak, Alexei K.; Denat, Franck; Beletskaya, Irina P.; Molecules; vol. 19; 1; (2014); p. 940 – 965;,
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Electric Literature of 39021-83-5, The chemical industry reduces the impact on the environment during synthesis 39021-83-5, name is 1,4-Dimethoxy-2,3-dimethylbenzene, I believe this compound will play a more active role in future production and life.

General procedure: A 100-mL round-bottomed flask was charged with 6 g of silica gel and set up tostir vigorously. Then, a solution of 2.75 g of cerium ammonium nitrate (CAN) (5.0mmol) in water (2.5 mL) was added dropwise. The stirring continued until a freeflowingyellow solid was obtained. DCM (25 mL) was then added to the flask. Thecorresponding substrates where dissolved in 2 mL of DCM and added to the stirredreaction mixture. The reaction was monitored by TLC and after complete consumptionof the starting materials the mixture was filtered through a sintered-glass funnel. Thesolid was washed with about 75 mL of DCM. After solvent removal the quinones wereobtained with high purity. 2,3-Dimethyl-1,4-benzoquinone (46): 1,4-dimethoxy-2,3-dimethylbenzene(43)6 (1 mmol, 166 mg) was used. 46 was obtained without the need of purification (85mg, 63% yield) as an orange powder; m.p. (C) = 54.9-56.4 (Petrol/CH2Cl2); HRMS(EI+): 136.0569 [M]+. Cald. for [C8H8O2]: 136.0524; 1H NMR (400 MHz, CDCl3) delta:6.70 (s, 2H), 2.01 (s, 6H); 13C NMR (100 MHz, CDCl3) delta: 187.4, 141.0, 136.2, 12.2.Data are consistent with those reported in the literature.

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, 1,4-Dimethoxy-2,3-dimethylbenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Jardim, Guilherme A.M.; Silva, Thaissa L.; Goulart, Marilia O.F.; de Simone, Carlos A.; Barbosa, Juliana M.C.; Salomao, Kelly; de Castro, Solange L.; Bower, John F.; da Silva Junior, Eufranio N.; European Journal of Medicinal Chemistry; vol. 136; (2017); p. 406 – 419;,
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Adding a certain compound to certain chemical reactions, such as: 70894-71-2, name is N-(4-Methoxybenzyl)cyclopropanamine, 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 70894-71-2, category: ethers-buliding-blocks

General procedure: N-cyclopropyl-N-substituted benzylamine (4.0 mmol) inethanol was mixed with carbon disulfide (4.0 mmol) under ice coldcondition. To the resultant yellow dithiocarbamic acid solution,aqueous solution of NiCl2,6H2O (2.0 mmol) was added with constantstirring. The solid which precipitated was washed severaltimes with cold water and then dried (Fig. 1).

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

Reference:
Article; Sathiyaraj; Srinivasan; Thirumaran; Velmurugan; Journal of Molecular Structure; vol. 1102; (2015); p. 203 – 209;,
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