Tag: M.W=100-200

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;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem