Category: ethers-buliding-blocks

Application of 1484-26-0,Some common heterocyclic compound, 1484-26-0, name is 3-Benzyloxyaniline, molecular formula is C13H13NO, 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 mixture of 2,6-dichloropyrimidine (2.00 g, 13.4 mmol), 3-benzyloxoaniline (2.07 g, 13.4 mmol) and triethylamine (2.72 g, 26.8 mmol) in 1-butanol (20 mL) was stirred at 50¡ã C. for 17 h. The reaction mixture was concentrated to remove most of the 1-butanol, the crude product was preadsorbed onto silica gel using chloroform and purified by flash chromatography (95:5 chloroform/methanol) to afford N4-(3-benzyloxyphenyl)-2-chloro-4-pyrimidineamine (1.70 g, 40percent) as colorless oil: 1H NMR (300 MHz, DMSO-d6) delta 10.2 (s, 1H), 8.16 (d, J=6.0 Hz, 1H), 7.48-7.24 (m, 7H), 7.12 (d, J=9.0 Hz, 1H), 6.78 (m, 2H), 5.11 (s, 2H); ESI MS m/z 312 [C17H14ClN3O+H]+.

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

Reference:
Patent; RIGEL PHARMACEUTICALS, INC.; Singh, Rajinder; Argade, Ankush; Payan, Donald; Molineaux, Susan; Holland, Sacha; Clough, Jeffrey; Keim, Holger; Bhamidipati, Somasekhar; Sylvain, Catherine; Li, Hui; Rossi, Alexander; US2015/266828; (2015); 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 321-28-8 as follows. Quality Control of 1-Fluoro-2-methoxybenzene

1-Fluoro-2-methoxybenzene a13 (0.0126 g, 0.10 mmol), acridine photosensitizer (A) (0.0029 g, 0.005 mmol) and L-valine ethyl ester b1 were added sequentially under argon protection. 0.0218 g, 0.15 mmol), 1,2-dichloroethane (DCE) 2.0 mL.The reaction was irradiated for 48 hours under a 6W blue light at room temperature.After completion of the reaction, the solvent was evaporated under reduced pressure and purified by column chromatography, eluting solvent: (V) petroleum ether / (V) ethyl acetate = 20/1.A yellow liquid (30) (0.0188 g, 95%) was obtained.

According to the analysis of related databases, 321-28-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Central China Normal University; Zhou Shaolin; Shi Weimin; (27 pag.)CN110294685; (2019); A;,
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Related Products of 18800-30-1, These common heterocyclic compound, 18800-30-1, name is 1-Bromo-4-(2-bromoethoxy)benzene, 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 1-bromo-4-(2-bromoethoxy)benzene (19.9 g, 100 mmol; see step (a) above) in THF (120 mL) was portion-wise added t-BuOK (14.0 g, 125 mmol) over 10 min at 0C. After stirring at room temperature for 16 h, the mixture was diluted with ‘water (400 mL) and the product was extracted with light petrol (4×100 mL). The combined organic extracts were washed with brine, dried (Na(at)S04), concentrated and distilled under vacuum to yield the sub-title compound (11.5 g, 58%).

The synthetic route of 18800-30-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BIOLIPOX AB; WO2005/123673; (2005); A1;,
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These common heterocyclic compound, 53087-13-1, name is 1-(Benzyloxy)-3-bromobenzene, 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. Application In Synthesis of 1-(Benzyloxy)-3-bromobenzene

Magnesium strip (1.29 g, 52.8 mmol) in anhydrous THF (50 mL)To the suspension was added iodine which was heated with magnesium.The mixture was refluxed and an approximately 5% solution of 3-bromobenzyl phenol(13.9 g, 52.8 mmol) was added.At the beginning of the reaction, the bromide solution is added dropwise and the mixture is then refluxed again1 hour. The mixture was cooled to about 5 C and a solution of cyclopentanone (4.44 g, 52.8 mmol) in THF (50 mL) was added dropwise. The mixture was stirred at rt for 72 h,The reaction was then quenched with a cooled saturated ammonium chloride solution and extracted with diethyl ether (x3). The organic phase was washed with brine, dried (Na2SO4), filtered and concentrated. The product was purified by silica gel chromatography (isohexane / EtOAc), which gave the title compound (8.5 g, 54%).

The synthetic route of 1-(Benzyloxy)-3-bromobenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MEDIVIR AB; KALAYANOV, GENADIY; TORSSEL, STAFFAN; WAHLING, HORST; (130 pag.)TW2018/15396; (2018); A;,
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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. 61367-43-9, name is cis-4-Methoxycyclohexanamine hydrochloride, A new synthetic method of this compound is introduced below., SDS of cas: 61367-43-9

Compound 1a (60 mg, 0.44 mmol) was dissolved in NMP (1 mL) and was added cis-4-methoxycyclohexan-1-amine hydrochloride (62 mg, 0.51 mmol), DIPEA (114 mg, 0.88 mmol), then was stirred at 100 C for 16 hours. The reaction mixture was cooled to room temperature, and was added to water, extracted with CH2Cl2 (10 mL x 3). The combined organic phase was washed with brine (10 mL), dried over Na2SO4 and filtered, the filtrate was concentrated in vacuo, the crude product was purified via preparative TLC (CH2Cl2/MeOH= 10/1) to afford compound 3b (35 mg, yield 32%) as a pale yellow solid.

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; Hangzhou Innogate Pharma Co., Ltd.; ZHANG, Hancheng; LIU, Shifeng; YE, Xiangyang; (47 pag.)EP3483158; (2019); A1;,
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Reference of 1112210-82-8,Some common heterocyclic compound, 1112210-82-8, name is 1,3-Dibromo-5-isopropoxybenzene, molecular formula is C9H10Br2O, 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.

Synthesis of Intermediate 2)Molecular Weight: 293.98 Molecular Weight: 186.21[00530] In a 3-neck 100 mL round-bottomed flask, intermediate- 1 (3.5 g, 1 eq.) was dissolved in DMF and degassed it for 20-30 min. To this reaction mixture, Zinc Cyanide (1.72 g, 1.2 eq.) and tetrakis (0.705 g, 0.05 eq.) was added. Resulting reaction mixture was stirred at 80-90C and reaction was monitored by TLC using Ethyl acetate: hexane (1 :9) as mobile phase, which shows starting material was consumed after 5 h. Reaction was quenched into ice-water slurry and compound was extracted using ethyl acetate (50 mL x 3), combined organic layer were dried over anhydrous sodium sulfate and concentrated under reduce pressure to give crude compound. The crude material was subjected to column chromatography using silica 60/120 as stationary phase and ethyl acetate :n-Hexane as mobile phase. Compound was eluted in 7% ethyl acetate in Hexane. Fractions containing compound was distilled out using rotary evaporation at 40 C/250 mm Hg to obtain 2.095 g (94.51%). Mass/LCMS: LC-MS purity 92.36%, NMR: Confirmed.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,3-Dibromo-5-isopropoxybenzene, its application will become more common.

Reference:
Patent; KARYOPHARM THERAPEUTICS, INC.; SHECHTER, Sharon; KAUFFMAN, Michael; SANDANYAKA, Vincent, P.; SHACHAM, Sharon; WO2011/109799; (2011); A1;,
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These common heterocyclic compound, 450-91-9, name is 4-Fluoro-2-methoxyaniline, 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. Recommanded Product: 4-Fluoro-2-methoxyaniline

39g material take B1-2, concentrated sulfuric acid was added to 500ml was added under ice-salt bath. Controlling the temperature of the whole solution was stirred below 10C. was added maintaining the temperature below 10C, 1ep potassium nitrate, was stirred overnight at room temperature. The next day, poured into ice water, adjusted with ammonia PH>7, extracted with ethyl acetate, dried and purified through column chromatography to give 44g product.

The synthetic route of 4-Fluoro-2-methoxyaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Zhejiang Tongyuankang Pharmaceutical Co., Ltd.; Wu Yusheng; Geng Yang; Meng Qingguo; Niu Chengshan; Liang Apeng; (18 pag.)CN108558835; (2018); A;,
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Application of 22483-09-6, A common heterocyclic compound, 22483-09-6, name is 2,2-Dimethoxyethanamine, molecular formula is C4H11NO2, 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 solution of amino acetaldehyde dimethyl acetal 2a (10. 514 g, 1.081 mL, 10 mmol), purchased from Alfa Aesa, and an aldehyde (10 mmol) in dry ethanol was placed in a round bottom flask and stirred for 12 h. To that solution, sodium borohydride powder (0.567 g, 15 mmol) was added at 0 C slowly over 5 minutes. the solution was then warmed to room temperature. After stirring for 4 h, the reaction was quenched with 3 drops of water and the mixture was filtered through a pad of celite. The solvent was evaporated under reduced pressure, the residue was extracted with 100 mL of ethyl ether and washed with100 mL of water. The organic layer was dried over MgSO4 anhydrous. Ethyl ether was then evaporated and the resulted viscous liquid was purified by flash column chromatography (SiO2; 4:1 then 3:1 and finally 1:1hexanes/ethyl acetate).

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; Luu, Quang H.; Guerra, Jorge D.; Castaneda, Cecilio M.; Martinez, Manuel A.; Saunders, Jong; Garcia, Benjamin A.; Gonzales, Brenda V.; Aidunuthula, Anushritha R.; Mito, Shizue; Tetrahedron Letters; vol. 57; 21; (2016); p. 2253 – 2256;,
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In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 707-07-3, name is (Trimethoxymethyl)benzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. SDS of cas: 707-07-3

Method 1Methyl-1-(chloroacetyl)-2-oxoindoline-6-carboxylate (12,0 g; 0,045 mol) is suspended in toluene (60 ml) at ambient temperature. Acetic anhydride (16,2 g; 0,157 mol) is added to this suspension. The mixture is heated to not less than 104 C and trimethyl orthobenzoate (20,0 g; 0,108 mol) is added within 60 min. During the addition period and subsequent stirring at the same temperature for 3 h, volatile parts of the reaction mixture are distilled off. The concentration of the reaction mixture is kept constant by replacement of the distilled part by toluene (40 ml). The mixture is cooled down to 5 C, stirred for an additional 1 h and filtrated. The solid is subsequently washed with toluene (14 ml) and with a mixture of toluene (8 ml) and ethyl acetate (8 ml). After drying, 16,3 g (91 ,7 %) of the “chlorenol” compound are isolated as slightly yellow crystals. 1H-NMR (500 MHz, DMSO-de) delta: 8,73 (d, J = 1 ,5 Hz, 1 H, 6-H); 8,09 (d, J = 8,0 Hz, 1 H, 9-H); 7,90 (dd, J = 8,1 ; 1 ,5 Hz, 1 H, 8-H); 7,61 – 7,48 (m, 5 H, 21 -H, 22-H, 23-H, 24-H, 25-H); 4,85 (s, 2 H, 18-H2); 3,89 (s, 3 H, 27-H3); 3,78 (s, 3 H, 15-H3). 13C- NMR (126 MHz, DMSO-d6) delta: 165,9 (C-2 + C16); 103,9 (C-3); 127,4; 128,6; 130,0; 135,4 (C-4 + C-5 + C-7 + C-20); 115,1 (C-6); 126,1 (C-8); 122,5 (C-9); 166,7 (C-10); 173,4 (C-13); 58,4 (C-15); 46,4 (C-18); 128,6 (C-21 + C-22 + C- 24 + C-25); 130,5 (C-23); 52,2 (C-27). MS: m/z 386 (M+H)+. Anal, calcd. for C20Hi6CINO5: C, 62.27; H, 4.18; Cl, 9.19; N, 3.63. Found: C, 62.21 ; H, 4.03; Cl, 8.99; N, 3.52. Method 3Methyl-1-(chloroacetyl)-2-oxoindoline-6-carboxylate (12,0 g; 0,045 mol) is suspended in toluene (60 ml) at ambient temperature. Acetic anhydride (16,2 g; 0,157 mol) is added to this suspension. The mixture is heated to reflux, trimethyl orthobenzoate (20,0 g; 0,108 mol) is added within 40 min and heating is maintained for an additional 3 h. The mixture is cooled down to 0 C and the mother liquor is separated. The solid is subsequently washed with toluene (14 ml) and a mixture of toluene (8 ml) and ethyl acetate (8 ml). After drying 15,3 g (87,3 %) of the “chlorenol” compound are isolated as fawn crystals.

The synthetic route of 707-07-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; WO2009/71524; (2009); A2;,
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These common heterocyclic compound, 93919-56-3, name is (4-(Trifluoromethoxy)phenyl)methanamine, 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. COA of Formula: C8H8F3NO

A mixture of 2- (5-amino-2- (furan-2-yl) -7H-pyrazolo [4, 3-e] [1, 2, 4] triazolo [1, 5-c] pyrimidin-7-yl) -2-phenylacetic acid (50 mg, 0.13 mmol) , (4- (trifluoromethoxy) phenyl) methanamine (29 mg, 0.15 mmol) , HATU (55 mg, 0.15 mmol) and DIPEA (50 mg, 0.39 mmol) in DMF (10 mL) was stirred for 4 hours at RT. The reaction mixture was poured into H 2O (20 mL) and extracted with EtOAc (50 mL x 3) . The combined organic layers were washed with brine, dried over Na 2SO 4, concentrated and purified by column chromatography (petroleum ether/EtOAc =1: 1100%EtOAc) to give target compound (39.3 mg, 55.2%) . 1H NMR (400 MHz, DMSO-d6) delta 8.55 (s, 1H) , 8.24 (s, 1H) , 8.20 (br. s, 2H) , 7.95 (s, 1H) , 7.47 -7.27 (m, 9H) , 7.24 (d, J = 3.2 Hz, 1H) , 6.74 (br. s, 1H) , 6.48 (s, 1H) , 4.45 -4.27 (m, 2H) ppm. MS: M/e 549 (M+1) +.

The synthetic route of (4-(Trifluoromethoxy)phenyl)methanamine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BEIGENE, LTD.; ZHANG, Guoliang; ZHOU, Changyou; (152 pag.)WO2019/196803; (2019); A1;,
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