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. 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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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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Electric Literature of 115144-40-6,Some common heterocyclic compound, 115144-40-6, name is 3,4-Difluoroanisole, molecular formula is C7H6F2O, 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.

Preparation 3; 1-FLUORO-4-METHOXY-2-METHYLSULFANYL-BENZENE; 1, 2-Difluoro-4-methoxy-benzene (100mg, 0. 69MMOL) and sodium methanethiolate (148mg, 2. 08MMOL) were dissolved in N, N-dimethylformamide (2mL) and the reaction mixture stirred at 60C for 18 hours. Additional sodium METHANETHIOLATE (99mg, 139MMOL) was added and the reaction mixture heated to 100C for 18 hours. The reaction mixture was diluted with water and extracted with ether (x2). The ether extracts were washed with water (x2), dried over magnesium sulphate and concentrated in vacuo. The residue was taken up in pentane: ether 1: 1 mixture (2mL) and filtered through a plug of silica in a pipette, washing through with pentane: ether 1: 1 mixture (5mL). The solution was concentrated in vacuo to yield the title product as a colourless oil, 135mg. HNMR (CDC13, 300MHZ) : A = 2.45 (s, 3H), 3.80 (s, 3H), 6.65 (dd, 1 H), 6.80 (dd, 1 H), 6.95 (t, 1 H) ppm

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3,4-Difluoroanisole, its application will become more common.

Reference:
Patent; PFIZER LIMITED; PFIZER INC.; WO2005/9966; (2005); A1;,
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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. 702-24-9, name is 4-Methoxy-N-methylbenzylamine, This compound has unique chemical properties. The synthetic route is as follows., Formula: C9H13NO

A solution of p-methoxybenzylmethylamine (1.11 g; 7.34 mmol) and EtOH (10 mL) was added to a solution of 3,4,6-trichloropyrazine (1.28 g; 6.99 mmol), TEA (0.983 mL; 6.99 mmol) and anhydrous EtOH (20 mL) and the reaction stirred overnight at room temperature. The solvent was evaporated and the residue partitioned between EtOAc and H2O. The phases were separated, the water washed with EtOAc, and the combined EtOAc solutions washed with water and brine. The solution was dried (MgSO4), filtered and evaporated. The product was purified by silica gel chromatography and eluted with an EtOAc:hexane mixture (5:95–>30:70) to yield 89 as a white solid (1.3 g; 62percent).

According to the analysis of related databases, 702-24-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Roche Palo Alto LLC; US2004/198736; (2004); A1;,
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Related Products of 171290-52-1,Some common heterocyclic compound, 171290-52-1, name is 3,5-Dimethoxyphenylacetylene, molecular formula is C10H10O2, 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.

3,5-dimethoxyphenylacetylene 81 mg (0.50 mmol), silver nitrite 154 mg (1 mmol), N-bromosuccinimide 178 mg (1 mmol)10 mL of a pressure-tight sealed container was sequentially added, and 5 mL of 1,2-dichloroethane was further added.The mixture was stirred at room temperature, and the reaction was checked by TLC. The reaction was completed in 8 hours.The reaction solution was diluted with 10 mL of dichloromethane, and filtered to give a clear liquid.Separation by column chromatography (extraction of petroleum ether/ethyl acetate in a volume ratio of 100:1)The eluate containing the desired product were collected and the solvent was evaporated to give a white solid 3,5-dimethoxy-benzonitrile 42.4mg (52% yield).

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-Dimethoxyphenylacetylene, its application will become more common.

Reference:
Patent; Zhejiang University of Technology; Liu Yunkui; Zhang Jian; Bao Hanyang; (9 pag.)CN107641088; (2018); A;,
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Reference of 19500-02-8, 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. 19500-02-8, name is 3-Methoxy-2-methylaniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Part A Preparation of N-tert-butoxycarbonyl-3-methoxy-2-methylaniline. A solution of 44.4 g (344 mmol) of 3-methoxy-2-methylaniline and 75 g (344 mmol)of di-tert-butyl dicarbonate in 400 mL of THF was heated to maintain reflux for 4 hours. After concentrating at reduced pressure, the residue was taken up in ethyl acetate, washed with iN citric acid, water and dried (MgSO4). After removing the solvent at reduced pressure, the residue was crystallized from hexane to give 64.5 g (84percent yield) of N-tert-butoxycarbonyl-3-methoxy-2-methylaniline, mp, 56-57¡ã C. Analysis for C13H19NO3: Calculated: C, 65.80; H, 8.07; N, 5.90 Found: C, 63.32; H, 7.83; N, 5.56.

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, 3-Methoxy-2-methylaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Eli Lilly and Company; US6274578; (2001); B1;,
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Related Products of 1758-46-9, A common heterocyclic compound, 1758-46-9, name is 2-Phenoxyethylamine, 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.

General procedure: To 2.45mmol of carboxylic acid derivatives (47) dissolved in 0.7mL of dry pyridine were added 0.1mL of phosphorous oxychloride. The mixture was led to?10¡ãC and then was added 39.2mmol of the appropriate amine or alcohol. The reaction was stirred at room temperature for 16h, then was added water and the product extracted with ethylacetate. The organic layer was washed with a NaHCO3 solution, dried and concentrated. The residue was purified by flash chromatography (Ethyl acetate 9: Light Petroleum 1).

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; Federico, Stephanie; Margiotta, Enrico; Salmaso, Veronica; Pastorin, Giorgia; Kachler, Sonja; Klotz, Karl-Norbert; Moro, Stefano; Spalluto, Giampiero; European Journal of Medicinal Chemistry; vol. 157; (2018); p. 837 – 851;,
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