Category: ethers-buliding-blocks

Application of 651734-54-2,Some common heterocyclic compound, 651734-54-2, name is 2,6-Difluoro-3,5-dimethoxyaniline, molecular formula is C8H9F2NO2, 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.

Potassium bis(trimethylsilyl)amide 1 M in THF (71 mL; 70 mmol) was added drop wise at 0C to a solution of 2,6-difluoro-3,5-dimethoxyphenylamine (8.9 g; 46.9 mmol) in DMF (220 mL). The reaction mixture was stirred at 0C for 1 hour. Then; intermediate 5 (12 g; 39 mmol) was added portion wise at 0C and the reaction mixture was stirred at room temperature for 24 hours. The reaction mixture was poured into ice water and brine. EtOAc was added. The mixture was stirred at room temperature for 30 minutes, then filtered through a pad of Celite. The filtrate was extracted with EtOAc. The organic layer was washed with brine, dried over MgS04, filtered and evaporated to dryness. The residue was taken-up with Et20, the precipitate was filtered and dried to give 14 g (90%) of intermediate 12.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2,6-Difluoro-3,5-dimethoxyaniline, its application will become more common.

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; BERDINI, Valerio; SAXTY, Gordon; ANGIBAUD, Patrick Rene; QUEROLLE, Olivier Alexis Georges; PONCELET, Virginie Sophie; ROUX, Bruno; MEERPOEL, Lieven; WO2013/61080; (2013); A1;,
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Related Products of 2062-98-8, A common heterocyclic compound, 2062-98-8, name is Perfluoro(2-methyl-3-oxahexanoyl) fluoride, molecular formula is C6F12O2, 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: The methyl perfluoroalkyl ether carboxylate was prepared by esterfication of perfluorinated ether acid fluoride with methanol. A mixed solution of 41.11 g anhydrous triethylamine (0.40 mol) in 47.5 g anhydrous methanol (1.48 mol) was added dropwise into 185 g perfluoro-2,5-dimethyl-3,6-dioxa-nonanoic acid fluoride (0.37 mol) in a dry three-neck flask under agitation over a period of 2 h at 0 C. The mixture was agitated for another 4 h and the temperature of reaction mass was maintained at room temperature. Subsequently, the reaction mixture was poured into a separating funnel. The fluorocarbon layer was washed with sodium bicarbonate solution and dried over anhydrous sodium sulfate to obtain the crude product. The crude product was distilled to give 178.43 g methyl perfluoro-2,5-dimethyl-3,6-dioxa-nonanoate (yield 94%) boiling at 145 C at 760 mmHg. IR: 2969,1792, 1290, 1237, 1145, 1040, 994 cm-1. 1H-NMR (500 MHz, CDCl3): delta 3.99 (3H, s, CH3). 13C-NMR (125 MHz, CDCl3): delta 54.60 (-CH3-).

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; Shi, Xiang; Shi, Hongxin; Wu, Hongke; Shen, HaiMin; Research on Chemical Intermediates; vol. 44; 9; (2018); p. 5091 – 5105;,
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Synthetic Route of 1484-26-0, A common heterocyclic compound, 1484-26-0, name is 3-Benzyloxyaniline, molecular formula is C13H13NO, 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.

N4- [3-(BENZYLOXY) PHENYL]-N6,N6-DIMETHYL-2-(METHYLSULFANYL)-4,6-PYRIMIDINEDIAMINE: A mixture of 3-(benzyloxy)aniline (5.13 g) and NaH (1.37 g) in tetrahydrofuran (15 mL) was refluxed for 30 minutes and then cooled to room temperature. A solution of N-[6-chloro-2-(methylsulfanyl)-4-pyrimidinyl]-N,N-dimethylamine (3.5 g) in tetrahydrofuran (35 mL) was added to this mixture and the resulting solution was stirred for 22.5 hours. The reaction mixture was quenched with saturated NH4Cl. Then the crude product was concentrated under reduced pressure and redissolved in EtOAc. The organic layer was separated and washed with aqueous citric acid (2.x.300 mL), water (2.x.300 mL) and brine (2.x.300 mL). The crude product was purified by column chromatography [eluent: EtOAc/hexane (1:4)], giving the desired product (5.9 g, 94percent).

The synthetic route of 1484-26-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Packiarajan, Mathivanan; US2004/82587; (2004); A1;,
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Synthetic Route of 24988-36-1, 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. 24988-36-1, name is 1,5-Dibromo-2,4-dimethoxybenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Add to the dry three-necked flask with a magnetic rotor 1,3-dibromo-4,6-dimethoxybenzene (2.5000 g, 8.53 mmol, 1.0 eq.),4-tert-butylbenzeneboronic acid (3.1890 g, 17.92 mmol, 2.1 eq.),tetrakistriphenylphosphine palladium (0.9820 g, 0.85 mmol, 0.1 equivalent) and potassium carbonate (4.7160 g, 34.1 mmol, 4.0 eq.).Nitrogen gas was purged three times, then 1,4-dioxane (30 mL) and water (10 mL) were added under nitrogen.The three vials were then placed in a 110 C oil bath.After stirring for 48 hours, the reaction was monitored by thin layer chromatography. After cooling to room temperature, the organic phase was separated and aqueous was extracted with ethyl acetate (30mL×2). All the organic phases were combined, dried over anhydrous sodium sulfate, filtered, and concentrated, and then the crude product was purified by silica gel column chromatography (eluent: petroleum ether / ethyl acetate = 20/1-10/1) to obtain A3 , white solid 3.4040 g, yield 99%.

The synthetic route of 1,5-Dibromo-2,4-dimethoxybenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Zhejiang University of Technology; Li Guijie; Dai Jianxin; Chen Shaohai; Feng Qi; (28 pag.)CN110183476; (2019); A;,
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Some common heterocyclic compound, 93919-56-3, name is (4-(Trifluoromethoxy)phenyl)methanamine, 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. Recommanded Product: 93919-56-3

(a) N-(4-Trifluoromethoxy-benzyl)-2,2-dimethyl-propionamide A solution of pivaloyl chloride (2.1 mL, 17 mmol) in MeCN (10 mL) was added dropwise over 10 min to a solution of 4-trifluoromethoxy-benzylamine (2.6 mL, 17 mmol) and TEA (4.0 mL, 29 mmol) in MeCN (20 mL) at 0 C. The mixture was stirred for 30 min, filtered and concentrated. The residue was treated with water and filtration gave the sub-title compound. Yield: 4.12 g (88%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 93919-56-3, its application will become more common.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2012/309738; (2012); A1;,
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Related Products of 41406-00-2, A common heterocyclic compound, 41406-00-2, name is 3-Isopropoxyaniline, molecular formula is C9H13NO, 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: Thiazole bisamide compounds were prepared in the same manner as in Examples 1-28 except that the R3 diphenyl ether group was substituted with a substituted phenyl group as shown in Table 5, The results of the prepared products of formula as (I-3), as well as the numbers of the prepared compounds, R1, R2 and R7 and the yields thereof are shown in Table 5. The intermediate of formula (II) (0.5 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI, 0.6 mmol), hydroxybenzotriazole (HOBt, 0.6 mmol) was dissolved in 5 mL of N, N-dimethylformamide, the reaction temperature 25 deg. C 1h; Then, the reactant (0.6 mmol) represented by R3-NH2 was added to the above solution, the reaction temperature was 25 deg. C 72h; after completion of the reaction, the solvent was removed under reduced pressure, column chromatography to obtain the target product, thiazole bisamide compound.

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; Central China Normal University; Yang, Guangfu; Chen, Cheng; Chen, Yanqing; Xiong, Maoqian; (30 pag.)CN106316977; (2017); A;,
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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. 332-48-9, name is 1-(2-Bromoethoxy)-4-fluorobenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Safety of 1-(2-Bromoethoxy)-4-fluorobenzene

Dissolve methyl 4-((15)-l-(((2R)-pyrrolidin-2-carbonyl)amino)ethyl)benzoate hydrochloride (1.00 g, 3.2 mmol) in DMF (8.0 mL) at room temperature, then add K2CO3 (1.33 g, 9.6 mmol) and l-(2-bromoethoxy)-4-fluorobenzene (715 mg, 3.2 mmol), then heat the mixture to 100 C with stirring overnight. Dilute the mixture with EtOAc (100 mL), and wash with a saturated aqueous solution of NaCl (2 chi 75 mL). Discard the aqueous layers, and dry the organic layer over MgS04, filter, and concentrate under reduced pressure to a volume of ca. 10 mL. Add hexanes (100 mL, then collect the resulting precipitate by filtration and rinse with hexanes (25 mL) and air-dry to furnish the title compound as a white solid (750 mg, 57% yield). Mass spectrum (m/z): 415 (M + H)+.

The synthetic route of 332-48-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ELI LILLY AND COMPANY; FISHER, Matthew Joseph; KUKLISH, Steven Lee; MANNINEN, Peter Rudolph; SCHIFFLER, Matthew Allen; WARSHAWSKY, Alan M; YORK, Jeremy Schulenburg; WO2015/94902; (2015); 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. 93919-56-3, name is (4-(Trifluoromethoxy)phenyl)methanamine, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: (4-(Trifluoromethoxy)phenyl)methanamine

To a solution of 3-chloro-4-{[(5-chloro-l,3-thiazol-2-yl)amino]sulfonyl}benzoic acid (Preparation 35, 200mg, 0.57,mmol, leq) in THF (5ml) was added Et3N (0.116ml, 0.85mmol, 1.5eq), l-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI HCl, 141mg, 0.62mmol, l.leq), 1-hydroxybenzotriazole hydrate (HOBt, 77mg, 0.57mmol, l.Oeq) and an amine (0.62mmol, l.leq) at 00C. The reaction mixture was stirred at 25C for 16 hours. The reaction mixture was extracted from 2M HCl into DCM and the solvent evaporated in vacuo. The crude material was purified by preparative HPLC to yield the title compound.

According to the analysis of related databases, 93919-56-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ICAGEN, INC.; PFIZER LIMITED; WO2008/118758; (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 111-95-5 as follows. Recommanded Product: Bis(2-methoxyethyl)amine

To a 0 C solution of compound 1(300 mg, 0.73 mmol), HATLI (698 mg,1.84 mmol), HOBt (205 rng, 1.84 rnmol) and DIPEA (379 mg, 2.79 mmol) in 3 rnLof DMF was added compound 2 (139 mg, 1.35mmol), The mixture was stirred at the room temperature for I h. Then the resulting solution was diluted with water (15 rnL and ethyl acetate (15 rnL. The layers were separated and the aqueous phase was extracted with ethyl acetate (15 rnL x 2). The combined organic layers weredried over anhydrous Na2SO4, concentrated and the residue was purified by flash column on silica gel eluted with petroleum ether and EtOAc to give the compound 3 (170 mg, 35%) as yellow solid. LCMS (M+H) m/z: cacld 638.8, found 638.9.

According to the analysis of related databases, 111-95-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CLEAVE BIOSCIENCES, INC.; ZHOU, Han-Jie; WUSTROW, David; WO2014/66506; (2014); A2;,
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Reference of 54314-84-0, These common heterocyclic compound, 54314-84-0, name is ((3-Bromopropoxy)methyl)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.

Benzyl-3-bromopropyl ether(175 mL, 1.00 mmol) was dissolved in dimethylformamide(1 mL).N- (benzyloxycarbonyl) acetamide potassium salt(256 mg, 1.10 mmol), and the mixture was stirred at room temperature for 23 hours.The reaction was terminated by adding saturated aqueous ammonium chloride solution (about 3 mL)The reaction mixture was extracted with ethyl acetate.After washing the organic layer with water and saturated brine,And dried over anhydrous magnesium sulfate.Flash silica gel chromatography(10percent ethyl acetate / n-hexane)A colorless oil of N- (3- (benzyloxy) propyl) -N- (benzyloxycarbonyl) acetamide (311 mg, 91percent) was obtained.

Statistics shows that ((3-Bromopropoxy)methyl)benzene is playing an increasingly important role. we look forward to future research findings about 54314-84-0.

Reference:
Patent; School corporation Meijo University; Mori, Yuji; Sakai, Takeo; Fukuda, Ayumi; Kasai, Satomi; (28 pag.)JP2018/95576; (2018); A;,
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