Month: July 2021

Related Products of 150-78-7, 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. 150-78-7, name is 1,4-Dimethoxybenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: Examples 17 to 44 show the versatility of the method with diferent compounds (0203) ALKYLCOMPSUBST and FCLALKYLHALIDES, they were done in analogy to example 1 , reaction conditions were 0.2 mmol of FCLALKYLHALIDE, CAT was Pt/C (Pt: 5 mol % relative to FCLALKYLHALIDE) and Cs2C03(l molar equivalent based on (0204) FCLALKYLHALIDE). ALKYLCOMPSUBST was used in the amount of 0.5 mL in case of a ALKYLCOMPSUBST being liquid and 1 mmol in case of ALKYLCOMPSUBST being solid, reaction was done under N2 atmosphere at 10 bar. Yield is isolated yield, in example 28 the yield was determined with 19F NMR with

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

Reference:
Patent; LONZA LTD; TAESCHLER, Christoph; BELLER, Matthias; NEUMANN, Helfried; HE, Lin; NATTE, Kishore; ELLINGER, Stefan; ZARAGOZA DOERWALD, Florencio; WO2015/185677; (2015); A1;,
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These common heterocyclic compound, 60789-54-0, name is ((4-Bromobutoxy)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. COA of Formula: C11H15BrO

. A suspension of NaH (60% in mineral oil, 440 mg, 14 mmol) in DMF [(50] ml) was slowly added to a stirred solution of benzyl-4-bromobutyl ether (3.33g, 13.7 mmol) and amide 26 (5.41 g, 5.48 mmol) (WO 00/66587) in DMF (100 ml) kept at [5C.] The reaction mixture was stirred for 10 h at [50] C, quenched with 5 ml of H20 at [0] C, and evaporated to dryness in vacuo. The residue was taken up in ethyl acetate, washed with [H20,] and purified on a silica gel column using ethyl acetate/hexane: 3/7 as eluant; [5.] [1G, (81%)] of 27 were obatained [;’H-NMR] (CDCl3) : 0.97 (t, J=7. 1 Hz, 3H), 1.2-1. 5 (m, 16H), 2.27 (s, 3H), 2.29 (s, 9H), 2.55 (s, 24H), 2.9-3. 2 (m, 16H), 3.31 (t, J=6.0 Hz), 4.41 (s, 2H), 6.9-7. 0 (m, 8H), 7.2- 7.4 (m, [5H).]

The synthetic route of ((4-Bromobutoxy)methyl)benzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SLIL BIOMEDICAL CORPORATION; WO2004/2991; (2004); A1;,
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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. 22236-08-4, name is 3-(Difluoromethoxy)aniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 22236-08-4

Intermediate 37 rac-Allyl [ 1 – {N’-cyano-N- [3 -(difluoromethoxy)phenyl] carbamimidoyl }-3-(3 ,4-dichloroph( dihydro-l/7-pyrazol-4-yl]methylcarbamate To a stirred solution of w-difluoromethoxy aniline, 10.1 g (6.35 mmol) in anhydrous tetrahydrofuran (30 mL) at -60 C under a nitrogen atmosphere was added lithium diisopropylamide, 3.2 l. (6.35 mmol, 2 M in tetrahydrofuran) . The reaction mixture was stirred for 30 min at -60 C before adding rac- phenyl 4-{[(ailyioxy)carbonyl](methyl)amino}-N-cyano-3-(3,4-dichiorophenyl)-4,5-dihydro-lH- pyrazole- 1 -carboximidate (intermediate 36) 1.0 g (2.12 mmol), in tetrahydrofuran (10 mL). The reaction mixture was stirred for 30 min at -60C and 1 h at room temperature. The reaction mixture was quenchend with water, then poured into brine and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, filtered and the solvent evaporated. The residue was purified by column chromatography on a NH- silica phase (eluent: hexane/ethyl acetate) to yield rac-allyl [1-{Nu’- cyano-N-[3-(difluoromethoxy)phenyl]carbamimidoyl}-3-(3,4-dichlorophenyl)-4,5-dihydro-lH- pyrazol-4-yl]methylcarbamate, 875 mg (77%) as a beige oil. LCMS (method 2): R, = 1.36 min MS (ESI): [M + Hf = 536.8

The synthetic route of 22236-08-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; STELLFELD, Timo; MOWAT, Jeffrey Stuart; STRESEMANN, Carlo; HILLIG, Roman; KOeHR, Silke; STOeCKIGT, Detlef; WEISKE, Joerg; HARTUNG, Ingo; BARAK, Naomi; CHRIST, Clara; TER LAAK, Antonius; BADOCK, Volker; CRAMPTON, Rosemary Helen; STEFANUTI, Ian; (194 pag.)WO2016/166186; (2016); A1;,
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2688-84-8, name is 2-Phenoxyaniline, 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. Application In Synthesis of 2-Phenoxyaniline

General procedure: The mixture of intermediate Bn-2 (1 eq.), p-toluenesulfonic acid monohydrate (PTSA*H2O) (172.5 g, 3 eq) in acetonitrile (ACN)(224 ml, 1.3 M) was cooled to 5 C. by using an ice bath. Sodium nitrite (NaNO2)(41.7 g, 2 eq.) in 240 ml water was added dropwise. After the addition was finished, the mixture was kept at 5 C. 1 hr. The resulting diazonium salt was treated slowly with potassium iodide (KI) (100 g, 2 eq.) in 300 ml water. After the completion of the reaction, the residue was extracted with EA and the combined organic layer was washed with a 10% Na2SO3(aq) and then dried over Na2SO4. The organic layer was concentrated under reduced pressure after filtration. The crude mixture was purified by silica-gel column chromatography to obtain intermediate Bn.

The synthetic route of 2688-84-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NICHEM FINE TECHNOLOGY CO., LTD.; LU, Tai-Ni; WU, Hui-Ling; SHIEH, Shwu-Ju; CHEN, Chi-Chung; (108 pag.)US2019/92745; (2019); A1;,
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Application of 2216-69-5, A common heterocyclic compound, 2216-69-5, name is 1-Methoxynaphthalene, molecular formula is C11H10O, 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: 1-Methoxy-3,5-dimethylbenzene (100mg, 0.73 mmol), N-Bromosuccinimide (NBS,260 mg,1.46 mmol) and one ball (5 mmdiameter, stainless steel) were transferred to a milling jar (10 mL, stainlesssteel). The ball-milling operation was performed and the progress of reactionwas monitored by TLC/1H NMR.[1]After completion, the reaction mixture was transferred into 30 mL ethyl acetateand cooled at 0 C. The product was isolated as filtrate upon paper filtrationand waste succinimide as precipitate. The resulting filtrate were concentrated in vacuoto isolate 250 mg (yield: 85%) of 2bas colourless powder. To test the efficiency in largescale, the reaction was also performed for the mono-bromination of1-methoxy-3,5-dimethylbenzene in 1.3 g scale for 1 h and the product wasisolated in 87% yield.[1] Themilling apparatus was stopped and small portion of the sample was collectedfrom the reaction jar to study either TLC/ proton NMR. Following, the reaction was started again andthis operation time was excluded for reporting the reaction timing.

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; Bose, Anima; Mal, Prasenjit; Tetrahedron Letters; vol. 55; 13; (2015); p. 2154 – 2156;,
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Electric Literature of 5961-59-1,Some common heterocyclic compound, 5961-59-1, name is 4-Methoxy-N-methylaniline, 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.

The synthesis of target compound 3 (Scheme 1C), started with the synthesis of a reported method for compound i.?3 2-Bromo-i,i-diethoxyethane (compound 10) was reacted with ethyl2-cyanoacetate to obtain compound 1 lwhich was cyclized to compound 12 using acetamidine hydrochloride under basic conditions. Chlorination of compound 12 using POC13 provided compound 13 in 80% yield. Displacement of the chloride of compound 13 with 4-methoxy-N- methyl aniline (compound 14) and catalytic amounts of HC1 in isopropanol, provided compound1. Methylation of compound 1 with Mel under basic conditions afforded compound 3 in 85% yield. The synthesis of target compound 5 (Scheme 1C), involved N-formylation of 4-methoxy- 2-methylanline (compound 15) to afford compound 16 in 70% yield. LAH reduction of compound 16 provided substituted aniline compound 17. Displacement of the chloride of compound 13 with anilines (compounds 15 and 17) and catalytic amounts of HC1 in isopropanol provided compounds 4 and 5 (75% and 70% respectively).

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

Reference:
Patent; DUQUESNE UNIVERSITY OF THE HOLY SPIRIT; GANGJEE, Aleem; (91 pag.)WO2016/22890; (2016); A1;,
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Synthetic Route of 41365-75-7,Some common heterocyclic compound, 41365-75-7, name is 1-Amino-3,3-diethoxypropane, molecular formula is C7H17NO2, 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 35; 3-(l-(((35,4/f)-l-(cyclopentanecarbonyl)-4-hydroxy-4-phenylpyrrolidin-3-yl)methyl)pi peridin-4-yl)-l-(4-(trifluoromethyl)benzyl)-3,4-dihydropyrimidiii-2(lH)-oneStep ACyclopentyl((3R,4S)-4-((4-(3,3-diethoxypropylamino)piperidin-l-yl)methyl)-3-hydroxy-3-p henylpyrrolidin-l-yl)methanone Following the procedure in Scheme 6, a mixture of l-(((3S,4R)-l-(cyclopentanecarbonyl) – 4-hydroxy-4-phenylpyrrolidin-3-yl)methyl)piperidin-4-one (1.0 g, 2.7 mmol), acetic acid (0.16 mL, 2.7 mmol), NaBH(OAc)3 (0.86 g, 4.05 mmol) and 3,3-diethoxypropan-l-amine (0.48 mL, 2.97 mmol) in diy THF (8 mL) was stirred at room temperature overnight. After this time, the mixture was diluted with EA and washed sequentially with NaOH, NaHCO3 and brine. The organic phase was dried over Na2SO4 and concentrated to yield crude amine which was used without further purification in the next step. MS (ESI, Pos. 1.5 kV) m/z 502.5 (M+H)+, 524.5 (M+Na)+.

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

Reference:
Patent; SHANGHAI TARGETDRUG CO., LTD.; AVEXA LIMITED; WO2009/89659; (2009); A1;,
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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. 37466-89-0, name is 3-Methoxybenzene-1,2-diamine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of 3-Methoxybenzene-1,2-diamine

Step 1: Reaction of 1,2-diamino compound (Chemical Formula 2) with oxalic acid; A 3-methoxybenzene-l,2-diamine compound (1.86 g, 13.5 mmol) represented by Chemical Formula 2-1 and oxalic acid (1.23 g, 13.6 mmol) were added to 10 mL of 3 N HCl solution. After stirring at room temperature for 10 minutes, reaction was carried out for 3 days under reflux. Then, after cooling to room temperature, the reaction mixture was filtered. The filtered compound was repeatedly washed with cold water to obtain a quinoxaline-2,3- dione compound (2.26 g, 87%) represented by Chemical Formula 3-1.1H NMR (500 MHz, DMS(Hi6) 3.86 (s, 3H), 6.75 (d, J = 8.1 Hz1 IH), 6.80 (d, J= 8.0 Hz, IH), 7.05 (t, J = 8.2 Hz, IH), 11.24 (br s, IH), 11.91 (br s, IH); n/z ( [M+l] ) 139.

The synthetic route of 37466-89-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY; AMOREPACIFIC CORPORATION; WO2009/41789; (2009); A2;,
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Some common heterocyclic compound, 111-95-5, name is Bis(2-methoxyethyl)amine, 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. Recommanded Product: Bis(2-methoxyethyl)amine

The product from step 27 1 (440 mg, 1.36 mmol) was dissolved in 7 DMF (25 mL), treated with HOBt.H2O (624 mg, 4.08 mmol), and 6 EDC.HCl (786 mg, 4.10 mmol) and stirred for 30 min at room temperature. 43 Bis(2-methoxylethyl)amine (620 mL, 559 mg, 4.20 mmol) was added and the resulting mixture was stirred at room temperature for 16 h and concentrated. The residue was partitioned with water and EtOAc. The EtOAc layer was separated and the aqueous was extracted again with EtOAc. The combined organic layers were washed with 0.5 N HCl, saturated sodium bicarbonate, and brine. The organic layer was dried (Na2SO4), filtered and concentrated to afford 214 mg of 44 3-(bis(2-methoxyethyl)amino)-6-bromo-N2,N2,N5,N5-tetrakis(2-methoxyethyl)pyrazine-2,5-dicarboxamide (26% yield) as a brown oil: LCMS (5-95% gradient acetonitrile in 0.1% TFA over 10 min), single peak retention time=3.85 min on 30 mm column, (M+H)+=608.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 111-95-5, its application will become more common.

Reference:
Patent; MediBeacon Inc.; Debreczeny, Martin P.; Rajagopalan, Raghavan; Dorshow, Richard B.; Neumann, William L.; Rogers, Thomas E.; (54 pag.)US2019/125901; (2019); A1;,
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Synthetic Route of 54314-84-0, A common heterocyclic compound, 54314-84-0, name is ((3-Bromopropoxy)methyl)benzene, molecular formula is C10H13BrO, 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.

Intermediate 104a: diethyl 2-(3-(benzyloxy)propyl)malonate To a suspension of sodium hydride (1.05 g, 26 mmol) in tetrahydrofuran (40 mL), was added diethyl malonate (7g, 44 mmol). Once evolution of gas had ceased, ((3- bromopropxy)methyl)benzene (5 g, 22 mmol) was added. The reaction mixture was heated in a 90 deg C bath for 6 h, then cooled to ambient temperature. The reaction was diluted with diethyl ether (100 mL) and washed with water (100 mL). The aqueous layer was separated and extracted with diethyl ether (2 x 100 mL). The combined organic layers were dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica-gel chromatography with ethyl acetate and heptanes as eluent to provide the desired compound. H NMR (400 MHz, CDCI3) delta 7.31-7.38 (m, 4H), 7.25-7.31 (m, 1 H), 4.50 (s, 2H), 4.10-4.27 (m, 7H), 3.50 (t, =6.3 Hz, 2H), 3.32-3.41 (m, 2H), 1.93-2.08 (m, 2H), 1.60 – 1.73 (m, 2H), 1.20- 1.38 (m, 10H) ppm.

The synthetic route of 54314-84-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; BARYZA, Jeremy Lee; BECKWITH, Rohan Eric John; BOWMAN, Keith; BYERS, Crystal; FAZAL, Tanzina; GAMBER, Gabriel Grant; LEE, Cameron Chuck-Munn; TICHKULE, Ritesh Bhanudasji; VARGEESE, Chandra; WANG, Shuangxi; WEST, Laura; ZABAWA, Thomas; ZHAO, Junping; WO2014/136086; (2014); A1;,
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