Month: March 2021

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. 701-07-5, name is 2-(2′-Bromophenoxy)propane, A new synthetic method of this compound is introduced below., Quality Control of 2-(2′-Bromophenoxy)propane

A mixture of 14 (0.114 g, 0.53 mmol), 19 (0.171 g, 0.79 mmol), PdCl2(PPh3)2 (0.037 g, 0.053 mmol) and TBAF (IM in THF) (2.65 mL, 2.65 mmol) were suspended in anhydrous THF (1 mL) and microwaved at 140 0C for 15 min. The reaction mixture was cooled to room temperature and diluted with DCM (30 mL). The mixture was filtered and concentrated in vacuo. The crude product was purified by HPLC to afford the title compound (0.09 g, 6%).[0209] 1H NMR (500 MHz, DMSO-J6): delta 1.37 (d, J = 6.1 Hz, 6H), 4.75-4.80 (m, IH), 6.67 (d, J = 3.5 Hz, IH), 7.01 (t, J = 7.4 Hz, IH), 7.17 (d, J = 8.4 Hz, IH), 7.44-7.47 (m, IH), 7.61- 7.63 (m, IH), 7.69 (d, J = 3.5 Hz, IH ), 8.75 (s, IH), 12.3 (s, IH)[0210] MS (ES+): m/z 278 (M+H)+

The synthetic route of 701-07-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TARGEGEN INC.; WO2009/55674; (2009); A1;,
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Synthetic Route of 658-89-9,Some common heterocyclic compound, 658-89-9, name is 4-(Trifluoromethoxy)benzene-1,2-diamine, molecular formula is C7H7F3N2O, 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 stirred solution of N-boc-O-methyl-L-threonine (1.99 g, 8.53 mmol) in acetonitrile (27 ml) at 0C was added N-methylmorpholine (1.3 ml, 12.0 mmol) followed by the dropwise addition of isobutyl chloroformate (1.3 ml, 10 mmol). The reaction mixture was stirred at 0C for 45 minutes. 4-(Trifluoromethoxy)benzene-1,2-diamine (1.64 g, 8.53 mmol) was dissolved in acetonitrile (14 mL) and cooled to 0C. To this was added the solution of the activated N-Boc-O-methyl-L-threonine via a dropping funnel fitted with a cotton wool plug. After the addition was complete the dropping funnel and cotton wool plug was rinsed with acetonitrile (10 mL) and was stirred at room temperature overnight. The reaction concentrated in vacuo, then diluted with EtOAc (80 mL) and citric acid (40 mL, 5% aqueous solution) was added. The organics were separated, washed with citric acid (40 mL, 5% aqueous solution), followed by brine (20 mL), dried over sodium sulphate and reduced in volume to afford an orange solid (3.69 g) which was used without further purification (mix of regioisomers). tert-Butyl ((1R,2R)-2-methoxy-1-(6-(trifluoromethoxy)-1H-benzo[d]imidazol-2-yl)propyl)carbamate. A mixture of tert-butyl ((2S,3R)-1-((2-amino-4-(trifluoromethoxy)phenyl)amino)-3-methoxy-1-oxobutan-2-yl)carbamate and tert-butyl ((2S,3R)-1-((2-amino-5-(trifluoromethoxy)phenyl)amino)-3-methoxy-1-oxobutan-2-yl)carbamate (3.48 g, 8.54 mmol) was diluted with acetic acid (33 ml) and stirred at room temperature for 4.5 days. The reaction was quenched by slow addition of a K2CO3 solution (10% aqueous solution, 50 ml) and EtOAc (50 ml) was added. The organics were separated, combined and washed with brine (20 mL), dried over Na2SO4 and concentrated in vacuo to afford a dark brown gum which was purified by column chromatography (120g ISCO column, 0-30% EtOAc/heptane) to obtain 1.64 g (49%) of the title compound as a solid. This was taken on to next step without further purification. 1H NMR (400 MHz, DMSO-d6) delta 12.43 (br. s., 1H), 7.54 (br. s., 2H), 7.13 (br. s., 1H), 7.02 (d, J=7.81 Hz, 1H), 4.83 (dd, J=4.98, 8.10 Hz, 1H), 3.72-3.85 (m, 1H), 3.21 (s, 3H), 1.38 (s, 9H), 1.02 (d, J=6.25 Hz, 3H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-(Trifluoromethoxy)benzene-1,2-diamine, its application will become more common.

Reference:
Article; Brown, Alan D.; Bagal, Sharan K.; Blackwell, Paul; Blakemore, David C.; Brown, Bruce; Bungay, Peter J.; Corless, Martin; Crawforth, James; Fengas, David; Fenwick, David R.; Gray, Victoria; Kemp, Mark; Klute, Wolfgang; Malet Sanz, Laia; Miller, Duncan; Murata, Yoshihisa; Payne, C. Elizabeth; Skerratt, Sarah; Stevens, Edward B.; Warmus, Joseph S.; Bioorganic and Medicinal Chemistry; vol. 27; 1; (2019); p. 230 – 239;,
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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. 1663-61-2, name is (Triethoxymethyl)benzene, A new synthetic method of this compound is introduced below., name: (Triethoxymethyl)benzene

General procedure: The starting hydrazide 5a,b (10.0 mmol) was added to a mixture of the triethyl orthoester (15.0 mmol) and glacial AcOH (10 mL). The mixture was kept under reflux until the starting hydrazide was fully consumed (monitored by TLC, 1?4 h). After cooling, the excess orthoester and AcOH were evaporated under reduced pressure. The crude product 7a?f was subjected to silica gel column chromatography (benzene?EtOAc, 1:3) or was crystallised (benzene?hexanemixtures).

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; Kudelko, Agnieszka; Jasiak, Karolina; Synthesis; vol. 45; 14; (2013); p. 1950 – 1954;,
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Related Products of 701-07-5,Some common heterocyclic compound, 701-07-5, name is 2-(2′-Bromophenoxy)propane, molecular formula is C9H11BrO, 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 33:[0161] A well-dried flask was first charged with l-bromo-2-isopropoxybenzene (500 mg, 2.32 mmol) and 1,4-diazepane (348 mg, 3.48 mmol), which was evacuated and backfilled with N2 through a balloon under gentle warming (40C). Toluene was charged and the mixture was bubbled with N2 for 10 min, then BINAP (44 mg, 0.07 mmol) and Pd2dba3 (14 mg, 0.02 mmol) were added to the mixture. After the addition of DBU (0.5 mL), the solution was warmed at 60- 70C while a fine powder of iBuONa (334 mg, 3.48 mmol) was added in one portion to start the amination. After the reaction mixture cooled to rt, (Boc)20 (1.265 g, 5.8 mmol) was dissolved in DCM and added dropwise to the reaction mixture then stirred for 3 h at rt. The reaction mixture was diluted with water and extracted with EtOAc. The combined EtOAc layers were washed with brine, dried over anhydrous Na2S04, concentrated in vacuo and purified by flash chromatography on silica gel column (elution with PE/EtOAc = 30:1) to give tert-butyl 4-(2-isopropoxyphenyl)- 1,4-diazepane-l-carboxylate (intermediate 33) (172 mg, 22%).

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′-Bromophenoxy)propane, its application will become more common.

Reference:
Patent; THE UNIVERSITY OF NORTH CAROLINA AT CHAPEL HILL; JIN, Jian; ROTH, Bryan; FRYE, Stephen; WO2012/3418; (2012); A2;,
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Related Products of 35822-58-3,Some common heterocyclic compound, 35822-58-3, name is 2-Bromobenzaldehyde diethyl acetal, molecular formula is C11H15BrO2, 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: In a 200 mL three necked flask equipped with a dropping funnel, a THF solution of S2 (1.0 equiv.)was slowly added to a mixture of Mg (1.1 equiv., pre-activated by stirring for several hours in vacuo)and THF. A THF solution of alkyne (1.1 equiv.) was subsequently added, and the reaction mixturewas stirred at room temperature. Then, HCl aq. (1M) was added, and the resultant solution wasextracted with Et2O. The organic layer was washed with Brine, dried over anhydrous Na2SO4,filtered, and concentrated in vacuo to yield a crude product including S3. If needed, the purificationwas performed by a column chromatography on a silica gel (eluted with 510% EtOAc/hexane).

The synthetic route of 35822-58-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Hoshimoto, Yoichi; Kumar, Ravindra; Nishimura, Chika; Ogoshi, Sensuke; Sasaoka, Yukari; Bulletin of the Chemical Society of Japan; vol. 93; 2; (2020); p. 182 – 186;,
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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. 27191-09-9, name is 3-Methoxyaniline hydrochloride, A new synthetic method of this compound is introduced below., SDS of cas: 27191-09-9

General procedure: To a solution of compound 27 (1 mmol) in 20 mL dried CH2Cl2 was added oxalyl chloride (4 mmol). The mixture was stirred at room temperature for 24 h under argon and then concentrated to dryness under reduced pressure. Hexane (3 * 10 mL) was added to the residue, then concentrated under vacuum to dryness. To a dried CH2Cl2 (20 mL) solution of aniline hydrochloride, 4-methoxyaniline hydrochloride, 4-(trifluoromethoxy)aniline hydrochloride, 4-fluoroaniline hydrochloride, 4-chloroaniline hydrochloride, 4-bromoaniline hydrochloride, 3-methoxyaniline hydrochloride, 3-chloroaniline hydrochloride, 2-methoxyaniline hydrochloride, 2-chloroaniline hydrochloride, benzylamine hydrochloride, 4-methoxybenzylamine hydrochloride, N,N-Dimethylethylenediamine, or pyrrolidine (1.5 mmol) was added to the above acid chloride in the presence of triethylamine (3.0 mmol). The reaction mixture was stirred at room temperature for 3 h under argon and then concentrated. The obtained residue was dissolved in 2:1 MeOH/CH2Cl2 (15 mL) and then NaOMe was added until pH = 10. After stirred at r.t. for 12 h, the solution was neutralized with Dowex 50 * 8 (H+) resin until pH = 7, filtered and concentrated under vacuum. Then the residue was purified by silica gel column chromatography (CH2Cl2-MeOH, 6:1) to give compounds 4-18, respectively.

The synthetic route of 27191-09-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Liao, Yixian; Chen, Lizhu; Li, Sumei; Cui, Zi-ning; Lei, Zhiwei; Li, Hui; Liu, Shuwen; Song, Gaopeng; Bioorganic and Medicinal Chemistry; vol. 27; 18; (2019); p. 4048 – 4058;,
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Synthetic Route of 22094-18-4,Some common heterocyclic compound, 22094-18-4, name is 1,3-Dibromo-2,2-dimethoxypropane, molecular formula is C5H10Br2O2, 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 2-(2,5-difluoro-4-methylphenyl)acetonitrile (16.7 g, 100 mmol) in DMSO (200 mL) was added NaH (8 g, 200 mmol, 60% oil dispersion), portion-wise, at RT. The reaction was stirred for 1 h at RT, and then 1,3-dibromo-2,2-dimethoxypropane (39.3 g, 150 mmol) was added. The mixture was heated at 60 C for 6 h. The reaction was quenched with water (100 mL) at 0 C and extracted with EtOAc (2 x 100 mL). The organic extracts werecombined and washed with brine (2 x 50 mL), dried over Na2504, filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography using petroleumn ether/EtOAc (4/1) as eluting solvents to afford the title compound as a yellow solid (12 g, 45% yield). ?H NMR(400 MHz, DMSO-d6)oe 7.36-7.28(m, 2H), 3.18(s, 3H), 3.05(s, 3H), 3.03 (d, J= 13.6 Hz, 2H), 2.77 (d, J= 13.6 Hz, 2H), 2.24 (d, J= 1.6 Hz, 3H). LCMS (ESI): mlz = 268.0[M+Hj.

The synthetic route of 22094-18-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; RENE, Olivier; FAUBER, Benjamin; VESEY, David; WINSHIP, Paul; LADDUWAHETTY, Tammy; (97 pag.)WO2017/5668; (2017); A1;,
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145903-31-7, name is 7-Methoxy-2,3,4,5-tetrahydrobenzo[f][1,4]thiazepine, 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. Safety of 7-Methoxy-2,3,4,5-tetrahydrobenzo[f][1,4]thiazepine

As Scheme 4 demonstrates, sulfuryl chloride (15.0 mg; 0.111 mM) and Et3N (28.0 mg; 0.22 mM) were added to 7-methoxy-2,3,4,5-tetrahydro-1,4-benzothiazepine (1) (19.4 mg; 0.1 mM) in CH2Cl2 (20 ml), at 0 C. After stirring the mixture for 2 h at 0 C., 1-piperonylpiperazine (27 mg; 0.12 mM) was added. The mixture was stirred for another 2 h, and then washed with H2O and a saturated NaHCO3 solution. The excess amine was removed by addition of a base scavenger (3-(2-succinic anhydride)propylfunctionalized silica gel, 0.2 g). The yield from this synthesis was 36 mg, or 77%.

The synthetic route of 145903-31-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Marks, Andrew R.; Landry, Donald W.; Deng, Shi Xian; Cheng, Zhen Zhuang; US2005/215540; (2005); A1;,
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Reference of 458-52-6, 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. 458-52-6, name is 2-Fluoro-4-methoxyaniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A mixture of 2,4-dichloro-5-chloromethyl-pyrimidine (3.70 g, 18.7 mmol) (from Example 1b supra), 2-fluoro-4-methoxy-phenylamine (2.40 g, 17.0 mmol) (from Example 14a supra) and potassium carbonate (4.70 g, 34.0 mmol) in acetone (100 ML) was stirred at room temperature for 18 hours.The precipitate was filtered off and the solution was concentrated under reduced pressure.The residue was diluted with ethyl acetate and washed with water and brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure.This residue was purified by flash chromatography eluding with ethyl acetate-hexanes (1:4) to give [(2,4-dichloropyrimidin-5-yl)methyl]-(4-methoxyphenyl)-amine. (Yield 3.99 g, 78percent).

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

Reference:
Patent; Chen, Yi; Dermatakis, Apostolos; Liu, Jin-Jun; Luk, Kin-Chun; Michoud, Christophe; Rossman, Pamela Loreen; US2004/204427; (2004); 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. 102-52-3, name is 1,1,3,3-Tetramethoxypropane, This compound has unique chemical properties. The synthetic route is as follows., category: ethers-buliding-blocks

EXAMPLE 53 4,5,6,7-Tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxylic acid, ethyl ester A stirred mixture of 10.88 g of 5-amino-4-pyrazolecarboxylic acid, ethyl ester, 11.51 g of malonaldehyde bis(dimethyl acetal) and 100 ml of glacial acetic acid was heated at reflux for 16 hours, then worked up as described in Example 50 to give 7.8 g of pyrazolo[1,5-a]pyrimidine-3-carboxylic acid, ethyl ester.

According to the analysis of related databases, 102-52-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; American Cyanamid Company; US4847256; (1989); A;,
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