Tag: M.W=100-200

Synthetic Route of 4457-67-4, 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 4457-67-4 as follows.

Step 1. (S)-3,4-Dihydro-6-chloro-4-hydroxy-2-(4-methoxybutyl)-2H-thieno[3,2-e]-1,2-thiazine-1,1-dioxide (6, R3 =CH2 CH2 CH2 CH2 OCH3) A mixture of (S)-3,4-dihydro-6-chloro-4-hydroxy-2H-thieno[3,2-e]-1,2-thiazine-1,1-dioxide (5, 65.4 g) and potassium carbonate (113.3 g) in dimethylsulfoxide (350 mL) was treated with 1-bromo-4-methoxybutane (20.6 g) and the mixture was stirred at ambient temperature for 4 hours. Another 20.6 grams of 1-bromo-4-methoxybutane was then added and the mixture was stirred at ambient temperature for 18 hours. TLC analysis after this period indicated incomplete reaction, so another 4.6 grams of 1-bromo-4methoxybutane was added and the mixture was stirred at ambient temperature for another 3 hours. At this point, TLC indicated complete reaction. The mixture was poured into saturated aqueous sodium chloride (1 L) and extracted with diethyl ether (3*150 mL). The organic phase was washed sequentially with 100 mL each of 10percent aqueous sodium hydroxide, 1:1 5.25percent sodium hypochlorite/water, and saturated aqueous sodium chloride, dried over sodium sulfate, and stripped of solvent by rotary evaporation. Residual solvent was removed under vacuum to provide 82 grams (92percent) of (S)-3,4-dihydro-6-chloro-4-hydroxy-2-(4-methoxybutyl)-2H-thieno[3,2-e]-1,2-thiazine-1,1-dioxide as a light yellow oil: IR (film) 3500, 3350, 3070, 2950, 2850, 1525, 1480, 1440, 1380, 1330, 1160, 1120, 1080, 1020, 1100 cm-1; [alpha]25D +11.4° (c=1.1, methanol); Anal. Calcd for C11 H16 ClNO4 S2: C, 40.55; H, 4.95; N, 4.30. Found: C, 40.47; H, 4.99; N, 4.27.

According to the analysis of related databases, 4457-67-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Alcon Laboratories, Inc.; US5344929; (1994); A;,
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Synthetic Route of 870563-60-3, 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. 870563-60-3, name is (4-Fluoro-2-methoxyphenyl)methanamine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a stirred solution of ethyl 2-(l-bromo-2-ethoxy-2-oxoethyl)benzoate (Othman, M.; Decroix, B: Synth. Comm. 1996, 26, 2803) (945 mg, 3 mmol) in acetonitrile (15 mL) containing triethyl amine (835muL, 6 mmol) a solution of 4-fluoro-2-methoxybenzylamine (698 mg, 4.5 mmol) in acetonitrile (1 mL) was added dropwise under argon at O0C. The reaction, mixture was stirred at ambient temperature for 2 h. The mixture was diluted with ethyl acetate (50 mL), washed with water and brine. The organic phase was dried over magnesium sulfate and concentrated in vacuum. The residue was purified by column chromatography on silica gel using heptane/ethyl acetate (3:2) as an eluent to yield ethyl 2- (4-fluoro-2-methoxybenzyl)-3-oxoisoindoline-l-carboxylate as yellowish oil (857 mg, o/o).IH NMR (400 MHz, CDCl3) delta ppm 7.84 – 7.88 (m, 1 H), 7.67 – 7.76 (m, 1 H), 7.59 – 7.65 (m, 1 H), 7.46 – 7.58 (m, 2 H), 7.28 – 7.33 (m, 1 H)5 6.58 – 6.66 (m, 1 H), 5.21 (d, 1 H), 4.96 (s, 1 H), 4.47 (d, 1 H), 4.17 – 4.38 (m, 2 H), 3.82 (s, 3 H), 1.32 (q, 3 H) MS (ESI) m/z 344 [M+H], MS (ESI) m/z 342 [M-H]

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, (4-Fluoro-2-methoxyphenyl)methanamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASTRAZENECA AB; WO2008/8020; (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 151414-47-0 as follows. Formula: C7H7F2NO

To a solution of 164 mg (0.372 mmol [calculation value with the purity defined as 100%]) of ethyl 5-(chioro- carbonyl)-6,6-dimethyl-3-[1 -(trimethylsilyl)cyclobutanecarboxamido]-5,6-dihydropyrrolo[3,4-c]pyrazole-2(4H)- carboxylate synthesized in the same way as in Reference Example 4 in 1.5 ml of 1,4-dioxane, 0.33 ml (1.9 mmol) of DIPEA and 516 mg (3.24 mmol) of 2,6-difluoro-4- methoxyaniline were added at room temperature in a nitrogen atmosphere and reacted at 1000 C. for 9.5 hours with stirring. Subsequently, the reaction solution was cooled to room temperature, and 0.20 ml (1.8 mmol) of N,N-dimethylethane- 1 ,2-diamine was added thereto at room temperature and then reacted at room temperature for 4 hours with stirring.10748] After completion of the reaction, ethyl acetate was added to the reaction solution, followed by washing with a 5% aqueous potassium bisulfate solution. Afier separation into an organic layer and an aqueous layer, the aqueous layer was subjected to extraction twice with ethyl acetate. The whole organic layer thus obtained was dried over anhydrous magnesium sulfate, then filtered, and concentrated under reduced pressure. The obtained concentration residue was subjected to preparative column chromatography (apparatus 1, DIOL silica gel, elution solvent: n-hexane:ethyl acetate=75:25-60:40-M5:55 (V/V)), and a fraction containing the compound of interest was concentrated under reduced pressure. The obtained concentration residue was subjected to preparative column chromatography (apparatus 1, silica gel, elution solvent: 1 ,2-dichloroethane:metha- nol=99:1-98:2-95:5 (V/V)), and a fraction containing the compound of interest was concentrated under reduced pressure. The obtained concentration residue was dissolved in ethyl acetate, then n-hexane was added thereto, and the deposited solid was collected by filtration, washed with n-hexane, and then dried under reduced pressure to obtain 105 mg of the title compound (yield: 57% [calculation value with the purity of the starting material defined as 100%]) as a white solid.10749] Mass spectrum (CI, mlz): 492 [M+1].10750] ?H-NMR spectrum (400 MHz, DMSO-d5) oe: 12.26 & 11.72 (br s, total 1H), 9.59 (s, 1H), 7.80-7.59 (m, 1H), 6.79-6.69 (m, 2H), 4.64-4.47 (m, 2H), 3.77 (s, 3H), 2.56-2.40 (m, 2H), 2.28-2.11 (m, 2H), 1.92-1.71 (m, 2H), 1.69-1.53 (m, 6H), 0.13-0.05 (m, 9H).

According to the analysis of related databases, 151414-47-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; UBE INDUSTRIES, LTD.; IWASE, Noriaki; AGA, Yasuhiro; USHIYAMA, Shigeru; KONO, Shigeyuki; SUNAMOTO, Hidetoshi; MATSUSHITA, Takashi; OGI, Sayaka; UMEZAKI, Satoshi; KOJIMA, Masahiro; ONUMA, Kazuhiro; SHIRAISHI, Yusuke; OKUDO, Makoto; KIMURA, Tomio; (165 pag.)US2018/186818; (2018); A1;,
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Electric Literature of 6850-60-8,Some common heterocyclic compound, 6850-60-8, name is (4-Ethoxyphenyl)methanamine, molecular formula is C9H13NO, 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: Synthesis of (2R, 3R, 4S, 5R)-2-(6-(benzylamino)-9H-purin-9-yl)-5-(hydroxymethyl) tetrahydrofuran-3,4-diol, 2. In a 7 mL MW vessel, 6-chloropurinoriboside 3 (20 mg, 0.07 mmol), benzylamine 4 (7.5 mg,0.07 mmol, 7.7 muL) and triethylamine (7.08 mg, 0.07 mmol, 9.8 muL)were mixed. The solid mixture was stirred in CEM Explorer. MWMethod: T = 210 C, Power: 300 W, Hold Time: 1 min, P = 250 PSI,Power Max activated. After cooling, the solvent was removed in vacuoand the crude was dissolved in methanol and then purified on PTLC(DCM/MeOH 9:1) to afford compound 2 as white solid (24 mg, 94%).C17H20N5O4: 358.1510; Found 358.1515. Rt: 8.92 min.

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

Reference:
Article; Grimaldi, Manuela; Randino, Rosario; Ciaglia, Elena; Scrima, Mario; Buonocore, Michela; Stillitano, Ilaria; Abate, Mario; Covelli, Verdiana; Tosco, Alessandra; Gazzerro, Patrizia; Bifulco, Maurizio; Rodriquez, Manuela; D’Ursi, Anna Maria; Bioorganic Chemistry; vol. 98; (2020);,
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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. 10075-63-5, name is 1,5-Dimethoxynaphthalene, A new synthetic method of this compound is introduced below., Quality Control of 1,5-Dimethoxynaphthalene

General procedure: To a flask containing 1,3,5-trimethoxybenzene (1009.1 mg, 6 mmol) were added POCl3 (1011.9 mg, 6.6 mmol) and DMF (1754.1 mg, 24 mmol) at 0 C. After being stirred for 3 h at 40 C, DIH (2279.5 mg, 6 mmol) and aq ammonia (12 mL, 28-30%) were added to the reaction mixture. The obtained mixture was stirred for 3 h at rt. After the reaction, the mixture was poured into aq satd Na2SO3 solution and extracted with CHCl3 (3×20 mL). The organic layer was dried over Na2SO4, filtered, and evaporated to provide almost pure 2,4,6-trimethoxybenzonitrile (1156.1 mg) in 99% yield.

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; Ushijima, Sousuke; Moriyama, Katsuhiko; Togo, Hideo; Tetrahedron; vol. 68; 24; (2012); p. 4588 – 4595;,
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Synthetic Route of 50868-72-9, 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. 50868-72-9, name is 5-Methoxy-2-methylaniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Step 1: 3-Bromo-4-methylanisole To a suspension of 5-methoxy-2-methylanilme (5.00 g, 36.4 mmol) in water (144 mL) at 10 0C, was added cone H2SO4 (56 mL), while maintaining internal temperature below 25 0C. After 1 h at rt, the mixture was cooled to 3 0C and a solution of sodium nitrite (3.77 g, 54.7 mmol) in water (20 mL) was added dropwise over 30 mm, keeping the internal temperature below 5 0C After 1 h at 3 0C, the yellow heterogeneous mixture was poured into a 5 0C solution of CuBr (52.0 g, 364 mmol) in 48% aqueous HBr (260 mL). The dark mixture was heated at 60 0C for 2 h, allowed to cool to rt and extracted with Et2O (3x) (solid Na2S2O3 was added in the extraction process for partial decoloration). The combined organics were washed with 1 N NaOH (3x), 10% aq. Na2S2O3 and brine, dried (Na2SO4) and concentrated, affording the title compound as an orange liquid which was used without further purification in the next Step. 1H NMR (500 MHz, acetone-d6): delta 7.24 (d, IH), 7.14 (d, IH), 6.87 (dd, IH), 3.80 (s, 3H), 2.31 (s, 3H).

The synthetic route of 5-Methoxy-2-methylaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK FROSST CANADA LTD.; WO2006/99735; (2006); A1;,
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Synthetic Route of 151414-47-0,Some common heterocyclic compound, 151414-47-0, name is 2,6-Difluoro-4-methoxyaniline, molecular formula is C7H7F2NO, 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 mixture of 2,6-difluoro-4-methoxybenzenamine (0.98 g, 6.9 mmol) in toluene (20 mL) was added 6-chloro-3-pyridinecarboxaldehyde (1.0 g, 6.3 mmol). The reaction mixture was heated at reflux with the use of a Dean-Stark trap for azeotropic removal of water. After 16 h the reaction mixture was cooled to room temperature and concentrated under reduced pressure. The resulting material was dried in a vacuum oven at 55 C overnight to provide the title compound as a light brown solid (1.66 g).in NMR (CDCI3) delta 8.74 (s, 1H), 8.73 (d, J = 2.44 Hz, 1H), 8.32 (dd, J = 2.20 Hz, J= 8.29 Hz, 1H), 7.44 (d, J= 8.29 Hz, 1H), 6.59-6.52 (m, 2H), 3.82 (s, 3H)..9F NMR (CDCI3) delta -121.48 to -121.40 (m, 2F).

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-4-methoxyaniline, its application will become more common.

Reference:
Patent; E. I. DU PONT DE NEMOURS AND COMPANY; GREGORY, Vann; TAGGI, Andrew, Edmund; WO2011/56463; (2011); A2;,
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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. 131713-50-3, name is 2,2-Dimethoxypropan-1-amine, A new synthetic method of this compound is introduced below., SDS of cas: 131713-50-3

Step 1 A solution of Cbz-D-Valine (500 g, 1.99 mol) and N-methylmorpholine (201.8 g, 1.99 mol) in anhydrous THF (8 L) was cooled to -15 C., i-butylchlorofomate (299 g, 2.19 mol) was added dropwise under stirring. After 30 min, a solution of 1-amino-2,2-dimethoxypropane (209.5 g, 1.99 mol) in THF (1 L) was added slowly and the temperature was maintained at -15 C. for 2 h. The reaction mixture was washed with brine (2 L) and the organic phase was concentrated to remove the THF. The residue was diluted with EtOAc (4 L), washed with 1N aqueous HCl (2*2 L), washed with sat. NaHCO3 (2 L) and Na2CO3 (2 L), and washed with brine (1.5 L). After drying over Na2SO4, the organic solvent was removed under reduce pressure to afford (R)-benzyl (1-((2,2-dimethoxyethyl)amino)-3-methyl-1-oxobutan-2-yl)carbamate as a white solid (670 g, yield 99.5%), which was used for next step without further purification. LC-MS m/z 360.9 [M+Na]+. 1H NMR (CD3OD 300 MHz): delta 7.35-7.30 (m, 5H), 5.08 (s, 2H), 4.45-4.35 (m, 1H), 3.95-3.85 (m, 1H), 3.34-3.25 (m, 8H), 2.10-1.90 (m, 1H), 0.94-0.91 (m, 6H).

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; Vitae Pharmaceuticals, Inc.; Gregg, Richard E.; US2015/250787; (2015); 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. 1187160-18-4, name is 7-Methoxy-2,3-dihydro-1H-inden-1-amine hydrochloride belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of 7-Methoxy-2,3-dihydro-1H-inden-1-amine hydrochloride

Step A: Rac-7-methoxy-indan-1-ylamine hydrochloride (2.20 g, 0.01 1 mmol) was dissolved in acetic acid (100 mL). After cooling to 0 C. sulfuryl chloride (1.88 mL, 0.23 mmol) was slowly added and the reaction mixture was stirred for 16 h at ambient temperature. Then the solvent was evaporated and the residue was taken up in isopropanol. Thereby a precipitate formed which was isolated and dried on high vacuum to yield rac-4,6-dichloro-7-methoxy-indan-1-ylamine (2.0 g, 68%) as a white solid; MS: m/e=269.6 (M+H+).

The synthetic route of 1187160-18-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kolczewski, Sabine; Riemer, Claus; Roche, Olivier; Steward, Lucinda; Wichmann, Juergen; Woltering, Thomas; US2009/227570; (2009); A1;,
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These common heterocyclic compound, 127657-97-0, name is Benzyloxyacetaldehyde dimethyl acetal, 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. Computed Properties of C11H16O3

L-Ascorbic acid (44.9 g, 0.255 mol) was added to a solution of compound Tr-1 (60 g, 0.306 mol) in dry acetonitrile (898 mL) followed by addition of pTSA monohydrate (15.5 g, 0.076 mol) and the reaction mixture was heated at 90 C for 1 h. After completion of the reaction (TLC), half the volume of the acetonitrile was distilled off and the process was repeated twice. Solvent was removed completely and the title compound as a mixture of stereoisomers was obtained (91 g). The product was directly taken to the next step without further purification.

The synthetic route of Benzyloxyacetaldehyde dimethyl acetal has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MEDIVIR AB; BETHEL, Richard; ENEROTH, Anders; KLASSON, Bjoern; OeBERG, Fredrik; (73 pag.)WO2016/30335; (2016); A1;,
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