Tag: M.W=200-300

These common heterocyclic compound, 106984-09-2, name is tert-Butyl (2-(2-(2-(2-hydroxyethoxy)ethoxy)ethoxy)ethyl)carbamate, 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. 106984-09-2

To a stirred solution of tert-butyl (2-(2-(2-(2-hydroxyethoxy)ethoxy)ethoxy)ethyl)carbamate (0.38 g, 1.29 mmol) and 2-bromoacetic acid (0.54 g, 3.8 mmol) in toluene:THF (1:1, 4 mL) was added NaOH (0.31 g, 7.7 mmol) at 45 C. The resulting reaction mixture stirred at 45 C. for 16 h. The reaction mixture was then evaporated, water (10 mL) was added and aqueous layer was acidified with 1 N HCl solution. The resulting mixture was extracted using DCM (3¡Á50 mL) and the combined organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was evaporated under reduced pressure to give 2,2-dimethyl-4-oxo-3,8,11,14,17-pentaoxa-5-azanonadecan-19-oic acid as a colorless oil (0.24 g, 53%). LC-MS (ESI+) m/z 351.4 (M+H)+.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 106984-09-2.

Reference:
Patent; Kymera Therapeutics, Inc.; Mainolfi, Nello; Ji, Nan; Kluge, Arthur F.; Weiss, Matthew M.; Zhang, Yi; (1443 pag.)US2019/192668; (2019); A1;,
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144-80-9, 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. 144-80-9, name is N-((4-Aminophenyl)sulfonyl)acetamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A solution of 0.01 mol of methyl 4-(4-bromophenyl)-2,4-dioxobutanoate in 10 mL of glacial acetic acid was added to a solution of 0.01 mol of N-(4-aminobenzenesulfonyl)acetamide and 0.01 mol of benzaldehyde in 15 mL of glacial acetic acid. The mixture was refluxed for 3-5 min and cooled, and the precipitate was filtered off and recrystallized from dioxane [8]. Yield 4.33 g (78%).

The synthetic route of N-((4-Aminophenyl)sulfonyl)acetamide has been constantly updated, and we look forward to future research findings.

Reference:
Article; Bobrovskaya; Gein; Seliverstov; Chashchina; Dmitriev; Russian Journal of General Chemistry; vol. 87; 12; (2017); p. 2776 – 2782; Zh. Obshch. Khim.; vol. 87; 12; (2017); p. 1957 – 1964,8;,
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116091-63-5, Adding a certain compound to certain chemical reactions, such as: 116091-63-5, name is 2-Methoxy-5-(2-oxopropyl)benzenesulfonamide, belongs to amides-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 116091-63-5.

a) 2-Methoxy-5-(2-oxopropyl)-benzene sulfonamide (37.3 gm, 153.3 mmol), 2-(2-ethoxyphenoxy)-1-ethanamine (29.8 gm, 164.4 mmol) and methanol (250 mL) were taken into a one liter stainless steel flask and mixed well. Catalyst Raney nickel (8 gm) was added to the flask and the mixture hydrogenated at 50 C. at hydrogen pressure of 40 psi for 30 hrs. The catalyst was removed by filtration and solvent from the filtrate was distilled off completely at 50 C. under vacuum. The dark brown crude obtained was treated with methanolic hydrochloric acid (175 mL) at 0-5 C. under stirring. Tamsulosin hydrochloride formed as a solid was filtered, washed with ethyl acetate (200 mL), suspended in methanol (120 mL) and the methanol slurry filtered to obtain off white solid material. It was dried for 3 hrs at 80 C. to give racemic tamsulosin hydrochloride. Melting point 255-257 C., chemical purity of 98.8 area % (by HPLC) and R,S ratio of 51.45:48.55 (by chiral HPLC).

According to the analysis of related databases, 116091-63-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; DIVI’S LABORATORIES LIMITED; US2006/79714; (2006); A1;,
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239074-29-4, 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 239074-29-4 as follows.

To a solution of tert-butyl (trans-4-(hydroxymethyl)cyclohexyl)carbamate (0.84 g, 3.65 mmol) in THF (15 mL) was added No.23 triphenylphosphine (1.43 g, 5.45 mmol) and No.23 4,6-dichloropyrimidin-5-ol (0.68 g, 3.65 mmol). To the mixture was added No.23 diisopropylazodicarboxylate (1.47 g, 7.27 mmol) at 0C., the mixture was stirred at room temperature for 18 hr. The reaction mixture was concentrated in vacuo and the residue was purified by column chromatography on silica gel (hexane:ethyl acetate=40:1 as eluent) to afford the tert-butyl (trans-4-(((4,6-dichloropyrimidin-5-yl)oxy)methyl)cyclohexyl)carbamate as colorless oil (0.45 g, 33% yield). LC/MS APCI: Calculated 375.11; Observed m/z [M-99 (boc)]+ 276.1. 1H-NMR 400 MHz, DMSO-d6: delta 8.68 (s, 1H), 6.75 (d, J=7.60 Hz, 1H), 3.94 (d, J=6.00 Hz, 2H), 3.16-3.14 (m, 1H), 1.89-1.79 (m, 4H), 1.73-1.71 (m, 1H), 1.38 (s, 9H), 1.19-1.16 (m, 4H).

According to the analysis of related databases, 239074-29-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Arrien Pharmaceuticals LLC; Vankayalapati, Hariprasad; US2020/131154; (2020); A1;,
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These common heterocyclic compound, 239074-29-4, name is tert-Butyl (trans-4-(hydroxymethyl)cyclohexyl)carbamate, 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. 239074-29-4

To a mixture of 7-fluoro-8-hydroxy-l-methyl-2(lH)-quinoxalinone (150 mg), 1,1- dimethylethyl [tralpha/?5-4-(hydroxymethyl)cyclohexyl] carbamate (142 mg, 0.618 mmol, for a preparation see Example l(g)) and triphenylphosphine (195 mg, 0.742 mmol) in THF (10 mL) was added DIAD (0.144 mL, 0.742 mmol) and the mixture was stirred at rt for 1 h then triphenylphosphine (195 mg, 0.742 mmol) and DIAD (0.144 mL, 0.742 mmol) were added and the reaction was stirred at rt overnight. The solvent was evaporated and the residue was purified using silica chromatography (0-20%CH3CN/DCM) to afford the title compound (272 mg) which was used in the next step without further purification. MS (ES+) m/z 423 [MNH4+].

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 239074-29-4.

Reference:
Patent; GLAXO GROUP LIMITED; JONES, Graham, Elgin; MARKWELL, Roger, Edward; HENNESSY, Alan Joseph; MILES, Timothy; PEARSON, Neil David; WO2010/45987; (2010); A1;,
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749927-69-3, The chemical industry reduces the impact on the environment during synthesis 749927-69-3, name is 4-Bromo-2-fluoro-N-methylbenzamide, I believe this compound will play a more active role in future production and life.

The bromobenzamide A-2 (10 g, 43.1 mmol), aminoisobutyric acid B-l (6.7 g, 64.6 mmol, 1.5 equiv), K2C03 (15 g, 2.5 equiv), 99% CuCl (0.8 g, 8.1 mmol, 0.2 equiv), DMF (60 mL, 6 vol) and water (1.8 mL) were added to the flask and the reaction slurry was heated to 30 C. 2-Acetylcyclohexanone (1.14 mL, 8.1 mmol, 0.2 equiv) was added to the reaction slurry followed by stirring at 105 C under nitrogen for 12-14 h. HPLC analysis showed 96.6% conversion to the desired product. The reaction mixture was then cooled to RT and extracted with water (120 mL) and IP Ac (60 mL). The lower aqueous layer was re-extracted with IP Ac (60 mL) and acidified with 180 mL of 1M citric acid to a pH of 4.0. The product began to crystallize at RT and the batch was further cooled to 5-7 C, filtered, washed with water (40 mL) and dried under vacuum at 50 C for 12 h. The reaction yielded 8.3 g of product C-1 (75.4% yield) as a tan solid with HPLC purity of 99.6%.

The chemical industry reduces the impact on the environment during synthesis 4-Bromo-2-fluoro-N-methylbenzamide. I believe this compound will play a more active role in future production and life.

Reference:
Patent; MEDIVATION PROSTATE THERAPEUTICS, INC.; JAIN, Rajendra, Parasmal; ANGELAUD, Remy; THOMPSON, Andrew; LAMBERSON, Carol; GREENFIELD, Scott; WO2011/106570; (2011); A1;,
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A common heterocyclic compound, 108468-00-4, name is 1-(N-Boc-aminomethyl)-4-(aminomethyl)benzene, molecular formula is C13H20N2O2, 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. 108468-00-4.

General procedure: A solution of 4-(Boc-aminomethyl)benzylamine (3) (1.0 mmol) and TEA (3.0 mmol) in anhydrous DCM (8 mL) was cooled with an ice bath, then the corresponding sulfochloride (1.1 mmol, dissolved in 2 mL anhydrous DCM) was added dropwise. The reaction mixture was allowed to stir at 0 C for 1 h. After removing the cooling bath, the resulting mixture was stirred for 5 h at room temperature, then diluted with saturated aqueous NaHCO3 and extracted with DCM (10 mL) for three times. The combined organic layer was sequentially washed with water and brine, dried with anhydrous Na2SO4, and concentrated in vacuo. The crude was purified by column chromatography with DCM/methanol (150:1, v/v) to give the product as a white solid.

The synthetic route of 1-(N-Boc-aminomethyl)-4-(aminomethyl)benzene has been constantly updated, and we look forward to future research findings.

Reference:
Article; Bai, Renren; Liang, Zhongxing; Yoon, Younghyoun; Salgado, Eric; Feng, Amber; Gurbani, Saumya; Shim, Hyunsuk; European Journal of Medicinal Chemistry; vol. 136; (2017); p. 360 – 371;,
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112101-81-2, name is R-5-(2-Aminopropyl)-2-methoxybenzenesulfonamide, belongs to amides-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. 112101-81-2

EXAMPLE 32 (b) By following the same procedure as in Example 32 (a), (S)(+)-5-[(2-amino-2-methyl)ethyl]-2-methoxybenzenesulfonamide was obtained by using (S)(-)-N-acetyl-5-[(2-amino-2-methyl)ethyl]-2-methoxybenzenesulfonamide as the starting material. Melting point: 273-276 C. (decomposition). Elemental analysis for C10 H17 ClN2 O3 S: [alpha]D24: 6.0 (c=1.01, methanol). cl EXAMPLE 33 (a) In 120 ml of ethanol were dissolved 2.4 g of (R)(-)-5-[(2-amino-2-methyl)ethyl]-2-methoxybenzenesulfonamide and 1.2 g of 2-(o-ethoxyphenoxy)ethyl bromide, and the mixture was refluxed for 16 hours under heating. The solvent was distilled away, and after rendering alkaline the residue by the addition of 10% sodium hydroxide, and the oily material precipitated was extracted with ethyl acetate. The extract solution was washed with a saturated aqueous sodium chloride, and dried over anhydrous magnesium sulfate. The solvent was distilled away, and the residue was subjected to silica-gel column chromatography. The product was eluted with CHCl3 -methanol (9:5) to provide 1.5 g of the crude crystals of (R)(-)-5-[2-[[2-(o-ethoxyphenoxy)ethyl]amino]-2-methylethyl]-2-methoxybenzenesulfonamide, which was treated with HCl-ethanol to give a hydrochloric acid salt of (R)(-)-5-[2-[[2-(o-ethoxyphenoxy)ethyl]amino]-2-methylethyl]-2-methoxybenzenesulfonamide. Melting point: 228-230 C. Elemental analysis for C20 H29 ClN2 O5 S: [alpha]D-24: -4.0 (c=0.35, methanol).

Statistics shows that 112101-81-2 is playing an increasingly important role. we look forward to future research findings about R-5-(2-Aminopropyl)-2-methoxybenzenesulfonamide.

Reference:
Patent; Yamanouchi Pharmaceutical Co., Ltd.; US4731478; (1988); A;,
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6292-59-7, Adding a certain compound to certain chemical reactions, such as: 6292-59-7, name is 4-(tert-Butyl)benzenesulfonamide, belongs to amides-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 6292-59-7.

Example 3: Preparation of propionic acid 2-[6-(4-tert-butyl-benzenesulfonylamino)-5- (2-methoxy-phenoxy)-[2, 2′] bipyrimidinyl-4-yloxy]-ethyl ester compound of formula IV.A mixture of 4-tert butyl benzene sulfonamide (49.5g, 1eq), Potassium phosphate (123.8g, 2.5eq) dimethyl acetamide (500ml, 5vol) was heated to 40¡ãC and maintained for 30-60 minutes. Propionic acid 2-[6-chloro-5-(2-methoxy-phenoxy)-[2,2′] bipyrimidinyl-4-yloxy]-ethyl ester of formula V (100g, 1 eq) was added to the reaction mixture and the reaction mass was heated to 90¡ãC for 24-28 hours. Filtered the inorganic solid and washed the solid with dimethyl acetamide (100ml, 1vol). To the mixture of water (2.5L, 25vol) and concentrated hydrochloric acid (150ml, 1.5Vol) was added the filtrate at 0-5¡ãC. Maintained the stirring for 1-2 hours at 0-5¡ãC .Filtered the solid and washed with water (500ml, 5vol). Dissolved the wet cake in DCM (500ml, 5Vol) and added to a mixture of water (700ml,7vol) and concentrated hydrochloric acid (75ml, 0.75vol) at 10-15¡ãC.Stirred, separated the DCM layer and repeated the washing with mixture of water (700ml, 7vol) and concentrated hydrochloric acid (75ml, 0.75vol) at 10-15¡ãC. Separated the DCM layer and washed with water (500ml, 5vol). Distilled DCM under vacuum at 35-40¡ãC to get title compound (yield 110g, HPLC purity- 85percent).

According to the analysis of related databases, 6292-59-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MATRIX LABORATORIES LTD; GORE, Vinayak; BINDU, Manojkumar; SHINDE, Dattatraya; KOKANE, Dattatrey; GHRAT, Sushant; DANDALA, Ramesh; WO2012/56468; (2012); A1;,
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53297-68-0, 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. 53297-68-0, name is 2-Chloro-4-sulfamoylaniline belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

The title compound was prepared from 2,5-dichlorophenyl isothiocyanate, according to the procedure described in Example 1, Step 1. MS m/z: 247 (M+H)+. Step 2: {[1-(2,5-dichlorophenyl)-1H-tetrazol-5-yl]thio}acetic acid The title compound was prepared from 1-(2,5-dichlorophenyl)-lH-tetrazole-5-thiol according to the procedure described in Example 1, Step 2. ?H NMR (300 MHz, DMSO-d6) 8: 13.16 (bs, 1H), 8.09 (d, J = 2.2 Hz, 1H), 7.94-7.83 (m, 2H), 4.22 (s, 2H). MS m/z: 305 (M+H)+. Step 3: N-[4-(aminosulfonyl)-2-chlorophenyl] -2-( [ 1 -(2,5 -dichlorophenyl)- lH-tetrazol-5- yl]thio } acetamide. The title compound was prepared from ( [ 1 -(2,5-dichlorophenyl)- lH-tetrazol-5- yl] thio}acetic acid and and 4-amino-3-chlorobenzenesulfonamide according to the procedure described in Example 14, Step 2. lH NMR (300 MHz, DMSO-d6) 8: 10.18 bs, (exchangeable proton, <1H), 8.11 (d, J = 2.0 Hz, 1H), 8.00 (d, J = 8.4 Hz, 1H), 7.95-7.84 (m, 3H), 7.76 (dd, J1 = 8.4 Hz, J2 = 2.0 Hz, 1H), 4.50 (s, 2H). MS m/z: 493 (M+H)+. The synthetic route of 53297-68-0 has been constantly updated, and we look forward to future research findings. Reference:
Patent; MERCK & CO., INC.; ISTITUTO DI RICERCHE DI BIOLOGIA MOLECOLARE P. ANGELETTI S.P.A.; WO2005/115147; (2005); A2;,
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