Category: amides-buliding-blocks

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. 164332-88-1, name is tert-Butyl (2-(2-bromoethoxy)ethyl)carbamate, A new synthetic method of this compound is introduced below., Quality Control of tert-Butyl (2-(2-bromoethoxy)ethyl)carbamate

General procedure: A mixture of the alkyl halide, nitrogen-containing compound and excess base (NaH for compounds 80 and 81, Cs2CO3 for other compounds) in DMF was stirredat 60 C for 30 min. The reaction was quenched with water and extracted with EA. The organic layer was washed with water and brine, concentrated and purified by column chromatography.

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; Ngo, Van T.H.; Hoang, Van-Hai; Tran, Phuong-Thao; Ann, Jihyae; Cui, Minghua; Park, Gyungseo; Choi, Sun; Lee, Jiyoun; Kim, Hee; Ha, Hee-Jin; Choi, Kwanghyun; Kim, Young-Ho; Lee, Jeewoo; Bioorganic and Medicinal Chemistry; vol. 26; 5; (2018); p. 1035 – 1049;,
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Adding a certain compound to certain chemical reactions, such as: 239074-29-4, name is tert-Butyl (trans-4-(hydroxymethyl)cyclohexyl)carbamate, 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 239074-29-4, SDS of cas: 239074-29-4

To a stirred solution of tert-butyl ((1R,4R)-4-(hydroxymethyl)cyclohexyl)carbamate (1.5 g, 0.7 mmol, synthesized via Steps 1-2 of Intermediate K) and 1-phenyl-2,5,8,11,14-pentaoxahexadecan-16-yl 4-methylbenzenesulfonate (4.74 g, 0.98 mmol, Intermediate X) in THF (30 mL) was added KOH (3.67 g, 65.4 mmol) at rt. The resulting reaction mixture then heated to 60 C. and stirred for 16 h. The reaction mixture was then transferred into ice water and the resulting mixture was extracted using ethyl acetate (3¡Á100 mL). The combined organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was evaporated under reduced pressure and the crude product was purified using silica gel column chromatography (2% MeOH-DCM) to give tert-butyl ((1R,4R)-4-(18-phenyl-2,5,8,11,14,17-hexaoxaoctadecyl)cyclohexyl)carbamate as a yellow oil (0.92 g, 26%). LC-MS (ESI+) m/z 557.4 (M+18)+.

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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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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. 53250-82-1, name is 4-(Methylsulfonamido)aniline, A new synthetic method of this compound is introduced below., SDS of cas: 53250-82-1

Example 46 (2464) N-(4-((7-Chloro-5-hydroxy-1 ,1 -dioxido-2H-benzore1H ,2,41thiadiazin-3- yl)amino)phenyl)methanesulfonamide (2465) (2466) To a stirred solution of N-(4-aminophenyl)methanesulfonamide (143 mg), KH2P04 (105 mg) in t-BuOH (10 mL) at 0 C was added 3-bromo-7-chloro-5-hydroxy-4H- benzo[e][1 ,2,4]thiadiazine 1 ,1 -dioxide (lnt-3, 200 mg) in portions. The reaction mixture was then stirred at 80 C for 16 hr, cooled to RT, and diluted with cold water. The resulting solid was collected by filtration, washed with diethyl ether and dried under vacuum to afford the titled compound (177.7 mg). LCMS m/z 416.92 (M+H). NMR after D20 exchange (400 MHz, DMSO-c/e) delta ppm 2.97 (s, 3 H) 7.09 (d, J=1 .97 Hz, 1 H) 7.18 (d, J=2.19 Hz, 1 H) 7.25 (d, J=8.77 Hz, 2 H) 7.48 (d, J=8.77 Hz, 2 H).

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; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; ADAMS, Jerry Leroy; ATOR, Laura E.; DUFFY, Kevin J.; GRAYBILL, Todd L.; KIESOW, Terence John; LIAN, Yiqian; MOORE, Michael Lee; RALPH, Jeffrey M.; RIDGERS, Lance Howard; (370 pag.)WO2017/98421; (2017); 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. 154748-63-7, name is tert-Butyl (3-hydroxycyclobutyl)carbamate, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C9H17NO3

To a solution of (3-hydroxy-cyclobutyl)-carbamic acid tert-butyl ester (2.5 g, 13.3 mmol) in THF (40 mL) were added CS2CO3 (8.6 g, 26.6 mmol) and 5-bromo-2,4- dichloro- pyrimidine (3 g, 13.3 mmol). The reaction mixture was heated at reflux overnight. The reaction mixture was filtered and concentrated, diluted with EtOAc and water. The aqueous phase was extracted with EtOAc (3 x 100 mL) and the combined organic extracts were washed with brine (60 mL), dried over MgSO*}, filtered, and concentrated. Purification by flash column chromatography on silica gel to give the product (4.75 g, 12.6 mmol, yield: 95%). ESI-MS (M+l): 378 calc. for CisHnBrClNsOs 377.

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 154748-63-7.

Reference:
Patent; AMGEN INC.; ALLEN, Jennifer; FROHN, Michael; HARRINGTON, Paul; PICKRELL, Alexander; RZASA, Robert; SHAM, Kelvin; HU, Essa; WO2011/143366; (2011); A1;,
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Synthetic Route of 117009-97-9, These common heterocyclic compound, 117009-97-9, name is Benzyl 1,4-diazepane-1-carboxylate, 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.

Synthesis of 4-(1-chloro-8-propoxy-isoquinoline-5-sulfonyl)-[1,4]diazepane-1-carboxylic acid benzyl ester (7) A solution of 1-chloro-8-propoxy-isoquinoline-5-sulfonic acid (5) and 1-chloro-8-propoxy-isoquinoline-7-sulfonic acid (6) (476 mg, 1.58 mmol) in SOCl2 (5 ml) and DMF (0.5 ml) was heated at 80 C for 2 h. The solvent was evaporated. The residue was quenched with H2O and the solution was neutralized (pH = 8) by addition of a saturated NaHCO3 solution. The mixture was extracted with CH2Cl2. The combined organic layers were poured drop wise to a solution of Cbz-homopiperazine (490 mg, 2.09 mmol) in CH2Cl2 (5 ml) at 0 C. The reaction was stirred at 0 C for 2 h. The reaction was washed with water. The organic layers were dried over MgSO4, concentrated and purified by flash chromatography (cyclohexane/EtOAc 10/0 to 8/2) to afford 360 mg (44%) of 4-(1-chloro-8-propoxy-isoquinoline-5-sulfonyl)-[1,4]diazepane-1-carboxylic acid benzyl ester (7) as a yellow oil. 1H NMR (300 MHz,DMSO-d6) delta : 8.37-8.18 (m, 3H), 7.25 (m, 5H), 6.91 (d, J = 8.6 Hz, 1H), 5.02 (s, 2H), 4.13 (t, J = 6.1 Hz, 2H), 3.54-3.46 (m, 4H), 3.36-3.27 (m, 4H), 1.97-1.80 (m, 4H), 1.19 (t, J = 7.1 Hz, 3H).

Statistics shows that Benzyl 1,4-diazepane-1-carboxylate is playing an increasingly important role. we look forward to future research findings about 117009-97-9.

Reference:
Patent; Sygnis Bioscience GmbH & Co. KG; EP2332917; (2011); A1;,
Amide – Wikipedia,
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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. 459817-82-4, name is tert-Butyl 1,2,3-oxathiazolidine-3-carboxylate 2,2-dioxide, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 459817-82-4

Step 1: tert-butyl (2-(2-bromo-4-chloropyridin-3-yl)ethyl)carbamate. 94-1 To a stirred solution of LDA (5.98 mmol) in THF (50 mL) 2-bromo-4-chloropyridine (1.0 g, 5.20 mmol) was added at -70 C. and the resulting solution was stirred at -70 C. for 1 h. Then a solution of tert-butyl 1,2,3-oxathiazolidine-3-carboxylate 2,2-dioxide (1.39 g, 6.24 mmol) in THF (20 mL) was added at -70 C. and the reaction mixture was stirred for 3 h. Saturated aqueous NH4Cl solution was added at -70 C. and the mixture was allowed to warm to RT. The mixture was extracted with AcOEt (2*). The combined organic layers were washed with brine, dried with sodium sulfate, filtered and the solvent was removed under reduced pressure. The crude product was purified by flash-column chromatography over silicagel (Biotage Isolera One, eluent: gradient from 2% MeOH in DCM to 13% MeOH in DCM in 12 min) to yield the title compound as a white solid (1.36 g). UPLC-MS: MS 335.1 (M+H+); UPLC rt 1.06 min.

According to the analysis of related databases, 459817-82-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NOVARTIS AG; BEHNKE, Dirk; CARCACHE, David; ERTL, Peter; KOLLER, Manuel; ORAIN, David; US2014/57902; (2014); A1;,
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Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 33045-52-2, name is Methyl 2-methoxy-5-sulfamoylbenzoate, 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 33045-52-2, HPLC of Formula: C9H11NO5S

Methyl 2-methoxy-5-sulfamoylbenzoate(4.91g, 20mmol) was dissolved in methanol(30mL). 2N Aqueous sodium hydroxide(30mL, 60mmol) was added, and the mixture was stirred at room temperature for 1 hour. The reaction mixture was poured into 2N hydrochloric acid, and the separated solid was filtered to give the title compound(4.55g, 98.3%) as a white solid.1H-NMR(DMSO-d6): delta 3.89(3H, s), 7.30(1H, d, J=8.7Hz), 7.32(2H, s), 7.92(1H, dd, J=8.7, 2.7Hz), 8.09(1H, d, J=2.7Hz), 13.03(1H, br).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Institute of Medicinal Molecular Design, Inc.; EP1514544; (2005); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 25823-52-3, These common heterocyclic compound, 25823-52-3, name is 6,7-Dihydro-2H-benzo[6,7]cyclohepta[1,2-c]pyridazin-3(5H)-one, 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.

Synthetic Preparation 8 Compound of Formula (Df) A mixture of the compound of formula (De), 8,9-benzo-6,7-dihydro-2H-cyclohepta[c]pyridazin-3(5H)-one, (4.0 g, 19.3 mmol) and POCl3 (20 mL) was refluxed for 2 h. After cooling to ambient temperature, the volatiles were evaporated. The residue was poured into a mixture of ice water and sodium bicarbonate, CH2Cl2 (200 mL) was added to dissolve the solid. The layers were separated, and the aqueous layer was extracted with CH2Cl2 one more time. The combined organic layers were washed with brine. After being dried (MgSO4), filtered, and concentrated, the compound of formula (Df), 8,9-benzo-3-chloro-6,7-dihydro-5H-cyclohepta[c]pyridazine, was obtained as a yellow solid (4.3 g, 99%), 1H NMR (300 MHz, CDCl3) delta: 7.82 (m, 1H), 7.45-7.24 (m, 4H), 2.59-2.51 (m, 4H), 2.27 (quant, J=6.9 Hz, 2H); LC-MS: purity: 100%; MS (m/e): 231 (MH+).

The synthetic route of 25823-52-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Rigel Pharmaceuticals, Inc.; US2009/111816; (2009); A1;,
Amide – Wikipedia,
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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. 98-64-6, name is 4-Chlorobenzenesulfonamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. HPLC of Formula: C6H6ClNO2S

General procedure: To a mixture of PS-tet-Cu(II) 2 (0.05 g) and arylboronicacid (0.7 mmol) in water (5 mL), K2CO3(1 mmol), sulfonamide(0.7 mmol) and water (5 mL) was added and the mixture was vig-orously stirred for the appropriate times under reflux conditions.After completion (as monitored by TLC), the catalyst was filteredand the reaction mixture was cooled to room temperature. Theresulting product was filtered and purified by recrystallizationusing ethyl acetate and n-hexane to afford N-arylated product. Allcompounds were compared with the corresponding compoundsprepared by the reported procedure [4,23?40]. All compounds wereknown and were characterized by spectral analysis or meltingpoints.1H NMR data of some compounds are given below.

The synthetic route of 98-64-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Nasrollahzadeh, Mahmoud; Rostami-Vartooni, Akbar; Ehsani, Ali; Moghadam, Majid; Journal of Molecular Catalysis A: Chemical; vol. 387; (2014); p. 123 – 129;,
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These common heterocyclic compound, 2675-89-0, name is 2-Chloro-N,N-dimethylacetamide, 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. Application In Synthesis of 2-Chloro-N,N-dimethylacetamide

Example 5.3Preparation of nC10H21-O-CH2-CONMe2 (Product 3-R1=nC10H21)In a 250 mL reactor, under a nitrogen atmosphere, is introduced sodium hydride, (60% suspended in mineral oil) (5 g, 125 mmol). This product is washed with pentane (3¡Á15 mL) and is then suspended in THF (100 g). The suspension is cooled to 0 C., n-decanol (17.4 g, 110 mmol) is introduced with a syringe. The chlorodimethylacetamide (12.1 g, 100 mmol) is then slowly added onto the mixture. The temperature of the reaction mixture is brought back to room temperature and the reaction mixture is maintained with stirring for 20 hours. The reaction mixture is neutralized with cold water (20 mL) and then this aqueous phase is extracted with dichloromethane (200 mL), the organic phase is washed with a saturated solution of NH4Cl (50 mL), a saturated solution of NaHCO3 (50 mL) and then with water (50 mL). The organic phase is dried on sodium sulfate and concentrated under reduced pressure in order to obtain 20.6 g of the expected product with a purity>98% i.e. a yield of 82%.

The synthetic route of 2-Chloro-N,N-dimethylacetamide has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Vidal, Thierry; Guglieri, Massimo; Jentzer, Olivier; US2012/302791; (2012); A1;,
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