Tag: M.W=100-200

Adding a certain compound to certain chemical reactions, such as: 37045-73-1, name is 3-(Methylsulfonamido)aniline, 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 37045-73-1, Computed Properties of C7H10N2O2S

General procedure: To a solution of N-[4-[5-(3-aminophenyl)-1,2,4-oxadiazol-3-yl]-3-chlorophenyl]-3-pyridinecarboxamide (VIc)(0.2 g, 0.51 mmol, 1 equiv) in THF (20 ml) was added phosgene(15wt % in toluene, 1.7 ml, 2.55 mmol, 5.0 equiv) and the reactionmixture was refluxed under N2 for 4 h. Upon the reactioncompletion as indicated by TLC the solution was concentratedunder reduced pressure, flushed with dry toluene. To theresulting residuewas added THF (20 ml), the appropriate aniline(0.77 mmol, 1.5 equiv) and DIPEA (0.132 g, 178 ml, 1.02 mmol, 2equiv) and the reaction mixture was refluxed under N2 overnight.Upon completion of the reaction as indicated by TLC, thesolution was concentrated, and the residue was purified bychromatography to give the desired final products (25-50).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-(Methylsulfonamido)aniline, and friends who are interested can also refer to it.

Reference:
Article; Dokla, Eman M.E.; Fang, Chun-Sheng; Abouzid, Khaled A.M.; Chen, Ching S.; European Journal of Medicinal Chemistry; vol. 182; (2019);,
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These common heterocyclic compound, 193751-54-1, name is tert-Butyl cyclopent-3-en-1-ylcarbamate, 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. Formula: C10H17NO2

Solid NAHCO3 (0.0167 mol) and M-CPBA (0. 0128 mol) were added in portions to a stirred solution of cyclopent-3-enyl-carbamic acid tert-butyl ester IV-1 (0.0093 mol) in CH2C12 (60 mL). The mixture was stirred at 0 C for the first 2 h of the reaction and then allowed to stir for about 48 h at room temperature. Aqueous 20% NA2S03 (30 mL) was added, and the two layers were separated. The aqueous layer was extracted with CH2C12 (20 mL X 3), and the combined organic layers were washed with 20% NA2SO3 (30 mL X 1), 5 % NAHCO3 (30 mL X 1), and water (30 mL X 1). The combined organic phase was concentrated in vacuo, and the residue was purified by column chromatography (silica gel, 100% dichloromethane) to give pure product as a colorless oil (64%).

The synthetic route of tert-Butyl cyclopent-3-en-1-ylcarbamate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NORTHWESTERN UNIVERSITY; WO2005/26111; (2005); A2;,
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Synthetic Route of 63920-73-0,Some common heterocyclic compound, 63920-73-0, name is 2-Amino-4,6-dimethoxybenzamide, molecular formula is C9H12N2O3, 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 126 Preparation of 5,7-Dimethoxy-2-(3-methoxyphenyl)quinazolin-4(3H)-one A mixture of 2-amino-4,6-dimethoxybenzamide (0.0600 g, 0.306 mmol), 3-methoxybenzaldehyde (0.306 mmol), NaHSO3 (94%, 0.0474 g, 0.428 mmol), and p-TsOH.H2O (0.0175 g, 0.0918 mmol) in DMA (3.06 mL) was heated at 140 C. for 20 hours. The mixture was diluted with EtOAc (300 mL), washed with water (3*75 mL), then brine (75 mL), dried over sodium sulfate, filtered, and concentrated under vacuum. The residue was purified on silica gel (40 g, CH2Cl2/MeOH) and the product was freeze-dried from MeCN/H2O to provide the title compound (69%) as an off-white solid. 1H NMR (300 MHz, DMSO-d6): delta 12.04 (s, 1H), 7.82-7.70 (m, 2H), 7.43 (t, J=7.98 Hz, 1H), 7.13 (dd, J=8.19, 2.46 Hz, 1H), 6.76 (d, J=2.19 Hz, 1H), 6.55 (d, J=2.19 Hz, 1H), 3.92-3.82 (m, 9H); MS (APCI) m/z 313 [C17H16N2O4+H]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Amino-4,6-dimethoxybenzamide, its application will become more common.

Reference:
Patent; Resverlogix Corp.; Hansen, Henrik C.; (96 pag.)US9238640; (2016); B2;,
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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. 683-57-8, name is 2-Bromoacetamide, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 2-Bromoacetamide

Example 304J 2-({3-[1-(cyclobutylamino)-4-hydroxy-2-oxo-1,2-dihydroquinolin-3-yl]-1,1-dioxido-4H-1,2,4-benzothiadiazin-7-yl}oxy)acetamide The product of Example 3041 (0.048 g, 0.11 mmol) in N,N-dimethylformamide (2 ML) was reacted with cesium carbonate (0.15 g, 0.45 mmol), bromoacetamide (0.026 ML, 0.18 mmol), and a catalytic amount of tetrabutylammonium iodide at 25 C. for 3 hours.The reaction was concentrated under a stream of nitrogen stream of nitrogen warmed through a manifold heated to 165 C. and the resulting residue was triturated with water, filtered and dried.The resulting solid was triturated in hot ethyl acetate, filtered, and dried to give the title compound (0.020 g, 37%). MS (ESI-) m/z 482 (M-H)-. 1H NMR (300 MHz, DMSO-d6) delta ppm 1.59 (m, 2H) 1.99 (m, 4H) 3.60 (m, 1H) 4.49 (s, 2H) 6.08 (d, J=6.62 Hz, 1H) 7.05 (t, J=7.17 Hz, 1H) 7.20 (m, 3H) 7.40 (s, 1H) 7.50 (m, 1H) 7.65 (m, 2H) 8.05 (d, J=7.72 Hz, 1H) 16.25 (s, 1H).The sodium salt of the title compound was prepared according to the procedure of Example 1D. 1H NMR (300 MHz, DMSO-d6) delta ppm 1.59 (m, 1H) 1.99 (m, 4H) 3.61 (m, 2H) 4.49 (s, 2H) 6.08 (d, J=6.62 Hz, 1H) 7.05 (m, 1H) 7.21 (m, 2H) 7.40 (s, 2H) 7.50 (m, 1H) 7.64 (m, 2H) 8.06 (dd, J=7.91, 1.29 Hz, 1H) 8.32 (s, 1H).

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 683-57-8.

Reference:
Patent; Pratt, John K.; Betebenner, David A.; Donner, Pamela L.; Green, Brian E.; Kempf, Dale J.; McDaniel, Keith F.; Maring, Clarence J.; Stoll, Vincent S.; Zhang, Rong; US2004/167123; (2004); A1;,
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Adding a certain compound to certain chemical reactions, such as: 6083-47-2, name is 4-(Dimethylamino)benzamide, 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 6083-47-2, 6083-47-2

General procedure: A 12 mL vial was charged with Pd(OAc)2 (2 mol%), BuPAd2 (6 mol%), and a stirring bar. Then, 2 ml dioxane and 1 mmol of bromobenzene were injected by syringe. The vial (or several vials) was placed in an alloy plate, which was transferred into a 300 mL autoclave of the 4560 series from Parr Instruments under argon atmosphere. After flushing the autoclave three times with NH3, a pressure of 2 bar NH3 and 2 bar CO was adjusted at ambient temperature. Then, the reaction was performed for 16 hours at 100 oC. After the reaction is finished, the autoclave was cooled down to room temperature and the pressure was released carefully. Then, CuI (5 mol%), DMEDA (10%), K2CO3 (3 mmol) and 1,2-dibromobenzene were added in under air, the vial was closed and heated to 110oC for 20 hours. The reaction mixture cooled down to room temperature. The solution was extracted 3-5 times with 2-3 ml of ethyl acetate from aqua solution. After evaporation of the organic solvent the residue was adsorbed on silica gel and the crude product was purified by column chromatography using n-heptane/AcOEt (20:1) as eluent.

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-(Dimethylamino)benzamide, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Wu, Xiao-Feng; Neumann, Helfried; Neumann, Stephan; Beller, Matthias; Tetrahedron Letters; vol. 54; 24; (2013); p. 3040 – 3042;,
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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. 121492-06-6, name is N-Boc-(2-Aminoethyl)-N-methylamine, This compound has unique chemical properties. The synthetic route is as follows., 121492-06-6

General procedure: 5-Amino-(30-[N0-methyl-N0-tert-butoxycarbonyl]propyl)-3-(N,N-dimethylcarbox-amide)-6-nitrochromane (9a).[29]A mixture of 5-chloro-3-N,N-dimethyl-carboxamide-6-nitro-chromane (8) (300 mg, 1.10 mmol), primary amine N-Boc-N-methyl-1,3-trimethylenediamine (18) (5.50 mmol),and N-methyl-pyrrolidinone (1.0 mL) was heated in a sealedtube at 758C for 48 h. The reaction mixture was poured into amixture of diethyl ether and water (1 : 1, 80 mL) and the mixturestirred for 30 min. The mixture was transferred to a separationfunnel and the ether layer washed with water (4 25 mL). Theorganic phase was dried over anhydrous sodium sulfate, filtered,and evaporated under reduced pressure. The crude product waspurified by flash chromatography (silica gel, 5 % methanol indichloromethane). The product 9a[29]was isolated as a brightyellow oil (381 mg, 87 %).

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:
Article; Schmit, David; Milewicz, Urszula; Boerneke, Mark A.; Burley, Scott; Walsworth, Kevin; Um, Joann; Hecht, David; Hermann, Thomas; Bergdahl, B. Mikael; Australian Journal of Chemistry; (2020);,
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A common heterocyclic compound, 88-96-0, name is Phthalamide, molecular formula is C8H8N2O2, 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. 88-96-0.

Example 20B (404 mg, 1.13 mmol), triphenylphosphine (455 mg, 1.6 eq.) and phthalamide (222 mg, 1.4 eq.) were mixed in 3.5 mL of toluene. Then, di-tert-butylazodicarboxylate (DBAD, 398 mg, 1.6 eq.) was added. The reaction flask was flushed with argon and then heated to 90 C. After stirring overnight at 90 C., the mixture was cooled to room temperature, concentrated and the resulting oil was purified by column chromatography (eluding with 20% to 40% ethyl acetate in hexane) to give the title compound (684 mg).

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

Reference:
Patent; Pei, Zhonghua; Geldern, Thomas von; Madar, David J.; Li, Xiaofeng; Basha, Fatima; Yong, Hong; Longenecker, Kenton L.; Backes, Bradley J.; Judd, Andrew S.; Mulhern, Matthew M.; Stewart, Kent D.; US2007/49596; (2007); A1;,
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869494-16-6, 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. 869494-16-6, name is tert-Butyl 3,6-diazabicyclo[3.1.1]heptane-6-carboxylate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

(5-Amino-1-[4-(2-fluorophenoxy)-2-methylphenyl]pyrazol-4-yl}-[6-bromo-5-(2-bromoethoxy)-1H-indol-2-yl]methanone (100 mg) was suspended in acetonitrile (1.0 mL), tert-butyl 3,6-diazabicyclo[3.1.1]heptane-6-carboxylate (63 mg) and cesium carbonate (130 mg) were added, and the mixture was stirred at 70¡ãC for three hours. Water was added to the reaction solution, the mixture was extracted with ethyl acetate, and the organic layer was dried over sodium sulfate. After removing the drying agent by filtration, the filtrate was concentrated under reduced pressure, and the resulting residue was purified by column chromatography (hexane/ethyl acetate) to give the target compound (79 mg).

The synthetic route of 869494-16-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chugai Seiyaku Kabushiki Kaisha; F. Hoffmann-La Roche AG; EBIIKE, Hirosato; AOKI, Toshihiro; CHIBA, Takashi; KOCHI, Masami; NAKAMA, Kimitaka; NIIZUMA, Satoshi; NISHII, Hiroki; OHWADA, Jun; SHIMAMURA, Hiroyuki; SUGE, Aiko; NAKANISHI, Yoshito; KOBAYASHI, Natsuki; (594 pag.)EP3312172; (2018); 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. 148017-28-1, name is tert-Butyl sulfamoylcarbamate, A new synthetic method of this compound is introduced below., 148017-28-1

Example 16 N-(4-{4-[3-(2-sulfamoylaminoethoxy)azetidin-1-yl]phenylamino}-6-methoxypyridin-3-yl)acetamide (16a) N-(4-{4-[3-(2-tert-butoxycarbonylsulfamoylaminoethoxy)azetidin-1-yl]phenylamino}-6-methoxypyridin-3-yl)acetamide N-(4-{4-[3-(2-Hydroxyethoxy)azetidin-1-yl]phenylamino}-6-methoxypyridin-3-yl)acetamide (850 mg, 2.28 mmol) produced in Example 1 (1f), N-tert-butoxycarbonylsulfamoyl amine (0.67 g, 3.4 mmol), and triphenylphosphine (0.72 g, 2.7 mmol) were suspended in ethyl acetate:tetrahydrofuran (3:1, 15 mL), diethyl azodicarboxylate (0.74 mL, 3.4 mmol) was added, and the mixture was stirred at room temperature for 20 hr. The solvent of the reaction mixture was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (chloroform:methanol, 100:0?100:4, V/V). The solvent of the object fraction was evaporated under reduced pressure to give the title object compound as a pale-yellow foam-like powder (1.05 g, yield 84%). 1H-NMR (CDCl3, 400 MHz) delta: 1.55 (9H, s), 1.96 (1H, s), 2.24 (2H, s), 3.61 (2H, t, J=5.3 Hz), 3.66-3.74 (2H, m), 3.82 (2H, s), 3.85 (1H, s), 3.98 (2H, t, J=5.3 Hz), 4.00-4.08 (2H, m), 4.38-4.46 (1H, m), 5.44-5.55 (2H, br), 6.10 (0.35H, s), 6.12 (0.35H, s), 6.15 (0.65H, s), 6.34 (0.65H, s), 6.41-6.50 (2H, m), 6.54 (0.65H, s), 6.98-7.07 (2.35H, m), 7.78 (0.65H, s), 7.79 (0.35H, s).

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; Kyoto Pharmaceutical Industries, Ltd.; SHIRAHASE, Hiroaki; TAKAHASHI, Kenji; SHOJI, Yoshimichi; TAKEDA, Shigemitsu; (111 pag.)US2016/207883; (2016); A1;,
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1882-71-9, The chemical industry reduces the impact on the environment during synthesis 1882-71-9, name is 2-Amino-5-methoxybenzamide, I believe this compound will play a more active role in future production and life.

General procedure: A mixture of 2-aminobenzamide (1, 4.0 mmol), carboxamide (2, 6.0 mmol), Yb(OTf)3 (0.20 mmol,5.0 molpercent), and mesitylene (5.0 mL) was placed in a 20-mL Pyrex flask equipped with a magnetic stirring bar and a reflux condenser under a flow of argon. The reaction was carried out at 120-165 oC (bath temp.) for 6 h with stirring. Then, the reaction mixture was cooled to room temperature, and analyzed by GLC, GC-MS (EI), and LC-MS (ESI). After evaporation of mesitylene under vacuum,the products (3) were isolated by recrystallization from MeOH/hexane and/or medium pressure column chromatography on silica gel (eluent: EtOAc/hexane = 50/50 ~ EtOAc 100percent. For 3j, eluent:MeOH/CHCl3 = 50/50). 1H NMR spectra were recorded at 400 MHz, and 13C NMR spectra wererecorded at 100 MHz in DMSO-d6. The analytical and spectral data of 3a-e,38 3f,39 3g,40 3h,41 and3j,42 were consistent with those reported previously. The product, 3i, was characterized below.

The chemical industry reduces the impact on the environment during synthesis 2-Amino-5-methoxybenzamide. I believe this compound will play a more active role in future production and life.

Reference:
Article; Yoshimura, Tsutomu; Yuanjun, Di; Kimura, Yu; Yamada, Hisatsugu; Toshimitsu, Akio; Kondo, Teruyuki; Heterocycles; vol. 90; 2; (2015); p. 857 – 865;,
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