Tag: M.W=100-200

These common heterocyclic compound, 518057-72-2, name is 5-Amino-2-fluorobenzamide, 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. Safety of 5-Amino-2-fluorobenzamide

A mixture of 5-benzyloxy-2-fluoro-6-[4-(trifluoromethoxy)phenoxy]-3- (trifluoromethyl)benzoic acid (40 mg, 0.082 mmol), 5-amino-2-fluoro-benzamide (14 mg, 0.09 mmol), HATU (38 mg, 0.10 mmol) and DIPEA (50 mu, 0.2871 mmol) in DMF (700 mu was stirred at room temperature for 3 hours. The reaction mixture was quenched with water and the precipitated solid was filtered and washed with water. The solid was taken up in DCM, dried over MgSO/i, filtered and concentrated in vacuo. Product was purified by silica gel chromatography (0-50% ethyl acetate/hexanes) to afford 5-benzyloxy-N-(3-carbamoyl-4-fluoro-phenyl)-2-fluoro-6-[4-(trifluoromethoxy)phenoxy]-3- (trifluoromethyl)benzamide (28 mg, 52%). ESI-MS m/z calc. 626.11, found 627.2 (M+l)+; retention time (Method B): 2.09 minutes (3 minutes run). NMR (400 MHz, DMSO-d6) delta 11.01 (s, 1H), 7.89 (dd, J = 6.4, 2.8 Hz, 1H), 7.74 (d, J = 6.7 Hz, 1H), 7.71 – 7.63 (m, 3H), 7.36 – 7.18 (m, 6H), 7.09 – 7.04 (m, 2H), 6.97 – 6.92 (m, 2H), 5.17 (s, 2H) ppm.

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

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; AHMAD, Nadia; ANDERSON, Corey; ARUMUGAM, Vijayalaksmi; ASGIAN, Iuliana, Luci; CAMP, Joanne, Louise; FANNING, Lev Tyler, Dewey; HADIDA RUAH, Sara, Sabina; HURLEY, Dennis; SCHMIDT, Yvonne; SHAW, David; SHETH, Urvi, Jagdishbhai; THOMSON, Stephen, Andrew; (691 pag.)WO2019/14352; (2019); A1;,
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Reference of 480452-05-9,Some common heterocyclic compound, 480452-05-9, name is N-Boc-2-methyl-1,3-propanediamine, molecular formula is C9H20N2O2, 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.

(Step 1) A solution of tert-butyl (3-amino-2-methylpropyl)carbamate (200 mg, 1.06 mmol), 4-cyanobenzoic acid (156 mg, 1.06 mmol), HATU (525 mg,1.38 mmol) and TEA (0.444 mL, 3.19 mmol) in DMF (5 mL) was stirred at room temperature for 16 hr. Water was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was dried, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (solvent gradient; 10 to 50% ethyl acetate/hexane) to give tert-butyl (3-(4-cyanobenzamido)-2-methylpropyl)carbamate (311 mg, 0.980 mmol, 92%) as a white powder. 1H-NMR(300MHz,CDCl3) :delta0.83(3H,d,J=6.8Hz), 1.37(9H,s), 1.74-1.93(1H,m), 2.76-3.00(2H,m), 3.05-3.25(2H,m), 6.82(1H,t,J=5.7Hz), 7.93-8.02(4H,m), 8.65(1H,t,J=5.5Hz)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route N-Boc-2-methyl-1,3-propanediamine, its application will become more common.

Reference:
Patent; Takeda Pharmaceutical Company Limited; YAMAMOTO, Satoshi; SHIRAI, Junya; FUKASE, Yoshiyuki; TOMATA, Yoshihide; SATO, Ayumu; OCHIDA, Atsuko; YONEMORI, Kazuko; NAKAGAWA, Hideyuki; EP2759533; (2014); A1;,
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Synthetic Route of 1122-56-1, 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. 1122-56-1, name is Cyclohexanecarboxamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A mixture of cyclohexane carboxamide (1.1 g, 8.56 mmol) and Lawesson’s reagent (2.08 g, 5.14 mmol) in THF (35 mL) was stirred at 50 C. for 5 h. The reaction mixture was cooled, concentrated in vacuo, and purified by silica gel column chromatography (0-50% EtOAc in hexanes) to yield cyclohexane thioamide (938 mg, 77%).

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

Reference:
Patent; VICURON PHARMACEUTICALS INC.; US2006/211603; (2006); A1;,
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Reference of 627-12-3, 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. 627-12-3, name is Propyl carbamate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: CuI (10mol%) and EDA (10mol%) were added to a mixtureof O-alkyl carbamate (1mmol), NaOtBu (1.5mmol) and aryl halide (1mmol) in 2mL toluene and the mixture wasstirred for the appropriate time, which was determined byTLC monitoring, at 100C. After completion of the reaction,the catalyst was removed by filtration and 20mL H2Owas added to the filtrate. The resultant mixture was extractedwith CHCl3.Then the organic phase was washed with water(2 ¡Á 10mL) and dried over anhydrous Na2SO4.After evaporationof CHCl3under reduced pressure, the correspondingcrude product was purified by flash chromatography to givethe desired pure cross-coupling product in good to excellentyield. In the case of using arylboronic acids as couplingpartners, Cu(OAc)2 was employed instead of CuI.

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

Reference:
Article; Sardarian, Ali Reza; DindarlooInaloo, Iman; Zangiabadi, Milad; Catalysis Letters; vol. 148; 2; (2018); p. 642 – 652;,
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Adding a certain compound to certain chemical reactions, such as: 119023-25-5, name is 2-Amino-4-fluorobenzamide, 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 119023-25-5, Product Details of 119023-25-5

[00304] Step A: To a solution of 2-bromo-2-(4-fluorophenyl)acetic acid (425 mg, 1.82 mmol) in DCM (5 mL) and DMF (0.05 mL) was added oxalyl chloride (0.17 mL, 1.91 mmol) and the solution was stirred for 0.75 h. The solution was then cooled to 0 oC and a solution of 2-amino-4-fluorobenzamide (267 mg, 1.73 mmol) in pyridine (1 mL) was added. The solution was stirred at rt for 1 h and then evaporated. The crude residue was partitioned between EtOAc and 2 N HCl. The EtOAc layer was evaporated to give 2-(2-bromo-2-(4-fluorophenyl)acetamido)-4-fluorobenzamide as a crude oil which was used without further purification. (420 mg, 62%). LC-MS (ESI) m/z 369 (M – H)-.

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; AMBIT BIOSCIENCES CORPORATION; LIU, Gang; CHAO, Qi; HADD, Michael, J.; HOLLADAY, Mark, W.; ABRAHAM, Sunny; SETTI, Eduardo; WO2010/99379; (2010); A1;,
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Adding a certain compound to certain chemical reactions, such as: 38267-76-4, name is tert-Butyl ethylcarbamate, 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 38267-76-4, HPLC of Formula: C7H15NO2

[00753] Step F: 5-chloro-3-(4-(2-fluorophenoxy)cyclohex-1-en-1-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazolo[3,4-c]pyridine (0.75 g, 1.58 mmol) and tert-butyl ethylcarbamate (0.92 g, 6.33 mmol) were dissolved in dioxane (16 mL) and dicyclohexyl(2′,6′-diisopropoxy-[1,1′-biphenyl]-2-yl)phosphane (0.29 g, 0.63 mmol), sodium t-butoxide (0.30 g, 3.2 mmol) and Pd2dba3 (0.29 g, 0.32 mmol) were added and purged with nitrogen. The tube was sealed and heated to 100 C overnight, partitioned between EtOAc and water, extracted with EtOAc, dried over sodium sulfate, filtered and concentrated. The residue was purified over silica gel (10-30% EtOAc in hexanes) to afford tert-butyl ethyl(3-(4-(2-fluorophenoxy)cyclohex-1-en-1-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazolo[3,4-c]pyridin-5-yl)carbamate (615 mg, 66.7% yield).

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, tert-Butyl ethylcarbamate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ARRAY BIOPHARMA INC.; ALLEN, Shelley; BOYS, Mark Laurence; COOK, Adam; GAUDINO, John; HINKLIN, Ronald Jay; LAIRD, Ellen; MCNULTY, Oren T.; METCALF, Andrew T.; NEWHOUSE, Brad; ROBINSON, John E.; (545 pag.)WO2019/113190; (2019); A1;,
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98-64-6, name is 4-Chlorobenzenesulfonamide, 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. category: amides-buliding-blocks

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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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. 5202-85-7, name is 2-Amino-5-chlorobenzamide, A new synthetic method of this compound is introduced below., Formula: C7H7ClN2O

General procedure: 2-aminobenzamide 2 (1.0 mmol) was added to a suspensionof the catalyst 5 (2.1 mmol/g, 0.05 g, 0.1 mmol) inCHCl3 (10 mL) and stirred for 10 min, followed by N-Bocimines 1 (1.1 mmol) and stirred at -15 C for 24-36 h, thereaction was ascertained by TLC. When the reaction wascompleted, the mixture was filtered and washed severaltimes with CHCl3. The filtrate was concentrated and purifiedby silica gel chromatography to obtain pure product.

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; Zhang, Baohua; Shi, Lanxiang; Guo, Ruixia; Catalysis Letters; vol. 145; 9; (2015); p. 1718 – 1723;,
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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. 121492-06-6, name is N-Boc-(2-Aminoethyl)-N-methylamine, A new synthetic method of this compound is introduced below., COA of Formula: C8H18N2O2

tert-Butyl methyl(2-(3-(5-(trifluoromethyl)-1 ,2,4-oxadiazol -3- yI)benzamido)ethyl)carbamate 3-(5-(Trifluoromethyl)-1 ,2,4-oxadiazol-3-yl)benzoic acid (1 .24 g, 4.8 mmol), EDCI(922 mg, 4.8 mmol), HOBt (648 mg, 4.8 mmol), and DIPEA (774 mg, 6mmol) were added to a solution of crude tert-butyl (2-aminoethyl)(methyl)carbamate in DCM (5OmL). The reaction mixture was stirred at room temperature overnight. Water (20 mL) was added to the mixture and the organic phase was separated. The aqueous phase was extracted with CH2CI2 (40 mL x3). The combined organic solvents was washed with brine (30 mL), driedover Na2SO4. After removal of solvents, the crude compound was purified by flash column (EtOAc: PE = 2:1) to provide tert-butyl methyl(2-(3-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)benzamido)ethyl)carbamate as a white solid (1.1 g, yield 66%). MS (ESI) m/z: Calculated for C18H21F3N404: 414.15; found: 437 (M-f-Na).

The synthetic route of 121492-06-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TEMPERO PHARMACEUTICALS, INC.; GHOSH, Shomir; LOBERA, Mercedes; SCHMIDT, Darby, R.; BALOGLU, Erkan; WO2013/6408; (2013); A1;,
Amide – Wikipedia,
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These common heterocyclic compound, 96-30-0, name is 2-Chloro-N-methylacetamide, 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. Recommanded Product: 2-Chloro-N-methylacetamide

Step 3. Preparation of 2-[4-(5-cyano-2-methoxyphenoxy)piperidin-1-yl]-N-methylacetamide (4)4-Methoxy-3-(piperidin-4-yloxy)benzonitrile hydrochloride salt (3, 28.36 g, 95.82 mmoles), 2-chloro-N-methylacetamide (12.37 g, 114.98 mmoles) and potassium carbonate (33.11 g, 239.55 mmoles) were suspended in acetonitrile (161.36 g). The reaction mixture was heated at reflux for 3 hours. The reaction mixture was cooled to 20 C. and water (386.26 g) was charged. The reaction was heated to 75 C. and the volume reduced by distillation. Upon cooling crystallisation occurred. The resulting solid was isolated by filtration, washed twice with water (77.25 g and 128.75 g) and then dried to give the title compound (27.95 g, 94% yield); 1H NMR (400 MHz, DMSO-d6) delta ppm 1.68 (m, 2H) 1.91 (m, 2H) 2.29 (m, 2H) 2.61 (d, J=4.7 Hz, 3H) 2.67 (m, 2H) 2.88 (s, 2H) 3.83 (s, 3H) 4.41 (tt, J=8.3, 4.0 Hz, 1H) 7.11 (d, J=8.4 Hz, 1H) 7.40 (dd, J=8.4, 1.9 Hz, 1H) 7.47 (d, J=1.9 Hz, 1H) 7.68 (q, J=4.7 Hz, 1H); Mass Spectrum: m/z (M+H)+ 304.2.

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

Reference:
Patent; ASTRAZENECA AB; US2009/286982; (2009); A1;,
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