Month: December 2020

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. 156731-40-7, name is 1-(Boc-amino)-3-butene, A new synthetic method of this compound is introduced below., Application In Synthesis of 1-(Boc-amino)-3-butene

Freshly distilled acrolein (2.5ml, 2.1g, 38mmol) and CSA (175mg, 0.752mmol) were added to an ice-cooled solution of N-Boc-butenylamine 25 (644mg, 3.76mmol) in CH2Cl2 (8ml). The resulting solution was stirred at 0C for 15min and at ambient temperature for 45min. The mixture was then washed with satd NaHCO3 solution (10ml) and the organic layer dried (MgSO4). After filtration, the solvent was removed and the residue purified by chromatography on SiO2 (hexane/MTBE 1:1, Rf=0.36) to yield title compound 26 (684mg, 3.01mmol, 80%) as a colorless oil. 1H NMR (500MHz, CDCl3): delta=1.40 (s, 9H), 2.18-2.27 (m, 2H), 2.62-2.70 (m, 2H), 3.17-3.26 (m, 2H), 3.42-3.51 (m, 2H), 4.95-5.06 (m, 2H), 5.66-5.78 (m, 1H), 9.75 (t, J=1.6Hz, 1H)ppm. 13C{1H} NMR (125MHz, CDCl3): delta=28.27 (3CH3), 32.68 (CH2), 33.28 (CH2), 41.24 (CH2), 43.27 (CH2), 43.68 (CH2), 47.02 (CH2), 47.52 (CH2), 79.68 (C), 116.68 (CH2), 135.18 (CH), 154.99 (C), 155.34 (C), 200.72 (CH), 201.03 (CH)ppm. IR (ATR): 3077 (w), 2976 (m), 2930 (w), 1688 (vs), 1478 (m), 1415 (s), 1366 (s), 1249 (m), 1167 (vs), 1064 (m), 913 (m), 773 (m)cm-1. HRMS (CI, isobutane): calcd 228.1600 (for C12H22NO3), found 228.1603 [M+H+]. C12H21NO3 227.30.

The synthetic route of 156731-40-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wuerdemann, Martina; Christoffers, Jens; Tetrahedron; vol. 70; 31; (2014); p. 4640 – 4644;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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. 6873-44-5, name is 4-Chloro-N-methylbenzamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Product Details of 6873-44-5

EXAMPLE IV N-Methyl 4-Chlorobenzimidoyl Chloride N-Methyl 4-chlorobenzamide (42.6 g, 251 mmole) and thionyl chloride (153.3 g, 1.28 mole) were reacted as in Example I to yield 39.3 g (83.4%) of the title compound, b.p. 125 C. (15 mm Hg).

The synthetic route of 6873-44-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; McNeilab, Inc.; US4528382; (1985); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 1314538-55-0, name is Potassium (((tert-butoxycarbonyl)amino)methyl)trifluoroborate, 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 1314538-55-0, Product Details of 1314538-55-0

84- iii (0.27 g, 0.45 mmol, 1 .0 equiv), potassium (((tert-butoxycarbonyl) amino) methyl) trifluoroborate (0.21 g, 0.89 mmol, 2.0 equiv) were added to toluene: water (5: 0.5) and the reaction mixture was degassed for 5 minutes. Pd (ll)OAc (0.005 g, 0.022 mmol, 0.05 equiv), RuPhos (0.02 g, 0.044 mmol, 0.1 equiv), K2CO3 (0.19 g, 1 .34 mmol, 3.0 equiv) were added and the reaction mixture was stirred at 80 C for 24 hours. The reaction mixture was quenched with cold water and extracted with EtOAc. The organic layer was washed with brine, dried over sodium sulfate and concentrated to afford a crude residue. The crude residue was purified by preparative HPLC purification to afford the desired product 85-i (0.038 g, 15 % yield). 1H NMR (400 MHz, MeOD) delta 7.27 (s, 1 H), 7.09 (s, 1 H), 6.43 (s, 1 H), 4.49 (s, 2H), 3.96 – 3.80 (m, 2H), 3.53 (dd, J = 18.0, 5.8 Hz, 5H), 2.47 (s, 3H), 2.23 (d, J = 7.5 Hz, 1 H), 2.18 (d, J = 7.7 Hz, 1 H), 1 .48 (d, J = 10.2 Hz, 18H), 1 .15 (d, J = 5.5 Hz, 1 H), 0.90 (d, J = 7.1 Hz, 1 H), 0.53 – 0.43 (m, 2H) LCMS (m/z): 581 .5 [M+H]

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Potassium (((tert-butoxycarbonyl)amino)methyl)trifluoroborate, and friends who are interested can also refer to it.

Reference:
Patent; NOVARTIS AG; FIDALGO, Javier De Vicente; HE, Haiying; HU, Cheng; JIANG, Zhigan; LI, Xiaolin; LU, Peichao; MERGO, Wosenu; MUTNICK, Daniel; RECK, Folkert; RIVKIN, Alexey; SKEPPER, Colin Kevin; WANG, Xiaojing Michael; XIA, Jianhua; XU, Yongjin; (285 pag.)WO2016/20836; (2016); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 143557-91-9,Some common heterocyclic compound, 143557-91-9, name is tert-Butyl 3-endo-3-hydroxy-8-azabicyclo[3.2.1]octane-8-carboxylate, molecular formula is C12H21NO3, 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.

After dissolving (endo)-3-hydroxy-8-azabicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester (CAS 143557-91-9) (2.00 g) and 1-(3-chloropropyl)-2-fluorobenzene (CAS 110406-96-7) (1.67 g) in N,N-dimethylformamide (10 ml), tetra-n-butylammonium iodide (325 mg) was added to the solution. Sodium hydride (60% in oil) (422 mg) was added and the mixture was stirred at room temperature for 17 hours and 30 minutes. Sodium hydride (60% in oil) (352 mg) was added to the reaction mixture, and stirring was continued for 2 hours at room temperature. Water was added to the reaction mixture, and extraction was performed with ethyl acetate. The organic layer was washed with a saturated aqueous solution of ammonium chloride, water and brine in that order and then dried over anhydrous magnesium sulfate. After filtration, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain the title compound (1.20 g).1H-NMR (400 MHz, CDCl3); delta 1.46 (s, 9H), 1.81-1.95 (m, 8H), 2.06-2.11 (m, 2H), 2.71-2.75 (m, 2H), 3.37-3.38 (m, 2H), 3.54-3.56 (m, 1H), 4.10-4.18 (m, 2H), 6.98-7.07 (m, 2H), 7.14-7.21 (m, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route tert-Butyl 3-endo-3-hydroxy-8-azabicyclo[3.2.1]octane-8-carboxylate, its application will become more common.

Reference:
Patent; Eisai R&D Management Co., Ltd.; US2009/270369; (2009); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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. 70-55-3, name is 4-Methylbenzenesulfonamide, A new synthetic method of this compound is introduced below., Application In Synthesis of 4-Methylbenzenesulfonamide

Example 3 p-Aminosulfonyl-benzoic Acid To the solution of 17.1 g (0.1 mol) of p-toluenesulfonamide prepared in Example 1, 20 g (0.5 mol) of sodium hydroxide in 300 ml of water was added in portions 20 g (0.13 mol) of potassium permanganate. The temperature raised to 70 C. spontaneously, keep the reaction mixture in 90 C. for 2 h. The mixture was then cooled and filtered, and the filtrate was acidified with HCl. The resulting precipitate was filtered, and washed with water, dried in vacuo to give the title compound (18.1 g) as white powder, yield 90%, m.p. 291-292 C.

The synthetic route of 70-55-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Guo, Zongru; Cheng, Guifang; Chu, Fengming; US2004/58977; (2004); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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. 40724-47-8, name is 4-Bromomethylbenzenesulfonamide, A new synthetic method of this compound is introduced below., Recommanded Product: 4-Bromomethylbenzenesulfonamide

Example 7 4-(trityithiomethyi)benzenesulfonamide To a stirred solution of triphenylmethanethiol (0.276g, 2equiv) in N,N- dimethylformamide (3 mL) at 0¡ãC was added sodium hydride (60percent w/w dispersion in mineral oil, 0.04g, 2 equiv). When the effervescence had ceased, 4- (bromomethyi)benzenesuifonamide (0.125g, 1 equiv) was added in a single portion and the reaction was allowed to warm to room temperature. HPLC-MS at 20 minutes indicated that conversion was complete. The reaction was quenched with acetic acid (-0.2 mL), concentrated to dryness in vacuo and the subsequent residue partitioned between ethyl acetate and brine. The organic layer was separated, dried over MgS04, filtered, concentrated and purified by flash chromatography (0-50percent ethyl acetate in hexanes). Fractions containing the desired material were concentrated to dryness to furnish the desired compound as a colourless solid (0.200g). f H NMR (400MHz, DMSO-d6) delta (ppm) H), 7.36-7.44 (m, 12H), 7.67-7.73 (m, 2H)

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; THE CENTRE FOR DRUG RESEARCH AND DEVELOPMENT; WINTERS, Geoffrey C.; MANDEL, Alexander Laurence; RICH, James R.; HEDBERG, Bradley John; HSIEH, Tom Han Hsiao; BOURQUE, Elyse Marie Josee; BABCOOK, John; WO2014/144871; (2014); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Some common heterocyclic compound, 57561-39-4, name is tert-Butyl (2-hydroxyethyl)(methyl)carbamate, molecular formula is C8H17NO3, 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 tert-Butyl (2-hydroxyethyl)(methyl)carbamate

Route ASynthesis of compound 1: 7.5 ml (85 mmol) oxalyl chloride was dissolved in 200 ml DCM and cooled to T < -60 C and 12.1 ml (171 mmol) DMSO in 10 ml DCM was added dropwise (T < -60 C) and stirred an additional 10 min. 10.0 g (57 mmol) N-Boc-N-methylaminoethanol in 40 ml DCM were added dropwise (T < -60 C) and stirred an additional 10 min. 40 ml (285 mmol) Et3N was added dropwise followed by 50 ml DCM (T < -60 C) and stirred for 30 min. The reaction mixture was warmed to 0 C and washed with 3x100 ml water, 100 ml 0.5 M KHS04, 75 ml brine, dried with MgS04 and concentrated in vacuo. The product was purified by column chromatography (Si02, DCM/ethyl acetate, 1 :0 to 9: 1) to give 7.36 g (74%) of compound 1. 1H-NMR (300MHz, CDC13): delta = 1.42/1.46 (s, 9H, Boc), 2.93/2.96 (s, 3H, Me), 3.90/4.01 (s, 2H, CH2), 9.60 (s, 1H, CHO). Z/E isomers. These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 57561-39-4, its application will become more common. Reference:
Patent; SYNTARGA B.V.; BEUSKER, Patrick, Henry; COUMANS, Rudy, Gerardus, Elisabeth; ELGERSMA, Ronald, Christiaan; MENGE, Wiro, Michael, Petrus, Bernardus; JOOSTEN, Johannes, Albertus, Frederikus; SPIJKER, Henri, Johannes; DE GROOT, Franciscus, Marinus, Hendrikus; WO2011/133039; (2011); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 402-46-0, A common heterocyclic compound, 402-46-0, name is 4-Fluorobenzenesulfonamide, molecular formula is C6H6FNO2S, 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.

Example 13; 4-Fluoro-{N-4-[N-(3-fluoro-4-methoxyphenyl)-pyridin-3-ylmethylamino]- benzoyl} benzenesulfonamide; A mixture of 4- [N-(3-fluoro-4-methoxyphenyl)-pyridin-3-ylmethylamino] benzoic acid (50 mg, 0.14 mmol), 4-fluorobenzenesulfonamide (49 mg, 0. 28 mmol), 1- (3-dimethylaminopropyl)-3- ethylcarbodiimide hydrochloride (54 mg, 0.28 mmol), and dimethylaminopyridine (35 mg, 0.28 mmol) was taken up in dichloromethane (1 mL) and stirred for 18h. The mixture was partitioned between EtOAc (50 mL) and 20% aqueous NH40Ac. The EtOAc was separated, washed with brine, dried (MgS04) and concentrated. The residue was purified by column chromatography (silica gel) eluting with 100% EtOAc to give 38 mg of 4-fluoro-f N 4- [N (3-fluoro-4- methoxyphenyl)-pyridin-3-ylmethylamino]-benzoyl} benzenesulfonamide as a white solid. IH NMR (300 MHz, CDC13) 6 8.5-8. 4 (m, 2H), 8. 11 (m, 2H), 7.7-7. 5 (m, 3H), 7.25 (m, 1H), 7.16 (m, 2H), 7.0-6. 8 (m, 3H), 6.63 (d, J=9.0, 2H), 4.92 (s, 2H), 3.89 (s, 3H).

The synthetic route of 402-46-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MEMORY PHARMACEUTICALS CORPORATION; WO2005/61458; (2005); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Some common heterocyclic compound, 3984-14-3, name is N,N-Dimethylsulfamide, molecular formula is C2H8N2O2S, 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: 3984-14-3

A mixture of compound 24-3 (0.465 g, 0.98 mmol) and CDI (0.245 g, 1.57 mmol) in THF (2 mL) was heated at 50 C. for 0.5 h, cooled down and added N,N dimethylsulfamide (0.194 g, 157 mmol) and DBU (0.264 mL, 1.77 mmol). The mixture was stirred for over night. Another portion of DBU (0.13 mL, 0.9 mmol) and the mixture was stirred for another 3 days. The mixture was diluted with EtOAc, washed with cold 1N HCl, brine, dried removed the solvent and purified by flash to afford the Compound 24-4 (0.52 g, 91%). LC-MS retention time: 3.470; MS m/z 579 (M+H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3984-14-3, its application will become more common.

Reference:
Patent; Bristol-Myers Squibb Company; US2008/226593; (2008); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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. 1943-79-9, name is Phenyl methylcarbamate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Safety of Phenyl methylcarbamate

Methane sulfonic acid (1.4 g) was added to a mixture of S-{(3R)-5-oxo-1-[(6-phenoxypyridin-3-yl)methyl]pyrrolidin-3-yl)ethanethioate (1.0 g) obtained in Example 38 and isopropyl alcohol (5 mL), and the mixture was stirred at 90C for 5 hours. The reaction mixture was cooled to 60C, potassium carbonate (2.0 g) and isopropyl alcohol (5 mL) were added thereto, and the mixture was stirred at the same temperature for 1 hour. Tri-n-butylphosphine (59 mg) and phenyl methylcarbamate (0.7 g) were added to the mixture, and stirring was continued at the same temperature for another 1 hour. The mixture was cooled to 0 to 10C, citric acid mono hydrate (1.5 g) was added thereto, and then water was added to the mixture while maintaining the same temperature. The mixture was extracted with ethyl acetate and washed with saturated brine. The organic layer was dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and thus obtained residue was purified by silica gel chromatography (ethyl acetate) to yield 0.7 g (69%) of the title compound. 1H-NMR (CDCl3) delta: 2.40-2.48(1 H, m), 2.82-2.94(3 H, m), 3.23-3.29 (1 H, m), 3.75-3.81(1 H, m), 4.04-4.08(1 H, m), 4.40-4.49(2 H, m), 5.60 (1 H, brs), 6.87 (1 H, d, J=8.4 Hz), 7, 11-7.22(3 H, m), 7.37-7.42(2 H, m), 7.58-7.62(1 H, m), 8.05(1 H, d, J=2.2 Hz).

The synthetic route of 1943-79-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP1500658; (2005); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics