Month: January 2021

Reference of 57957-24-1,Some common heterocyclic compound, 57957-24-1, name is N-(1-Phenylvinyl)acetamide, molecular formula is C10H11NO, 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 12. Asymmetric hydrogenation of different unsaturated hydrocarbon compounds with chiral ligand 6 and [Rh(nbd)2]BF4 at room temperature.The following compounds were hydrogenated in presence of a catalyst of the invention (ligand 6 and [Rh(nbd)2]BF4) at room temperature.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route N-(1-Phenylvinyl)acetamide, its application will become more common.

Reference:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Some common heterocyclic compound, 610302-03-9, name is tert-Butyl (3-hydroxycyclohexyl)carbamate, molecular formula is C11H21NO3, 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: C11H21NO3

XV.2 3-Methylamino-cyclohexanol Prepared analogously to XII.2 from 0.933 g (3-hydroxy-cyclohexyl)-carbamic acid tert-butyl ester. Yield: 0.203 g

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 610302-03-9, its application will become more common.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2011/217311; (2011); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 563-83-7,Some common heterocyclic compound, 563-83-7, name is Isobutyramide, molecular formula is C4H9NO, 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.

A solution of 2-methylpropanamide (6.53 g, 75.0 mmol) and 2,4-bis(4- methoxyphenyl)-1 ,3-dithia-2,4-diphosphetane-2,4-disulfide (15.17 g, 37.51 mmol) in THF (100 ml.) was heated to reflux for 4 h. The reaction mixture was then cooled to rt and poured into saturated aqueous NaHCOs (200 ml_). The mixture was extracted with ether (4 x 100 ml_). The organic fractions were combined, dried over Na2SO4, filtered, and concentrated. Purification by flash column chromatography (20% EtOAc:hexanes) afforded 4.77 g (62%) of the title compound of Step A. 1H NMR (400 MHz, CDCI3) delta 7.63 (br s, 1 H), 6.90 (br s, 1 H), 2.88 (m, 1 H), and 1.27 (d, 6H, J = 6.8 Hz).

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

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2009/32667; (2009); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 53297-70-4, 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 53297-70-4 as follows.

General procedure: The chlorides 9a-j was dissolved in CH2Cl2 (20 mL) andadded dropwise to a stirred solution of 4-anilinesulfonamide(10.0 mmol) and NaHCO3 (1.26 g, 15.0 mmol) in CH3CN(80 mL). The mixture was heated at 70 C for 2h. The solution solutionwas evaporated, and poured to water, filtered to give asolid. This was purified by chromatography on silica gelusing CH2C12-MeOH (30: l) to give the title molecules 10a-t.The typical compound 10c was characterized with NMR andMS techniques. The detailed data is below.

According to the analysis of related databases, 53297-70-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Song, Zhendong; Wang, Ping; Huang, Shanshan; Wang, Changyuan; Wang, Rui-Rui; Yang, Liu-Meng; Zhen, Yuhong; Liu, Kexin; Zheng, Yong-Tang; Ma, Xiaodong; Medicinal Chemistry; vol. 13; 4; (2017); p. 398 – 405;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 6228-73-5, name is Cyclopropanecarboxamide, 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 6228-73-5, Recommanded Product: Cyclopropanecarboxamide

Mix the compound obtained in Step 2 (350 mg, 1.24 mmol), cyclopropanecarboxamide (116 mg, 1.36 mmol), (+-)-2,2′-bis(diphenylphosphino)-1,1′-binaphthalene (BINAP, 77 mg, 0.124 mmol), Cs2CO3 (1.01 g, 3.1 mmol) in 1,4-dioxane (30 mL), then under N2 atmosphere, add tris(dibenzylideneacetone)dipalladium [Pd2(dba)3, 113 mg, 0.124 mmol]. Stir the reaction at 126 C. under N2 for 16 hrs. Cool the reaction mixture, filter, and concentrate the filtrate under reduced pressure to give the crude product. Purification by chromatography (silica gel, EtOAc_PE=1:1) affords the title compound (178 mg, 43.3%). MS: (M+1): 332.2.

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, Cyclopropanecarboxamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Zhang, Deyi; Zhang, Ruihao; Zhong, Boyu; Shih, Chuan; US2015/197511; (2015); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 1015-89-0, 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 1015-89-0 as follows.

Phenanthridin-6(5H)-one (1; 1.017 g, 5.209 mmol) was placed in aSchlenk flask under argon. Freshly distilled CH2Cl2 (30 mL) was added,and the resulting solution was cooled to 0 C. Tf2O (3.00 g, 1.74 mL,10.6 mmol, 2.0 equiv) was added dropwise to the suspension. After40 min, the mixture became almost completely homogeneous. After afurther 20 min of stirring, pyridine (0.414 g, 423 muL, 5.233 mmol, 1.02equiv) was slowly added and a precipitate formed. The resulting mixturewas stirred at 0 C for 40 min. Next, H2O (20 mL) was added andthe mixture was extracted with CH2Cl2 (2 ¡Á 30 mL). The organic layerwas dried (Na2SO4), filtered, and concentrated on a rotary evaporator.The resulting residue was dissolved in Et2O (10 mL) and hexane (60mL) was added. Most of the volatiles were then slowly removed on arotary evaporator. The resulting suspension was filtered to give abeige solid; 1.551 g (91%); mp 82-83 C (Et2O-hexane); Rf = 0.57(hexane-EtOAc, 5:1).IR (CHCl3): 3082, 3047, 1629, 1615, 1467, 1426, 1244, 1216, 1137,1023, 607 cm-1.1H NMR (600 MHz, acetone-d6): delta = 9.00 (ddt, J = 8.3, 1.1, 0.6 Hz, 1 H,H-6), 8.89 (ddt, J = 8.1, 1.4, 0.6 Hz, 1 H, H-11), 8.34 (ddd, J = 8.3, 1.4,0.7 Hz, 1 H, H-3), 8.19 (ddd, J = 8.3, 7.1, 1.4 Hz, 1 H, H-5), 8.11 (ddd,J = 8.0, 1.5, 0.7 Hz, 1 H, H-14), 8.02 (ddd, J = 8.3, 7.1, 1.1 Hz, 1 H, H-4),7.94 (ddd, J = 8.0, 7.1, 1.4 Hz, 1 H, H-13), 7.90 (ddd, J = 8.1, 7.1, 1.5 Hz,1 H, H-12).13C NMR (151 MHz, acetone-d6): delta = 152.50 (C-2), 141.70 (C-8),137.27 (C-10), 134.08 (C-5), 130.96 (C-13), 130.10 (C-4), 129.92 (C-14), 129.35 (C-12), 125.53 (C-7), 124.73 (C-3), 124.02 (C-6), 123.93(C-11), 119.50 (q, JC-F = 320 Hz, CF3), 119.10 (C-9).MS (ESI): m/z (%) = 350.1 [M + Na]+ (100).HRMS (ESI): m/z [M + H]+ calcd for C14H9F3NO3S: 328.0250; found:328.0250.

According to the analysis of related databases, 1015-89-0, the application of this compound in the production field has become more and more popular.

Reference:
Article; Sonawane, Manoj R.; Vavra, Jan; ?aman, David; Cisa?ova, Ivana; Teply, Filip; Synthesis; vol. 47; 22; (2015); p. 3479 – 3488;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 112257-19-9, These common heterocyclic compound, 112257-19-9, name is tert-Butyl methyl(2-(methylamino)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.

Step 6: tent-Butyl (2-(((3-iodo-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-4-yl)methyl)(methyl)amino)ethyl)(methyl)carbamate [0204] 3-iodo-1-(oxan-2-yl)-1H-pyrazole-4-carbaldehyde (21.5 g, 70.24 mmol, 1.00 equiv), tert-butyl N-methyl-N-(2-(methylamino)ethyl)carbamate (20 g, 106.23 mmol, 1.51 equiv) and NaBH(OAc)3 (29.8 g, 137.98 mmol, 1.96 equiv) in dichloroethane (300 mL) was stirred for 1 h at room temperature. The reaction was diluted with 300 mL of dichloromethane and then washed with 3¡Á300 mL of brine. The organic layer was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was purified on a silica gel column eluted with 0-7percent methanol in dichloromethane to give 31 g (92percent) of tert-butyl (2-(((3-iodo-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-4-yl)methyl)(methyl)amino)ethyl)(methyl)carbamate as a yellow oil. 1H NMR (300 MHz, CDCl3): delta 7.62 (s, 1H), 5.34-5.30 (m, 1H), 4.06-4.02 (m, 1H), 3.68-3.62 (m, 1H), 3.42-3.38 (m, 4H), 2.85 (s, 4H), 2.62-2.53 (m, 2H), 2.47-2.46 (m, 2H), 2.13-1.97 (m, 3H), 1.74-1.69 (m, 3H), 1.46 (s, 9H) ppm. LCMS (method A, ESI): RT=1.17 min, m/z=479.0 [M+H]+.

The synthetic route of 112257-19-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Epizyme, Inc.; Mitchell, Lorna Helen; Shapiro, Gideon; Chesworth, Richard; Boriack-Sjodin, Paula Ann; Moradei, Oscar Miguel; US2014/288140; (2014); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 150349-36-3,Some common heterocyclic compound, 150349-36-3, name is 3-(N-Boc-N-methylamino)propylamine, 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.

Ethyl theophylline-7-acetate 2 (266mg, 1 mmol) was suspended in ethanol (1 mL) in a conical vial and N-methyl-N-Bocpropane-1,3-diamine (330 mg, 1.75 mmol) was added. The vial was sealed and heated up to 110OC for 2 h. After purification by column chromatography (DCM/MeOH/Et3N95:5:1 ? 80:20:1), Boc group was removed by stirring intermediate 3b in 4M HCl(5mL). Aliquote of crude reaction mixture (1/3 rd) was neutralized with concentrated NaHCO3 and inorganic salts were precipitated by addition of ethanol (100 mL). After filtration, the solvents were removed in vacuo and the residue was recrystallized from ethyl acetate (hot solution was filtered to eliminate residual traces of inorganic salts). Monomethylated compound 4 was obtained as white solid in 20% unoptimized yield (60mg, 0.2 mmol)

The synthetic route of 150349-36-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Gibon, Julien; Kang, Min Su; Aliaga, Arturo; Sharif, Behrang; Rosa-Neto, Pedro; Seguela, Philippe; Barker, Philip A.; Kostikov, Alexey; Bioorganic and Medicinal Chemistry; vol. 24; 19; (2016); p. 4759 – 4765;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route 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.

To a solution of (trans)-3-hydroxy-8-aza-bicyclo [3.2. 1] [OCTANE-8-CARBOXYLIC] acid tert-butyl ester (2.3 grams, 10.1 [MMOL)] in tetrahydrofuran (50 ml) was added 4- fluoro phenol (1.75 grams, 15.6 mmol), triphenyl phosphine (4.02 grams, 15.3 [MMOL)] and diethyl azidocarboxylate (2.4 [ML,] 15.2 [MMOL).] The reaction was stirred at ambient temperature overnight. The reaction was concentrated in vacuo and chromatagraphed on silica gel to give the title compound (2.38 grams, 73 % [YIELD).,]

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; PFIZER PRODUCTS INC.; WO2004/9588; (2004); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 98-64-6, 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. 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.

General procedure: The prepared TfOH-SiO2 (60 mg, containing 0.05 mmol TfOH) was added to the toluene (2 mL) solution of alkene (2 mmol or 4 mmol) and sulfonamide (1 mmol) and the reaction mixture was stirred at 70 oC (or 85 oC). The course of the reaction was monitored by TLC. After the completion of the reaction, the mixture was cooled to room temperature and the reactor was centrifuged (2000 r/min) for 2 min and the solution was removed by syringe. The catalyst was then washed with toluene (1 mL) twice with the same procedure and a new reaction was carried out by adding the new batch of alkene (2 mmol), sulfonamide (1 mmol) and toluene (2 mL) to the recovered catalyst. The solution containing the product was purified through a silica gel flash column to afford the product.

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-Chlorobenzenesulfonamide, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Liu, Pei Nian; Xia, Fei; Zhao, Zheng Le; Wang, Qing Wei; Ren, Yu Jie; Tetrahedron Letters; vol. 52; 46; (2011); p. 6113 – 6117;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics