Month: September 2021

Related Products of 49834-22-2,Some common heterocyclic compound, 49834-22-2, name is 3-Bromo-N-methylbenzamide, molecular formula is C8H8BrNO, 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.

[0121] In a dry 50 mL round bottom flask, 2-chloro-5-methyl-pyrirnidin-4-ylamine (0.3 g, 2.09 mmol, 1 equiv), 3-bromo-N-methyl-benzamide (0.489g, 2.29 mmol, 1.1 equiv), cesium carbonate (2.04.g, 6.27 mmol, 3 equiv), 4,5-bis(diphenylphosphino)-9,9-dimethyl xanthene (0.242 g, 0.418 mmol, 0.2 equiv) and tris(dibenzylideneacetone) dipalladium (0.191 g, 0.209 mmol, 0.1 equiv) were combined. Reactants were diluted with dioxane (20 mL), flushed with argon and outfitted with reflux condenser. Reaction was heated to reflux for 16 hours. Reaction was then transferred into centrifuge tube, spun down, decanted and evaporated. Resulting yellow solids were diluted with DCM and adsorbed onto silica gel. Chromatography (gradient of 50% ethyl acetate in hexanes up to 100% ethyl acetate) afforded the title intermediate 17 as a pale yellow powder (0.25 g, 43% yield). MS (ESI+): 277.01 (M+H), r.t. = 1.92 min.

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

Reference:
Patent; TARGEGEN, INC.; WO2007/53452; (2007); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Related Products of 60144-53-8, 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. 60144-53-8, name is tert-Butyl (4-fluorophenyl)carbamate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

(4-Fluoro-phenyl)-carbamic acid terf-butyl ester (2.1 1 g, 10.0 mmol, ABCR, Karlsruhe, Germany) was added to a round bottom and purged with nitrogen. Anhydrous tetrhydrofuran (200 mL) was added to dissolve the solids and the flask placed in a dry ice / acetone bath (internal temperature -74 C uncorrected). terf-Butyl lithium (1 .7 M in pentane, 14.2 mL, 24.0 mmol) was added over 5 min causing a yellow color to develop. After the addition was complete the reaction was stirred in a -20 C bath for 1 h. At this point, 3-ethoxymethacrolein (1.43 mL, 12.0 mmol) was added dropwise over 5 min, keeping the temperature below -19 C. The reaction was stirred at -20 C for 2 h before slowly adding trifluoroacetic acid (14 mL) over 5 min. The red solution was stirred at room temperature for 16 h before bring to pH 12 with 1 N NaOH. This was extracted twice with ethyl acetate and the combined organics dried over MgS04. Purification by silica gel flash chromatography (ethyle acetate / heptanes) gave impure desired material. This was extracted into three portions of 1 N HCI, the combined aqueous layers were brought to pH 12 with 6 N NaOH, and then extracted into two portions of ethyl acetate. The combined organics were dried over MgS04 and concentrated in vacuo to give 6-fluoro-3-methyl-quinoline (48.0 mg) as an orange oil. 1 H NMR (400 MHz, CDCI3) delta 8.74 (s, 1 H) 8.07 (dd, J=9.1 , 5.4 Hz, 1 H) 7.88 (s, 1 H) 7.33 – 7.46 (m, 2 H) 2.53 (s, 3 H); MS (M+1 ): 162.1 .

The synthetic route of tert-Butyl (4-fluorophenyl)carbamate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER INC.; DIDIUK, Mary; FILIPSKI, Kevin J.; GUZMAN-PEREZ, Angel; LEE, Esther C.; PFEFFERKORN, Jeffrey A.; STEVENS, Benjamin; TU, Meihua; WO2013/14569; (2013); 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. 102562-86-7, name is 3-(Aminomethyl)benzamide, A new synthetic method of this compound is introduced below., Recommanded Product: 3-(Aminomethyl)benzamide

To a solution of Intermediate 1h (50 mg, 0.152 mmol) and 3-aminomethyl-benzamide (60 mg, 0.228 mmol) in 2 mL DMF, were added iPr2Net (106 muL, 0.608 mmol), HOAT (41.4 mg, 0.304 mmol) and EDCI (35 mg, 0.182 mmol). The mixture was stirred at rt for 14 h, then was diluted with EtOAc. The organic phase was washed with H2O, 1N HCl, H2O, 0.1 N, NaOH, and brine, dried (Na2SO4), and concentrated. The crude product was recrystallized from methanol to afford 7.2 mg (10%) of Example 24. MS (HR-ESI) calculated for C24H24N5O5 (M+H+), found 462.1787; MS (ESI) 462.3 (M+H+), 484.3 (M+Na+); 1H NMR (300 MHz, CD3OD) delta. 8.51 (br. S, 1H), 7.84 (s, 1H), 7.78 (d, J=7.7, 1H), 7.53-7.31 (m, 7H), 5.20 (s, 2H), 5.13 (dd, J=3.0, 1.0, 1H), 4.61-4.37 (m, 2H), 3.25-3.16 (m, 1H), 3.12-3.03 (m, 1H), 2.66-2.55 (m, 1H), 2.32-2.24 (m, 1H).

The synthetic route of 102562-86-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Glunz, Peter W.; US2004/6065; (2004); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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. 239074-29-4, name is tert-Butyl (trans-4-(hydroxymethyl)cyclohexyl)carbamate, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: tert-Butyl (trans-4-(hydroxymethyl)cyclohexyl)carbamate

b) ((1r,4r)-4-(tert-Butoxycarbonylamino)cyclohexyl)methyl 4-methylbenzene-sulfonate A solution of 4-methylbenzene-1-sulfonyl chloride (2.28 g, 11.96 mmol) in dichloromethane was added to a solution of tert-butyl (1r,4r)-4-(hydroxymethyl)cyclohexylcarbamate (Preparation 50a, 2.11 g, 9.2 mmol) and triethylamine (1.59 mL, 11.4 mmol) in dichloromethane (50 mL) and the mixture was stirred overnight at room temperature. The mixture was washed with 1 M aqueous sodium hydroxide solution and the organic layer was dried (MgSO4) evaporated and the residue was purified by flash chromatography (diethyl ether/hexanes) to give the title compound (2.91 g, 83%) as a white solid. LRMS (m/z): 382 (M-H)+.1 H NMR (300 MHz, CDCl3) delta ppm 0.90 – 1.12 (m, 4H), 1.43 (s, 3H), 1.78 (dd, 2H), 1.99 (d, 2H), 3.34 (m, 1H), 3.46 (t, 1H), 3.81 (d, 2H), 4.37 (m, 1H), 7.34 (d, 2H), 7.77 (d, 2H).

According to the analysis of related databases, 239074-29-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ALMIRALL, S.A.; EASTWOOD, Paul Robert; GONZALEZ RODRIGUEZ, Jacob; GOMEZ CASTILLO, Elena; BACH TANA, Jordi; WO2011/157397; (2011); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Related Products of 113778-69-1,Some common heterocyclic compound, 113778-69-1, name is N-Methoxy-N-methylisobutyramide, molecular formula is C6H13NO2, 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 stirred suspension of 1,1-dimethylethyl (3-methyl-2-pyridinyl)carbamate (3Og, 144mmol) in tetrahydrofuran (30OmL) at O0C under an atmosphere of nitrogen was added n-butyl-lithium (2.3M, 123mL) over 90 mins. After 30 mins at O0C lambda/,2-dimethyl-/V- (methyloxy)propanamide (22.7g, 173mmol) was added. After a further 60 mins at O0C the reaction was allowed to warm to ambient temperature and was added to 5M aqueous hydrochloric acid (30OmL) and heated to 600C for 1.5 h. The organic was separated. The aqueous was basified with 10M aqueous sodium hydroxide and extracted with ethyl acetate. The combined extracts were dried (MgSO4) and concentrated in vacuo to give the title compound as an orange crystalline solid (22.04g, 95%). LCMS rt = 2.38mins, MH+= 161

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

Reference:
Patent; GLAXO GROUP LIMITED; WO2008/34860; (2008); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 127-77-5, A common heterocyclic compound, 127-77-5, name is 4-Amino-N-phenylbenzenesulfonamide, molecular formula is C12H12N2O2S, 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.

General procedure: N1,N3-bis(4-(N-(5-methylisoxazol-3-yl)sulfamoyl)phenyl)malonamide (1). 5f (253 mg, 1 mmol) was dissolved in the solutionof THF (10 mL) and pyridine (1 mL) before 2a (240 mg, 2 mmol)wasdropwise added. Then the reaction mixture was stirred at roomtemperature overnight until the white solid was precipitated. Thecrude product was filtered and recrystallized with ethanol to give a1 as a light-yellow solid, yield 72%

The synthetic route of 127-77-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wang, Lei; Li, Li; Zhou, Zi-Han; Jiang, Zheng-Yu; You, Qi-Dong; Xu, Xiao-Li; European Journal of Medicinal Chemistry; vol. 136; (2017); p. 63 – 73;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 1314538-55-0, 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 1314538-55-0 as follows.

[01253] A mixture of 4-chloro-2-cyclopropyl-6-(trifluoromethyl)pyrimidine (500 mg, 2.25 mmol, 1.00 equiv), potassium tert-butyl N-[(trifluoroboranuidyl)methyl]carbamate (600 mg, 2.53 mmol, 1.13 equiv), Pd(PPh3)2C12 (150 mg, 0.21 mmol, 0.01 equiv), and sodium carbonate (750 mg, 7.07 mmol, 3.15 equiv) in ethanol (20 mL)/water(2 mL) was stirred for 3 hours at 80C under nitrogen. The resulting mixture was concentrated under vacuum. The residue was purified by a silica gel colunm eluting with ethyl acetate/petroleum ether (1/4) to afford the title compound (250 mg, 35%) as greenish oil. LCMS [M+H] 318.

According to the analysis of related databases, 1314538-55-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; ESTRADA, Anthony; VOLGRAF, Matthew; CHEN, Huifen; KOLESNIKOV, Aleksandr; VILLEMURE, Elisia; VERMA, Vishal; WANG, Lan; SHORE, Daniel; DO, Steven; YUEN, Po-wai; HU, Baihua; WU, Guosheng; LIN, Xingyu; LU, Aijun; (537 pag.)WO2016/128529; (2016); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 631-58-3, 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. 631-58-3, name is Propanethioamide, This compound has unique chemical properties. The synthetic route is as follows.

Reference Example 28 4-[2-ethyl-4-(3-methylphenyl)-1,3-thiazol-5-yl]-2-pyridylamine A solution of 2-(2-amino-4-pyridyl)-2-bromo-1-(3-methylphenyl)ethanone hydrobromide (125 g, 0.323 mol) and thiopropionamide (28g, 0.314 mol) in N,N-dimethylformamide (1200 mL) was stirred at room temperature for 14 hrs. The solvent was evaporated under reduced pressure. Aqueous sodium hydrogen carbonate solution was poured into the residue and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogen carbonate solution, dried and concentrated. Crude crystals were washed with hexane-ethyl acetate = 1: 1 to give the title compound (76.0 g, yield 82%). melting point: 144-146C.

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

Reference:
Patent; Takeda Chemical Industries, Ltd.; EP1364949; (2003); 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. 153248-46-5, name is [1-[(Boc-amino)methyl]cyclopropyl]methanol, A new synthetic method of this compound is introduced below., Recommanded Product: 153248-46-5

Step 3: Synthesis of diethyl l-[(l-{[(tert- butoxycarbonyl)amino]methyl}cyclopropyl)methyl]-1H-indole-2,6-dicarboxylateTo a solution of tert-butyl { [l-(hydroxymethyl)cyclopropyl]methyl}carbamate (20 g, 99.5 mmol), diethyl 1H-indole-2,6-dicarboxylate (26 g, 99.5 mmol) and triphenylphosphine (52 g, 199 mmol) in THF (300 mL) is added diisopropyl azodicarboxylate (31 mL, 199 mmol) at room temperature. The reaction mixture is stirred for 60 h and the solvent is evaporated. The residue is purified by flash column chromatography using 12% EtOAc in petroleum ether to afford a mixture of diethyl 1- [(l-{ [(tert-butoxycarbonyl)amino]methyl}cyclopropyl)methyl]-1H-indole-2,6- dicarboxylate and diethyl 1H-indole-2,6-dicarboxylate (36 g) as a white solid. The mixture is used in the next step without further purification.

The synthetic route of 153248-46-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BOYER, Stephen, James; GAO, Donghong, Amy; GUO, Xin; KIRRANE, Thomas, Martin, Jr.; SARKO, Christopher, Ronald; SNOW, Roger, John; SOLEYMANZADEH, Fariba; ZHANG, Yunlong; WO2011/71716; (2011); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 6228-73-5,Some common heterocyclic compound, 6228-73-5, name is Cyclopropanecarboxamide, molecular formula is C4H7NO, 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 3 To a reaction vial was added the product from Step 2 (20 mg, 0.056 mmol), cyclopropanecarboxamide (4.74 mg, 0.056 mmol) and BrettPhos (3.59 mg, 6.69 muiotaetaomicron) and the contents were purged with nitrogen before adding DMA (0.10 mL) and dioxane (0.20 mL). The resulting slurry was sparged with nitrogen for an additional minute, then Pd2(dba)3 (5.10 mg, 5.57 muiotaetaomicron) followed by LiHMDS (1 M in THF) (0.139 mL, 0.139 mmol) was added and the reaction vial was capped under nitrogen and placed into a preheated 110 C heating block and the mixture was allowed to stir at that temperature for 1.5h. After cooling, the reaction was quenched with MeOH, concentrated to remove the volatiles, and was purified by reverse phase preparative LCMS with the following conditions: Column: Waters XBridge C18, 19 x 200 mm, 5-muiotaeta particles; Mobile Phase A: 5:95 acetonitrile: water with 0.1% trifluoroacetic acid; Mobile Phase B: 95:5 acetonitrile: water with 0.1% trifluoroacetic acid; Gradient: 0-100% B over 20 minutes, then a 5-minute hold at 100% B; Flow: 20 mL/min. Fractions containing the desired product were combined and dried via centrifugal evaporation. The yield of the product (Example 29) was 15.4 mg (49%). HPLC (Method E) RT = 0.98 min. HPLC (Method G) RT = 0.76 min. LCMS observed MH+ = 408.2. 1H NMR (500MHz, DMSO-d6) delta 11.11 (br. s., 1H), 10.82 (br. s., 1H), 8.79 (br. s., 1H), 8.49 (s, 1H), 7.75 (d, J=6.7 Hz, 1H), 7.54 (d, J=7.9 Hz, 1H), 7.38 – 7.27 (m, 1H), 3.69 (s, 3H), 2.81 (d, J=4.3 Hz, 3H), 1.91 (br. s., 1H), 0.90 – 0.78 (m, 4H).

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

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; MOSLIN, Ryan M.; WEINSTEIN, David S.; WROBLESKI, Stephen T.; ZHANG, Yanlei; TOKARSKI, John S.; MERTZMAN, Michael E.; LIU, Chunjian; WO2015/69310; (2015); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics