Month: March 2021

Application of 113778-69-1, 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. 113778-69-1, name is N-Methoxy-N-methylisobutyramide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

n-Butyllithium (2.5 M in n-hexane, 22.0 mL, 44.4 mmol) was added dropwise to a – 80 C solution of 2-bromo-5-(trifluoromethyl)pyridine (5.0 g, 22.1 mmol) in THF (35 mL), and the resulting solution stirred for 10 minutes. N-methoxy-N-methylisobutyramide (3.49 g, 26.61 mmol) was added at -80 C, and the reaction mixture stirred for 1 h at -80 C. The reaction was then quenched by the addition of 40 mL of saturated aqueous ammonium chloride solution, and the mixture was allowed to warm to room temperature. The resulting solution was extracted with 3×40 mL of ethyl acetate, and the combined organic phases were washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum. The residue was purified via column chromatography on silica gel (eluting with 1 :7 ethyl acetate/petroleum ether) to give 2-methyl-l-(5-(trifluoromethyl)pyridin-2-yl)propan-l-one (550 mg, 8% yield) as a yellow solid. MS (ESI, m/z): 218 [M+H]+.

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, N-Methoxy-N-methylisobutyramide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; FORMA THERAPEUTICS, INC.; ZHENG, Xiaozhang; MARTIN, Matthew W.; NG, Pui Yee; THOMASON, Jennifer R.; HAN, Bingsong; RUDNITSKAYA, Aleksandra; LANCIA, JR., David R.; (180 pag.)WO2019/204550; (2019); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 956434-30-3, A common heterocyclic compound, 956434-30-3, name is tert-Butyl 8-chloro-2,3-dihydropyrido[3,2-f][1,4]oxazepine-4(5H)-carboxylate, molecular formula is C13H17ClN2O3, 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 1) To a solution of 1-cyclopentylethanol (0.22 mL) in toluene (4 mL) was added sodium hydride (0.14 g), and the resulting mixture was stirred at 100C for 15 min under a nitrogen atmosphere. A mixture of tert-butyl 8-chloro-2,3-dihydropyrido[3,2-f][1,4]oxazepine-4(5H)-carboxylate (0.50 g), BINAP (0.033 g), Pd2(dba)3 (0.024 g) and toluene (4 mL) was added, and the resulting mixture was stirred at 100C for 2 hr under an argon atmosphere. The reaction solution was poured into water, and the resulting product was extracted with ethyl acetate. The organic layer was washed with water and saturated brine and dried, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (solvent gradient; 0?40% ethyl acetate/hexane) to give tert-butyl 8-(l-cyclopentylethoxy)-2,3-dihydropyrido[3,2-f][1,4]oxazepine-4(5H)-carboxylate (0.45 g, 70%) as a white powder. 1H-NMR(CDCl3):delta1.27(3H,t,J=6.0Hz), 1.25-1.85(8H,m), 1.43(9H,s), 2.00-2.12(1H,m), 3.80-3.82(2H,m), 4.21(2H,brs), 4.33-4.45(2H,m), 5.01(1H,brs), 6.38(1H,d,J=8.1Hz), 7.30-7.50(1H,m)

The synthetic route of 956434-30-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP2213675; (2010); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 598-55-0, 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. 598-55-0, name is Methyl carbamate, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a well-ground mixture of beta-naphthol (0.288 g, 2 mmol), aldehyde (2 mmol) and amide derivatives (2.4 mmol) in a 10 mL round-bottomed flask connected to a reflux condenser, was added TrCl (0.055 g, 0.2 mmol), and the resulting mixture was stirred in an oil-bath (70 C) for the times reported in Table 2. Afterward, petroleum ether (20 mL) was added to the reaction mixture, refluxed, and stirred for 3 min, and filtered (TrCl is soluble in petroleum ether; however, the products are insoluble in this solvent). The filtrate containing the catalyst was washed two times with 20 mL of 40% (w/v) solution of NaHSO3 in H2O/EtOH (4:1) to extract the unreacted aldehyde dissolved in the petroleum ether. The organic layer was separated and dried with CaCl2; the solvent was evaporated to give pure recycled TrCl. The solid residue was recrystallized from EtOH (95%) to give the pure product (compounds 1a-m, 2a-d, and 3a-e).

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

Reference:
Article; Khazaei, Ardeshir; Zolfigol, Mohammad Ali; Moosavi-Zare, Ahmad Reza; Abi, Fereshteh; Zare, Abdolkarim; Kaveh, Hamideh; Khakyzadeh, Vahid; Kazem-Rostami, Masoud; Parhami, Abolfath; Torabi-Monfared, Hossein; Tetrahedron; vol. 69; 1; (2013); p. 212 – 218;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 6973-09-7, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 6973-09-7 name is 5-Amino-2-methylbenzenesulfonamide, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Example 60: Process for the preparation of PZP.HCI[000177] A 250 mL reactor equipped with a mechanical stirrer was charged with CPM I (4.84 g, 16.82 mmol), AMBS (3.29 g, 17.66 mmol, 1 .05 eq) and 90% acetic acid (29 mL, 6V) and the reaction mixture was heated to 55 C with stirring, leading to dissolution. After 3.5 h precipitation commenced and the reaction was continue for 22 h in total. The resulting mixture was then heated to 65 C over 0.5 h and stirring was continued at the same temperature for an additional 5 h. The reaction mixture was then heated to 100 C over 1 h leading to complete dissolution. Stirring was continued at the same temperature for 0.5 h and then EtOH abs. (48 mL, 10V) was added drop-wise with concomitant cooling to 80 C over a period of 0.5 h. The mixture was then cooled to 0 C over a period of 4 h and stirring was continued at the same temperature for 16 h. The solids were filtered and the filter cake was washed with EtOH abs. (4x 14.5 mL, 4×3 V) at Patent ApplicationAtty Docket No. 14669.0172 WOU 1 room temperature and dried in a vacuum oven (35 mbar) at 60 C for 22 h to give pure PZP.HC1 (7.05 g, 88.5% yield, 99.4% assay, 99.9% purity, 7.32% CI, CPMI < 20 ppm) as a beige powder. At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Amino-2-methylbenzenesulfonamide, and friends who are interested can also refer to it. Reference:
Patent; TEVA PHARMACEUTICAL INDUSTRIES LTD.; TEVA PHARMACEUTICALS USA, INC.; RENDELL, Jacob; KWOKAL, Ana; WO2011/69053; (2011); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

55512-05-5, name is 3-(Methylsulfonamido)benzaldehyde, 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. Recommanded Product: 55512-05-5

N-(3-formylphenyl)methanesulfonamide (465 mg, 2.33 mmol) was dissolved in acetone (10 mL) at room temperature. Powdered K2C03 (968 mg, 7.00 mmol) and iodomethane (0.29 mL, 4.67 mmol) were then added and the reaction mixture allowed to stir overnight. The reaction mixture was poured into water (5 mL) and extracted with EtOAc (3 x 15 mL). The combined organic phases were washed with brine (5 mL),dried over MgSO4 and concentrated to give crude product which was carried on without further purification.

The synthetic route of 55512-05-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GILEAD SCIENCES, INC.; BACON, Elizabeth, M.; BALAN, Gayatri; CHOU, Chien-hung; CLARK, Christopher, T.; COTTELL, Jeromy, J.; KIM, Musong; KIRSCHBERG, Thorsten, A.; LINK, John, O.; PHILLIPS, Gary; SCHROEDER, Scott, D.; SQUIRES, Neil, H.; STEVENS, Kirk, L.; TAYLOR, James, G.; WATKINS, William, J.; WRIGHT, Nathan, E.; ZIPFEL, Sheila, M.; (640 pag.)WO2017/7694; (2017); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 147291-66-5, name is tert-Butyl 3-aminobenzylcarbamate, 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 147291-66-5, name: tert-Butyl 3-aminobenzylcarbamate

2-chloro-ethyl[3-(tert-butoxycarbonylamino-methyl)-phenyl]-carbamate 900 mg g (3.48 mmol) tert-butyl 3-amino-benzyl)-carbamate are liberated as the base, then placed in 40 ml of tetrahydrofuran, and 1.11 ml (8 mmol) triethylamine and 0.75 ml (6.82 mmol) 2-chloroethylchloroformate are added. The reaction mixture is stirred for 16 hours at ambient temperature, then extracted with dichloromethane and water. The organic phase is separated off using a phase separation cartridge and evaporated to dryness. Yield: 1.20 g (100% of theoretical)

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

Reference:
Patent; Brandl, Trixi; Maier, Udo; Hoenke, Christoph; Joergensen, Anne T.; Pautsch, Alexander; Breitfelder, Steffen; Grauert, Matthias; Hoffmann, Matthias; Scheuerer, Stefan; Erb, Klaus; Pieper, Michael; Pragst, Ingo; US2007/238746; (2007); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Related Products of 239074-29-4,Some common heterocyclic compound, 239074-29-4, name is tert-Butyl (trans-4-(hydroxymethyl)cyclohexyl)carbamate, molecular formula is C12H23NO3, 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.

Alcohol (79.5 g, 347 mmol) was dissolved in tetrahydrofuran (800 ml). Triethylamine (72.5 ml, 520 mmol) and methanesulfonyl chloride (32.2 ml, 416 mmol) were sequentially added thereto under ice-cooling with stirring and the mixture was reacted for 1.5 hour. The reactant was poured into aqueous citric acid (citric acid monohydrate 30 g in water 500 ml) to become pH 4 and extracted with ethyl acetate. The organic layer was washed with water and dried over magnesium sulfate anhydrous. The solvent was removed under reduced pressure. The crystal deposited in the removal process was collected by filtration and washed with hexane to give mesylate (100 g). The obtained mesylate was dissolved in dimethylformamide (100 ml) and sodium azide (63.7 g, 980 mmol) was added thereto and reacted at 80 C. for 2 hours. The reactant was poured into water and extracted with ethyl acetate. The organic layer was washed with water and dried over magnesium sulfate anhydrous. The solvent was removed under reduced pressure to quantitatively give the desired Azide (the crude weight is 85.4 g).1H-NMR (DMSO-d6) delta ppm: 0.90-1.21 (m, 4H), 1.32-1.50 (m, 1H), 1.37 (s, 9H), 1.65-1.84 (m, 4H), 3.06-3.24 (m, 3H), 6.71 (d, 1H, J=8.1 Hz).

The synthetic route of 239074-29-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shionogi & Co., Ltd.; US2010/273841; (2010); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 226260-01-1, 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. 226260-01-1, name is 3-Fluoro-N-methoxy-N-methylbenzamide, This compound has unique chemical properties. The synthetic route is as follows.

Example 5 1-(3-FLUOROPHENYL) BUTAN-1-ONE To a solution of 3-fluoro-N-methoxy-N-methylbenzamide (130 mg, 0.71 mmol) in dry THF (2 mL) cooled to-10 C was added propyl magnesium chloride (532 ul, 2M solution in ether, 1.1 mmol) under nitrogen. The solution was stirred at-10 C for Ih and at room temperature for 75 min. The solution was the poured into saturated aqueous ammonium chloride and the product extracted into ethyl acetate (3 x 25 mL). The organic layers were combined, washed with brine, dried (MGSO4) and concentrated to give a pale yellow oil, which was purified by chromatography using ethyl acetate-hexane (1: 9) to separate the pure product (78 mg, 66%). ‘H-N. m. r. (CDCl3) No. 1.01 (t, =7. 4Hz, 3H, Me), 1.77 (sep, 2H, CH2CH3), 2.93 (T, J=7. 2Hz, 2H, COCH2), 7.15-7. 30 (m, 1H, Ar), 7.35-7. 50 (m, 1H, Ar), 7.60-7. 70 (m, 1H, Ar), 7.70-7. 80 (m, 1H, Ar.

The chemical industry reduces the impact on the environment during synthesis 3-Fluoro-N-methoxy-N-methylbenzamide. I believe this compound will play a more active role in future production and life.

Reference:
Patent; CYTOPIA PTY LTD; WO2004/52868; (2004); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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 6228-73-5 as follows. Quality Control of Cyclopropanecarboxamide

Cyclopropanecarboxamide (22.5 mg, 0.26 mmol) was combined with Int3 (30 mg, 0.088 mmol). Dimethylacetamide (DMA, 0.6 mL) was added to the vessel, followed by the addition of tris (diphenylmethyleneacetone) dicum (0) (Pd2dba3, 8.1 mg, 0.0088 mmol)4,5-bis (diphenylphosphino) -9,9-dimethyl(Xantphos, 10 mg, 0.018 mmol) and cesium carbonate (115 mg, 0.35 mmol). The vessel was then evacuated and backfilled three times with nitrogen and heated to 145 & lt; 0 & gt; C for 1 hour.The reaction was cooled to room temperature and then diluted with ethyl acetate (EtOAc, ca. 250 mL). The solution was washed twice with water, dried over sodium sulfate (Na2SO4), filtered, concentrated and purified using preparative HPLC. The product in the form of TFA salt was collected and then dissolved in about 15 mL of water, to which about 100 mL of saturated sodium bicarbonate (NaHCO3, an aqueous solution) was added and stirred for 10 minutes. The product of (x3) was extracted from the slurry using dichloromethane (DCM), dried over sodium sulfate, filtered, concentrated and collected to give 16.3 mg of 1 (48% yield).

According to the analysis of related databases, 6228-73-5, the application of this compound in the production field has become more and more popular.

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; (124 pag.)TWI582077; (2017); B;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 83948-53-2, A common heterocyclic compound, 83948-53-2, name is tert-Butyl N-(3-Bromopropyl)carbamate, molecular formula is C8H16BrNO2, 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.

Sodium carbonate (5.65 g, 40.9 mmol) was added to a solution of 4-iodophenol 5 (3.00 g, 13.6 mmol) in anhydrous acetonitrile (100 mL). The reaction was refluxed for 1 hour and the bromo derivative 4 (2.60 g, 10.9 mmol) was then added to this suspension. The reaction mixture was refluxed for 12 hours. The reaction progress was monitored by TLC. After this period, the reaction was complete. The reaction mixture was cooled to room temperature and the solvent was removed under reduced pressure. Water (100 mL) was added to this residue, and the mixture was extracted with dichloromethane (2¡Á50 mL). The organic phases were combined, dried over sodium sulfate and filtered. The solvent was removed under reduced pressure and the residue was purified by chromatography on a column of silica (dichloromethane) to give compound 6b in the form of a white solid (3.10 g, 75%). m.p.: 79-80 C. 1H NMR (500 MHz, CDCl3) delta: 7.52 (d, J=8.9 Hz, 2H), 6.64 (d, J=8.9 Hz, 2H), 4.69 (s, 1H), 3.95 (t, J=6.2 Hz, 2H), 3.29 (td, J=6.2; 6.2 Hz, 2H), 1.94 (m, J=6.2 Hz, 2H), 1.41 (s, 9H), 13C NMR (125 MHz, CDCl3) delta: 158.7; 155.9; 138.2; 116.9; 82.9; 65.9; 37.9. HMRS (ESI) calculated for C14H20NO31 [M+H+], m/z 378.0561. found: 378.0559.

The synthetic route of 83948-53-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CISBIO BIOASSAYS; CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE; ECOLE NORMALE SUPERIEURE DE LYON; Lamarque, Laurent; Maury, Olivier; Parker, David; Zwier, Jurriaan; Walton, James W.; Bourdolle, Adrien; US2014/336373; (2014); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics