Category: amides-buliding-blocks

Synthetic Route of 123986-64-1, These common heterocyclic compound, 123986-64-1, name is tert-Butyl 4-(hydroxymethyl)benzylcarbamate, 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.

1) Synthesis of 1-[4-[N-(tert-butoxycarbonyl)aminomethyl]benzyl]-4-benzylpiperidine To a solution of 5.0 g (21.07 mM) of 4-[N-(tert-butoxycarbonyl)aminomethyl]-1-phenylmethanol and 5.9 ml (42.33 mM) of triethylamine in THF (42 ml) was added 2.5 ml (32.3 mM) of methanesulfonyl chloride at 0 C. and the mixture was stirred at the prevailing temperature for one hour. The reaction was stopped by adding saturated aqueous solution of sodium hydrogen carbonate and the reaction mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated aqueous solution of sodium chloride and dried over MgSO4. The solvent was then distilled off under reduced pressure to provide 7.21 g (21.07 mM) of crude product as light-brown solid. To a solution of 7.21 g (21.07 mM) of this crude mesylate in ethanol (42 ml) was added 5.9 g (42.33 mM) of triethylamine as well as 3.69 g (21.05 mM) of 4-phenylpiperidine and the mixture was refluxed for 18 hours. After cooling to room temperature, the reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with water and saturated aqueous solution of sodium chloride and dried over MgSO4. After concentration, the crude product was purified by column chromatography (ethyl acetate-hexane: 50%) to provide the title compound as light-yellow oil. Yield 5.77 g (69%) 1H-NMR (200 MHz, CDCl3) delta: 1.20-1.40 (2H, m), 1.46 (9H, s), 1.85-2.01 (2H, m), 2.53 (2H, d, J=6.2 Hz), 2.78-2.93 (2H, m), 3.48 (2H, s), 4.29 (2H, d, J=6.0 Hz), 4.70-4.88 (1H, m), 7.07-7.34 (9H, m). IR (neat): 3350, 2924, 1709, 1508, 1452, 1365, 1252, 1173 cm-1.

The synthetic route of 123986-64-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Chemical Industries, Ltd.; US6235731; (2001); B1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 193751-54-1, 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 193751-54-1 as follows.

To a solution of N-l-Boc-amino-3-cyclopentene (1.94 g, 10.58 mmol) in a mixture of acetone (63 mL)/water (7.8 mL) (8: 1) at room temperature was added N-methyl morpholine N-oxide (2.48 g, 21.16 mmol). After 2 minutes osmium tetroxide (4% in water) (3.37 mL) was added and the resulting mixture stirred at room temperature for 23h. The reaction mixture was then quenched by the addition of aqueous Na2S203 (0.2 M, 25 mL) and extracted with CH2C12 (2 x 50 mL). The combined organic extracts were washed with aqueous Na2S203 (0.2 M, 10 mL), dried (MgS04), filtered and evaporated in vacuo. The crude material was purified by flash chromatography eluting with EtOAc (17 – 100 %) in heptane to give a mixture of the title compounds as a yellow solid (1.31g, 57 %).

According to the analysis of related databases, 193751-54-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; BROMIDGE, Steven; BURCH, Jason; HEIFETZ, Alexander; KRULLE, Thomas; MONTALBETTI, Christian A.G.N.; PEI, Zhonghua; PEREZ-FUERTES, Yolanda; TRANI, Giancarlo; (223 pag.)WO2016/1341; (2016); A1;,
Amide – Wikipedia,
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Synthetic Route of 154350-29-5, 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. 154350-29-5, name is Cyclopropanesulfonamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Step 7: Synthesis of (IS, 4R, 6S, 14S, 18R)- [7-cis-4-Cyclopropanesulfonylaminocarbonyl-12-cyclopropyl-18-(tert-butyldimethylsilyloxy)- 2, 15-dioxo-3, 12,16-triaza-tricyclo[14.3.0. (f’6]nonadec-7 -en-14-yl] carbamic acid, tert-butyl ester.; (15, AR, 65, 145, 18R)-7-c-14-tert-Butoxycarbonylamino-18-(tert- butyldimethylsilyloxy)-2,15-dioxo-3, 12,16-triazatricyclo[ 14.3.0.04’6]nonadec-7-ene- 4-carboxylic acid (490 mg, 0.79 mmol) was dissolved in 15 mL of THF and treated with CDI (179 mg, 1.10 mmoL). (Care was taken to avoid moisture by using oven dried glassware and maintaining a dry N2 atmosphere.) After refluxing the reaction mixture for two hours, it was cooled to rt and treated sequentially with cyclopropylsulfonamide (134 mg, 1.10 mmoL) and DBU (168 mg, 1.10 mmoL). After stirring overnight at rt, the THF was removed by rotary evaporation. The residue was dissolved in water and IN HCl was added until the pH = 5. This aqueous solution was extracted with EtOAc (3x). The combined EtOAc extracts were dried (MgSO4) and concentrated in vacuo to give the crude product. Purification by flash column, eluting with 3percent methanol in methylene chloride, gave 300 mg (53percent) Of (IS”, 4R, 65, 145, 18R)- [7-c-4-Cyclopropanesulfonylaminocarbonyl-12- cyclopropyl- 18-(tert-butyldimethylsilyloxy)-2, 15 -dioxo-3 ,12,16-triaza- tricyclo[14.3.0.04’6]nonadec-7-en-14-yl]carbamic acid, tert-butyl ester as a white solid: LC-MS (Phenomenex 10 mum Cl 8 HPLC column: 3.0×50 mm length. Gradient: 100percent Solvent A/0percent Solvent B to 0percent Solvent A/100percent Solvent B. Gradient time: 2 min. Hold time: 1 min. Flow rate: 5 mL/min. Detector Wavelength: 220 nM. Solvent A: 10percent MeOH / 90percent H2O / 0.1percent TFA. Solvent B: 10percent H2O / 90percent MeOH / 0.1percent TFA.) (Retention time: 2.40 min), MS m/z 724 (M++l).

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

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2008/64061; (2008); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 598-55-0, 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. 598-55-0, name is Methyl carbamate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To a mixture of 2-naphthol(5 mmol), an aldehyde (5 mmol), and a carbamate(5.5 mmol), CuCl2·2H2O (0.05 mmol) was added. Thereaction mixture was stirred on a preheated water bathat 70C. After completion of the reaction (monitoredby TLC), the reaction mixture was cooled to RT.washed with H2O/EtOH (v/v = 1/1), and recrystallizedfrom H2O/EtOH (v/v = 2/3). The products were characterized by IR, 1H NMR, 13C NMR, LC/MS andelemental analysis.

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, Methyl carbamate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Song, Zhiguo; Liu, Lianli; Sun, Xiaohu; Cui, Yan; Indian Journal of Chemistry – Section B Organic and Medicinal Chemistry; vol. 53; 6; (2014); p. 740 – 745;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 122334-37-6, 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. 122334-37-6, name is 4-Chloro-N-methoxy-N-methylbenzamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Preparation 2.2 6-(4-Chlorophenyl)-4-hydroxy-5-methyl-2H-pyran-2-one (IX) A suspension of 4.7 g of sodium hydride at 60% in oil, in 100 ml of THF, is cooled to 0 C. under a nitrogen atmosphere, a solution of 17 g of ethyl 3-oxopentanoate in 100 ml of THF is then added slowly, and the mixture is left to stir at 0 C. for 5 minutes. 86.5 ml of a 1.5 M solution of lithium diisopropylamide mono(tetrahydrofuran) in cyclohexane is then added dropwise at 0 C., and the mixture is left to stir at 0 C. for 20 minutes. Finally, a solution of 23.5 g of the compound of Preparation 1.2 in 50 ml of THF is added slowly and the mixture is left to stir while allowing the temperature to return to AT, and stirred overnight at AT. A mixture of ice/HCl at 10% is added, the reaction mixture is extracted with EtOAc, the organic phase is dried over Na2SO4, and the solvent is evaporated off under vacuum. The residue is taken up with 150 ml of concentrated H2SO4 and the mixture is left to stir at AT for 3 hours. The reaction mixture is poured onto ice and left to stir, and the precipitate formed is spin-filter-dried and washed with iso ether and then with pentane. 25 g of the expected compound are obtained after drying.

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-Chloro-N-methoxy-N-methylbenzamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SANOFI-AVENTIS; US2009/281107; (2009); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 39549-79-6,Some common heterocyclic compound, 39549-79-6, name is 2-Amino-4-methylbenzamide, molecular formula is C8H10N2O, 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: A 12mL vial was charged with MCM-41-2P-Pd(OAc)2 (2molpercent), 2-aminobenzamide (1mmol), aryl iodide (1mmol) (if solid) and a stirring bar. Then, DMF (2mL), aryl iodide (1mmol) (if liquid) and DBU (2mmol) were injected by syringe under an argon atmosphere. The vial was placed in an alloy plate, which was transferred into a 300mL Parr Instruments 4560 series autoclave under an argon atmosphere. After flushing the autoclave three times with CO, a pressure of 10bar CO was fixed at ambient temperature. The autoclave was heated for 20hat 120°C. After completion of the reaction, the autoclave was cooled to room temperature and the pressure was released carefully. The reaction mixture was diluted with ethyl acetate (10mL) and filtered. The palladium catalyst was washed with distilled water (2×5mL) and acetone (2×5mL), and reused in the next run. The filtrate was concentrated in vacuo and the pure product was isolated by either washed with water, ethyl acetate and finally hexane or recrystallization from MeOH.

The synthetic route of 39549-79-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; You, Shengyong; Huang, Bin; Yan, Tao; Cai, Mingzhong; Journal of Organometallic Chemistry; vol. 875; (2018); p. 35 – 45;,
Amide – Wikipedia,
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Some common heterocyclic compound, 1103234-56-5, name is 2,6-Difluoro-3-(propylsulfonamido)benzoic acid, molecular formula is C10H11F2NO4S, 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. Product Details of 1103234-56-5

Example- 1 Preparation of 3-(Propane-l -sulfonylamino)-benzoyl chloride (IotaPi) Charge 2, 6-difiuoro-3-(((propan-l-yl) sulphonyl) amino) benzoic acid (5gm, 0.018 mol) was charged in to a reaction flask at 2S-30Ccontaining Toluene (25ml) under nitrogen atmosphere. Reaction mass was cooled to 10-15C. Thionyl chloride (15ml, 0.077mol) was added drop wise to mass at 10-15C and stirred for 15min. Reaction mass allowed to warm 25-30C and stirred for 30min. Heated the reaction mass to 105-110C and stirred for 4 hrs. Reaction mass cooled to 55-60C and organic volatiles distilled off completely to get semisolid residue and as such used in-situ for next stage.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1103234-56-5, its application will become more common.

Reference:
Patent; SHILPA MEDICARE LIMITED; PUROHIT, Prashant; NAGNNATH, Kokare; YENIREDDY, Veera Reddy; AKSHAY KANT, Chaturvedi; (0 pag.)WO2016/83956; (2016); 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. 71510-95-7, name is Ethyl 3-(methylamino)-3-oxopropanoate, This compound has unique chemical properties. The synthetic route is as follows., name: Ethyl 3-(methylamino)-3-oxopropanoate

General procedure: In a round bottom flask, unsaturated aldehyde 2 (0.25 mmol, 1 equiv), amidomalonate 1 (0.3 mmol, 1.2 equiv), catalyst (0.05 mmol, 20% mol), and KOAc (0.3 mmol, 1.2 equiv) were added sequentially in 1 mL of 2,2,2-trifluoroethanol. The reaction was stirred at room temperature overnight. Then the crude was purified by column chromatography to furnish piperidine adducts 3.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 71510-95-7.

Reference:
Article; ?ihalova, Sylva; Valero, Guillem; Schimer, Ji?i; Humpl, Marek; Dra?insky, Martin; Moyano, Albert; Rios, Ramon; Vesely, Jan; Tetrahedron; vol. 67; 46; (2011); p. 8942 – 8950;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 6329-26-6, These common heterocyclic compound, 6329-26-6, name is Ethyl (2-chloroethyl)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.

a) A mixture of 1-(4-bromophenyl)piperazine (0.018 mol) and ethyl (2-chloroethyl)-carbamate (0.036 mol) was stirred for 2 hours at 130 C. Triethylamine (3 ml) was added and the mixture was stirred for 15 minutes at 130 C. The reaction mixture was cooled to room temperature, CH2 Cl2 was added and the resulting mixture was washed with water. The organic layer was separated, dried, filtered and the solvent was evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2 Cl2 /CH3 OH 95/5). The pure fractions were collected and the solvent was evaporated, yielding 4.3 g (67.2%) of ethyl [2-[4-(4-bromophenyl)-1-piperazinyl]-ethyl]carbamate (interm. 1).

Statistics shows that Ethyl (2-chloroethyl)carbamate is playing an increasingly important role. we look forward to future research findings about 6329-26-6.

Reference:
Patent; Janssen Pharmaceutica, N.V.; US6103725; (2000); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 16066-84-5,Some common heterocyclic compound, 16066-84-5, name is tert-Butyl methylcarbamate, 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.

General procedure: JohnPhos (22 mg, 0.075 mmol), NaO’Bu (54 mg, 0.564 mmol), Pd2(dba)3(69 mg, 0.075 mmol), and then pyrrolidin-3-ol (49 mg, 0.564 mmol) were added to a solution of Compound 4 (200 mg, 0.376 mmol) and dioxane (5 mL). The mixture was degassed with vacuum/N2 cycles (3chi), stirred at 100 C overnight, filtered, and then concentrated. The residue was purified by RP-HPLC (H20 (100 mM H4HC03)/ACN) to give Compound 6 (58 mg, 29%) as a white solid. 1H NMR (400 MHz, DMSO-i): delta 8.13 (d, 1H), 7.39-7.75 (m, 6H), 7.31 (d, 2H), 7.07 (d, 1H), 6.95-6.99 (m, 1H), 6.72 (s, 1H), 5.08 (d, 1H), 5.02 (d, 1H), 4.79 (d, 1H), 4.43 (d, 1H), 3.80 (s, 3H), 3.47-3.55 (m, 1H), 3.43 (d, 2H), 3.21-3.25 (m, 1H), 2.18 (s, 3H), 1.95-2.10 (m, 1H), 1.90-2.10 (m, 1H), 1.73-1.85 (m, 2H), 0.80 (s, 9H); MS: 538.4 [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 tert-Butyl methylcarbamate, its application will become more common.

Reference:
Patent; METACRINE, INC.; SMITH, Nicholas D.; GOVEK, Steven P.; NAGASAWA, Johnny Y.; (167 pag.)WO2018/170167; (2018); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics