Amides-buliding-blocks

Application of 142733-64-0, These common heterocyclic compound, 142733-64-0, name is tert-Butyl (cis-3-(hydroxymethyl)cyclobutyl)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.

Under nitrogen protection,Compound 3-Boc aminocyclobutylmethanol (83f) (350.0 mg, 1.7 mmol)And triethylamine (528.0 mg, 5.2 mmol) was dissolved in 10 mL of dichloromethane.Under ice water bath, methylsulfonyl chloride (219.0 mg, 1.9 mmol) was added dropwise.Stir at room temperature for 3 h.Dichloromethane and 0.2 N of dilute hydrochloric acid were added and extracted.The organic layer was washed twice with brine, dried and dried.The compound 3-((tert-butoxycarbonyl)amino)cyclobutyl)methyl methanesulfonate (83 g) (330.0 mg, 1.2 mmol)The next reaction was directly administered, and the yield was 67.9%.

The synthetic route of 142733-64-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chengdu Haichuang Pharmaceutical Co., Ltd.; Du Wu; Wen Kun; Ai Chaowu; He Jinyun; Li Xinghai; Chen Yuanwei; (28 pag.)CN109988120; (2019); A;,
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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 749927-69-3 as follows. COA of Formula: C8H7BrFNO

A mixture of 4-bromo-2-fluoro-N-methylbenzamide (900 mg, 3.9 mmol), 5-(4,4,5,5- tetramethyl-l,3,2-dioxaborolan-2-yl)pyrimidin-2-amine (710 mg, 3.2 mmol), tetrakis(triphenylphosphine)palladium (100 mg, 0.1 mmol) and potassium carbonate (1.3 g, 9.7 mmol) in toluene (6.0 mL) and ethanol (3.0 mL) and water (3.0 mL) was heated at 110 0C for 2 hours. After cooling to RT, the reaction mixture was quenched with water and extracted with diethyl ether. The solid was filtered and washed with water and diethyl ether to afford the desired product (720 mg).

According to the analysis of related databases, 749927-69-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; INCYTE CORPORATION; ZHUO, Jincong; METCALF, Brian; WO2008/64157; (2008); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Related Products of 6331-71-1, A common heterocyclic compound, 6331-71-1, name is 4-Amino-N,N-dimethylbenzamide, molecular formula is C9H12N2O, 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.

The triflate E-7c (22.1 mg, 0.05720 mmol, 1.0 eq) was combined with 4-(amino)-N,N- dimethyl benzamide (11.27 mg, 0.06864 mmol, 1.2 eq), palladium(II)acetate (1.28 mg, 0.005720 mmol, 0.1 eq), Xantphos (6.62 mg, 0.01144 mmol, 0.2 eq) and potassium carbonate (180.9 mg, 1.1440 mmol, 20 eq). To this was added degassed 1,4-dioxane (3.0 mL). The vessel was then sealed, evacuated, and flushed with N2. The reaction was heated to 100 0C and stirred for 18 hours. The reaction was then cooled. The solvent was removed under reduced pressure. The residue was taken up in 4 mL of methanol and filtered through a 0.45 micron syringe filter. Purification by reverse phase preparatory HPLC provided Compound [103]. Data for Compound [103]: LCMS m/e 401; 1H NMR (400 MHz, Methanol-^) delta ppm 1.72 (s, 3 H), 1.76 (s, 3 H), 3.14 (s, 6 H), 5.10 – 5.19 (m, 1 H), 7.40 – 7.46 (m, 1 H), 7.46 – 7.53 (m, 2 H), 7.81 – 7.91 (m, 2 H), 8.34 – 8.44 (m, 1 H), 8.47 – 8.57 (m, 1 H), 9.11 – 9.18 (m, 2 H), 9.37 – 9.45 (m, 1 H).

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; MERCK SHARP & DOHME CORP.; BANYU PHARMACEUTICAL CO., LTD.; GOTO, Yasuhiro; SAGARA, Takeshi; FAN, Weiming; HAXELL, Thomas, F. N.; JENKS, Matthew, G.; MALASKA, Michael, J.; MOORE, Joseph, A., III; OUVRY, Gilles; PANDI, Bharathi; PEEL, Michael, R.; STEWARD, Kimberly, M.; WO2010/42337; (2010); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 3144-09-0, 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. 3144-09-0 name is Methylsulfonamide, 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.

8.4 g (0.02 mol) of 2-{4-[N-(5,6-diphenylpyrazin-2-yl)-N-isopropylamino] butyloxy} acetic acid and 60 mL of dichloromethane were added into a 100 mL flask and cooled to 5 C., 3.8 g (0.03 mol) of oxalyl chloride was added dropwise, then reacted at room temperature for 2 hours, the solvent was concentrated to dryness, 50 mL of acetonitrile was added to dissolve, and the X4 solution was obtained as a stand-by. (0077) 2.85 g of methanesulfonamide, 20 mL of acetonitrile and 3 g of triethylamine were added into another flask and cooled to 10 C., the X4 solution obtained above was added dropwise, then reacted at this temperature for 5 hours, until the reaction was completed. (0078) The finished reaction solution was poured into 100 mL of ice water, the mixture was extracted with ethyl acetate, the solvent of the organic phase was concentrated to dry, the residue was recrystallized with ethanol, and 8.8 g off-white crystals of NS-304 was obtained, the molar yield was 88%, HPLC purity was 99.5%. (0079) 1H-NMR data: 1H-NMR (400 MHz, CDCl3) delta: 8.19 (s, 1H), 7.44 (m, 2H), 7.35 (m, 2H), 7.30-7.21 (m, 6H), 3.97 (s, 2H), 3.59 (t, J=6.0 Hz, 2H), 3.45 (t, J=6.8 Hz, 2H), 3.29 (s, 3H), 1.75-1.70 (m, 4H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methylsulfonamide, and friends who are interested can also refer to it.

Reference:
Patent; Seasons Biotechnology (Taizhou) Co., Ltd.; TANG, Fanghui; MA, Chi; JIA, Qiang; (11 pag.)US2018/29998; (2018); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application 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.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Amino-4-methylbenzamide, its application will become more common.

Reference:
Article; You, Shengyong; Huang, Bin; Yan, Tao; Cai, Mingzhong; Journal of Organometallic Chemistry; vol. 875; (2018); p. 35 – 45;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 17641-08-6,Some common heterocyclic compound, 17641-08-6, name is 2-Chloro-N-(3-methoxyphenyl)acetamide, molecular formula is C9H10ClNO2, 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: The oxime 6 or 8 (0.7 mmol) and K2CO3(0.116 g, 0.84 mmol) were taken in dry DMF (5 mL), cooled to 0 Cand stirred for 30 min, then N-substituted acetamide (0.77 mmol)was added. The total reaction mixture was stirred at room temperature for 12-20 h. The reaction was monitored by TLC and after completion of the reaction, treated with ice cold water. Aqueous solution was extracted thrice with ethylacetate, combined extracts were washed with water till washings are neutral to pH, dried over anhydrous sodium sulfate and concentrated. The residue was purifiedby passing through a column packed with silica gel using petroleum ether/EtOAc (8:2) as eluent.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Chloro-N-(3-methoxyphenyl)acetamide, its application will become more common.

Reference:
Article; Gannarapu, Malla Reddy; Vasamsetti, Sathish Babu; Punna, Nagender; Royya, Naresh Kumar; Pamulaparthy, Shanthan Rao; Nanubolu, Jagadeesh Babu; Kotamraju, Srigiridhar; Banda, Narsaiah; European Journal of Medicinal Chemistry; vol. 75; (2014); p. 143 – 150;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 672-58-2,Some common heterocyclic compound, 672-58-2, name is 3-(Trifluoromethyl)benzenesulfonamide, molecular formula is C7H6F3NO2S, 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: In 25ml RB flask to a solution of Compound 9 (200 mg) in dry DMF (5ml), EDCI (250 mg, 1.25eq) and DMAP (130 mg,1eq) were added followed by addition of Sulfonamide (1eq). RM was stirred at RT for 4hrs. Solvent from the reaction mixture was evaporated. To the residue water was added and acidified with 6N HCl, solid precipitated out. Solid was filtered and dried. Crude solid was purified by flash chromatography eluating with 4-8% MeOH/DCM as solvent system to give pure product.

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

Reference:
Article; Patil, Vikas; Kale, Manoj; Raichurkar, Anandkumar; Bhaskar, Brahatheeswaran; Prahlad, Dwarakanath; Balganesh, Meenakshi; Nandan, Santosh; Shahul Hameed; Bioorganic and Medicinal Chemistry Letters; vol. 24; 9; (2014); p. 2222 – 2225;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

54616-47-6, name is 2-Bromo-N,N-dimethylbenzamide, 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. Formula: C9H10BrNO

General procedure: To a stirred solution of 1 (0.23 g, 1.0 mmol) in THF (6 mL) at -78C was added n-BuLi (1.6 M in hexane; 1.0 mmol) dropwise. After 15 min, PhNCS(0.14 g, 1.0 mmol) was added and stirring was continued for an additional 5 min before addition of saturated aqueous NH4Cl (15 mL). The mixture was extracted with AcOEt (3 × 10 mL), and the combined extracts were washed with brine (10 mL), dried (Na2SO4) and concentrated by evaporation

The synthetic route of 54616-47-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kobayashi, Kazuhiro; Shigemura, Yuuho; Fujiwara, Daiki; Heterocycles; vol. 94; 6; (2017); p. 1152 – 1158;,
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. 22961-58-6, name is 5-Amino-2-methoxybenzamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Quality Control of 5-Amino-2-methoxybenzamide

EXAMPLE 67 3′-Methoxy-2′-methylcarbamoyloxanilic acid ethyl ester. 72 Slow addition of 4.98 g. (0.03 mole) of 5-amino-o-anisamide to a mixture of 57% NaH (1.32 g., 0.0315 mole) in 50 ml. dimethylformamide was carried out at room temperature. After the evolution of H2 ceased, the mixture was cooled to 3 C. and 2.06 ml. (0.033 mole) of methyliodide was slowly added at 3-5 C. The temperature was allowed to go up to room temperature and stir for 2 hours. The mixture was concentrated, the residue extracted into ethylacetate-water, the mixture was basified, and the ethylacetate layer was washed with water, brine and dried. Concentration gave a tan solid that was crystallized (ethanol), giving 0.45 g. (8%) of 6-amino-N-methyl-o-anisamide mp. 186-189 C.

The synthetic route of 22961-58-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; American Home Products Corporation; US4054661; (1977); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 57957-24-1, name is N-(1-Phenylvinyl)acetamide, 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 57957-24-1, Safety of N-(1-Phenylvinyl)acetamide

General procedure: A reaction tube was charged with N-acetylenamide 1a (100 mg, 0.636 mmol), alkyne 2a (124 mg, 0.699 mmol), Cu(OAc)2.H2O (126 mg, 0.636 mmol), KPF6 (23.4 mg, 0.127 mmol) and [RuCl2(p-cymene)]2 (7.8 mg, 0.0127 mmol). To that, DME or water (3 mL) was added by syringe. The reaction mixture was stirred at 110 C under N2 as indicated time in the table 1.The reaction mixture was cooled down to rt, diluted with 10 mL of DCM. The mixture was then filtered through Celite. The combined organic portion was washed with water, then dried over MgSO4 and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel with hexane/ethyl acetate as eluent to yielded the desired pyrrole 3a (202 mg, 0.605 mmol) in 95% yield. Products obtained in this work were characterized by spectral methods particularly with 1H, 13C NMR, and ESI-Mass analyses, further, the data were compared with those reported.

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-(1-Phenylvinyl)acetamide, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Murugan, Kaliyappan; Liu, Shiuh-Tzung; Tetrahedron Letters; vol. 54; 21; (2013); p. 2608 – 2611;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics