Month: February 2021

Reference of 5202-85-7, The chemical industry reduces the impact on the environment during synthesis 5202-85-7, name is 2-Amino-5-chlorobenzamide, I believe this compound will play a more active role in future production and life.

General procedure: A solution of anthranilamide (30 mmol) in 1 N HCl (120 mL) was stirred at 0 C for 20 min. Then, sodium nitrite (60 mmol) dissolved in deionized water (100 mL) was added dropwise to the above solution for 40 min. After another 2 h of stirring at 0 C, 30% NaOH solution was added slowly to adjust the pH to 8.0. The reaction mixture was allowed to stir vigorously for 15 min. The precipitated product was filtered off with suction, washed with deionized water (200 mL), and dried to afford compound 4 in yield of 82%.

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, 2-Amino-5-chlorobenzamide, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Chen, Xiulei; Jia, Haowu; Li, Zhong; Xu, Xiaoyong; Chinese Chemical Letters; vol. 30; 6; (2019); p. 1207 – 1213;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

These common heterocyclic compound, 630-22-8, name is 2,2-Dimethylpropanethioamide, 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. Formula: C5H11NS

General procedure: A mixture of 60 (5.4g, 35.0mmol), pyridine (11.4ml, 140mmol), and diethyl bromomalonate (3) (8.84ml, 52.5mmol) in EtOH (15ml) was heated under reflux for 16h. The mixture was concentrated under reduced pressure and H2O was added to the residue. The resulting precipitate was removed by filtration and washed with Et2O to deliver ethyl 2-(2-aminopyrimidin-4-yl)-4-hydroxythiazole-5-carboxylate (5.30g, 19.9mmol, 57% yield) as a tan solid.

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

Reference:
Article; Reichelt, Andreas; Bailis, Julie M.; Bartberger, Michael D.; Yao, Guomin; Shu, Hong; Kaller, Matthew R.; Allen, John G.; Weidner, Margaret F.; Keegan, Kathleen S.; Dao, Jennifer H.; European Journal of Medicinal Chemistry; vol. 80; (2014); p. 364 – 382;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 631-58-3, A common heterocyclic compound, 631-58-3, name is Propanethioamide, molecular formula is C3H7NS, 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.

To a stirring solution of 2-(2-chloropyrimidin-4-yl)-1-(3-methyl-5-{[(triisopropylsilyl)oxy]methyl}phenyl)ethanone (2.47 g, 1.0 eq) in DCM (85 ml.) was added NBS (1.07 g, 1.05 eq). After stirring 0.25 h, the reaction mixture was concentrated and taken up in DMF (40 ml.) and treated with thiopropionamide (0.75 g, 1.5 eq). After stirring 1 h, the reaction mixture was quenched with NaHCOs (aq) and extracted 2X with EtOAc. The organic extracts were dried over MgSO4, filtered, concentrated onto silica gel, and purified by column chromatography (gradient elution: 0 to 60% hexane/EtOAc) to provide 0.51 g (26%) of the title compound of Step C; 1H NMR (400 MHz, CDCI3) delta 8.36 (d, J = 5.5 Hz, 1 H), 7.41 (s, 1 H), 7.32 (s, 1 H), 7.28 (s, 1 H), 7.06 (d, J = 5.3 Hz, 1 H), 4.73 (s, 2 H), 3.20 (q, J = 7.5 Hz, 2 H), 2.37 (s, 3 H), and 1.50 (t, J = 7.6 Hz, 3 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; SMITHKLINE BEECHAM CORPORATION; WO2009/32667; (2009); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 112257-19-9, 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. 112257-19-9 name is tert-Butyl methyl(2-(methylamino)ethyl)carbamate, 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.

To a solution of MC-Val-Cit-PABC-PNP (93.0 mg, 0.126 mmol) in DMF (2 mL) was added N-Boc,N,N?-dimethylethylenediamine (23.7 mg, 0.126 mmol). Diisopropylethylamine (0.20 mL) was added, and the reaction stirred at room temperature for 3 h. The reaction mixture was acidified by adding acetic acid (0.50 mL), and purified by preparative HPLC (5percent to 95percent acetonitrile in water with 0.1percent TFA) to give 19? (53.2 mg, 0.0676 mmol, 53percent yield).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, tert-Butyl methyl(2-(methylamino)ethyl)carbamate, and friends who are interested can also refer to it.

Reference:
Patent; TARVEDA THERAPEUTICS, INC.; BILODEAU, Mark T.; SIMCOX, Mary; WHITE, Brian H.; KADIYALA, Sudhakar; WOOSTER, Richard; (178 pag.)WO2017/180834; (2017); 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. 90-16-4, name is Benzo[d][1,2,3]triazin-4(3H)-one, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C7H5N3O

A mixture of compound (20 g), obtained from step f of Example 1, triphenyl phosphine (17.6 g) and l,2,3-benzotriazin-4(3H)-one (7.2 g) were dried in high vacuum in a round bottom flask for 10 minutes. The vacuum was released under a nitrogen atmosphere and tetrahydrofuran (200 mL) was added to the above reaction mixture. The reaction mixture was cooled to O0C and diisopropyl azodicarboxylate (9.8 mL) was added slowly. The reaction mixture was stirred for 30 minutes at same temperature, and then quenched with water and extracted with ethyl acetate. The organic layer was washed with water, brine solution, dried over anhydrous sodium sulphate and concentrated to obtain a residue which was purified by column chromatography over silica gel using 30% ethylacetate in hexane as eluant to afford the title compound (22 g). Mass (m/z): 586.24 (M+ +1).

According to the analysis of related databases, 90-16-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; RANBAXY LABORATORIES LIMITED; WO2008/23336; (2008); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Some common heterocyclic compound, 123986-64-1, name is tert-Butyl 4-(hydroxymethyl)benzylcarbamate, molecular formula is C13H19NO3, 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: C13H19NO3

3) Synthesis of 1-[4-[N-(tert-butoxycarbonyl)aminomethyl]benzyl]-4-phenylpiperidine 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 then stopped by adding saturated aqueous solution of sodium hydrogen carbonate and the 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 6.72 g (21.07 mM) of crude product as light-brown solid. To a solution of 6.72 g (21.07 mM) of this crude mesylate in ethanol (42 ml) was added 5.9 ml (42.33 mM) of triethylamine as well as 3.40 g (21.09 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 magnesium sulfate. After concentration, the crude product was purified by column chromatography (ethyl acetate-hexane: 50%) to provide the title compound as light-yellow solid. Yield 5.77 g (72%) m.p. 73-74 C. 1H-NMR (200 MHz, CDCl3) delta: 1.46 (9H, s), 1.73-1.88 (4H, m), 1.99-2.19 (1H, m), 2.94-3.08 (2H, m), 3.54 (2H, s), 4.31 (2H, d, J=5.8 Hz), 4.73-4.96 (1H, m), 7.13-7.36 (4H, m). IR (KBr): 3389, 1690, 1518, 1269, 1171 cm-1.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 123986-64-1, its application will become more common.

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

Reference of 1129-26-6,Some common heterocyclic compound, 1129-26-6, name is 4-Methoxybenzenesulfonamide, molecular formula is C7H9NO3S, 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: To a stirred solution of the intermediates compound2a-2d (1 mmol) with triethylamine (2 mmol) into DMF(12 mL), then a mixture of 1-ethyl-(3-(3-dimethylamino)-propyl)-carbodiimide hydrochloride (EDCI) (1 mmol) andN-hydroxybenzotriazole (HOBt) (1 mmol) was placed in thereaction system, stirred at room temperature for 30 min, themixture of substituted benzene sulfonamide (1 mmol) andDMF (5 mL) was added in the reaction system, the reactionmixture was monitored by TLC. After completion of the reaction,the product was extracted from chloroform with water,0.2 mol/L hydrochloric acid, water, 2.0 mol/L sodium hydroxide,saturated sodium chloride successively, and then dried,concentrated, and purified by preparative thin layer chromatographyfollowed by recrystallization from ethanol.

The synthetic route of 1129-26-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Lv, Xian-Hai; Ren, Zi-Li; Liu, Hao; Li, Hai-Dong; Li, Qing-Shan; Wang, Li; Zhang, Li-Song; Yao, Xiao-Kang; Cao, Hai-Qun; Chemical and Pharmaceutical Bulletin; vol. 66; 4; (2018); p. 358 – 362;,
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. 915087-25-1, name is 4-Amino-2-fluoro-N-methylbenzamide, A new synthetic method of this compound is introduced below., category: amides-buliding-blocks

Example 3: Preparation of formula 4 TMSCN [74 g] was combined with N-methyl-2-fluro-4-aminobenzamide [formula 3, 50 g] in a clean and dried RBF. Acetic acid [250 ml] was slowly added dropwise to create frothing. Next, acetone [250 ml] was added and the reaction mass was heated to about 85 C. Heating continued until the reaction was complete. Next, the solvents were completely distilled off under vacuum (680 + 30 mm Hg). The resultant solid residue was cooled to room temperature, water [1000 ml] was added to the residue, and the reaction mass was stirred to get a free-flowing solid. The solid was filtered and washed with water to form a slurry. The slurry was then washed with tert-butyl methyl ether (TBME). The filtered cake was suck dried and the product dried under vacuum to result in formula 4.

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; MYLAN LABORATORIES LTD; WAGH, Ghanshyam; BODUPALLI, Murali; YEWALE, Sampat; DHANANJAY, Shinde; GADAKAR, Mahesh Kumar; GORE, Vinayak; DANDALA, Ramesh; (19 pag.)WO2016/38560; (2016); 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. 24036-52-0, name is 6-Bromo-2H-1,4-benzoxazin-3(4H)-one, A new synthetic method of this compound is introduced below., COA of Formula: C8H6BrNO2

A mixture of 6-bromo-2H-benzo[b][1,4]oxazin-3(4H)-one (197 mg, 0.864 mmol), (S)-3-phenylmorpholine (172.7 mg, 1.058 mmol), 2-(dicylclohexylphosphino)-2′-(N,N-dimethylamino)biphenyl (11.2 mg, 0.028 mmol), tris(dibenzylideneacetone)dipalladium (0) (8.9 mg, 0.01 mmol), tetrahydrofuran (3.3 mL) and lithium bis(trimethylsilyl)amide in tetrahydrofuran (1 M, 1.93 mL, 2 mmol) was stirred at 70 C. overnight. The mixture was cooled to room temperature and saturated aqueous ammonium chloride and ethyl acetate were added. The layers were separated and the aqueous layer was extracted with ethyl acetate (3*). The organic layers were combined, dried over magnesium sulfate, filtered, and concentrated. The residue was purified by silica gel column chromatography (gradient: 0-25% ethyl acetate in heptanes) to afford the title compound (105.6 mg, 39.4%). 1H NMR (400 MHz, CHLOROFORM-d) delta ppm 3.01(1H, ddd, J=12.2, 9.3, 4.3 Hz), 3.29 (1H, m), 3.54 (1H, dd, J=11.4, 8.9 Hz), 3.92 (3H, m), 4.15 (1H, m), 4.48 (2H, s), 5.28 (1H, s), 6.37 (1H, d, J=2.5 Hz), 6.56 (1H, m), 6.72 (1 H, d, J=8.8 Hz), 7.16 (3H, m), 7.26 (1H, m), 7.24 (2H, s), 7.97 (1H, s).

The synthetic route of 24036-52-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Pfizer Inc; US2011/281854; (2011); 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. 672-58-2, name is 3-(Trifluoromethyl)benzenesulfonamide, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C7H6F3NO2S

General procedure: To a stirred solution of glucal (1 equiv.) and N-nucleophile (1.1 equiv.) inanhydrous 1,2-dichloroethanne (2 mL/mmol) under an atmosphere of argon was added Zn(OTf)2 (10 mol%) at 40?C. The reaction mixture was stirred untilthe complete consumption of the starting material (glycal). The solvent wasfiltered and concentrated in vacuo, and the crude residue was redissolved indichloromethane and loaded on a silica gel column. The product was purified by silica gel column chromatography using hexane/EtOAc as the eluent to affordthe 2,3-unsaturated N-glycosides. All of the products were confirmed by1H NMR, 13C NMR, and MS/HRMS spectroscopy and compared with that of literature data; characterization data of new products are outlined in the experimentalsection

According to the analysis of related databases, 672-58-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Reddy, Thurpu Raghavender; Battina, Suresh Kumar; Kashyap, Sudhir; Journal of Carbohydrate Chemistry; vol. 34; 3; (2015); p. 133 – 144;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics