Category: amides-buliding-blocks

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;,
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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

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

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;,
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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

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,
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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

Related Products of 72179-84-1, These common heterocyclic compound, 72179-84-1, name is (Methylsulfamoyl)amine, 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: N-Alkylsulfamide 7 (3.63mmol, 1equiv) was added to a stirred solution of arylaldehyde (4.00mmol, 1.1equiv) and Ti(OEt)4 (1.95g, 7.26mmol, 2equiv) in THF (10mL). The solution was stirred at reflux for 7h, allowed to cool and then poured into stirred brine (100mL), EtOAc (50mL) was added and the mixture was stirred vigorously. The mixture was then filtered through Celite and flushed with further EtOAc. The filtrate was separated and the aqueous layer was back extracted with EtOAc (50mL). The combined organic layers were washed with brine (50mL), dried (Na2SO4) and concentrated to a cream solid. Purification by column chromatography or trituration gave the products as colourless to cream solids (yellow for 9f).

Statistics shows that (Methylsulfamoyl)amine is playing an increasingly important role. we look forward to future research findings about 72179-84-1.

Reference:
Article; Crampton, Rosemary H.; Fox, Martin; Woodward, Simon; Tetrahedron Asymmetry; vol. 24; 9-10; (2013); p. 599 – 605;,
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 956434-30-3 as follows. Application In Synthesis of tert-Butyl 8-chloro-2,3-dihydropyrido[3,2-f][1,4]oxazepine-4(5H)-carboxylate

(Step 1) To a solution of the compound (0.500 g) obtained in Example 29, step 1 and iron(III) acetylacetonate (0.0620 g) in a mixture of THF (10 mL) and 1-methylpyrrolidinone (1 mL) was added 1M isopropylmagnesium chloride ether solution (8.78 mL), and the mixture was stirred at room temperature for 2 hr. The reaction mixture was poured into 1N hydrochloric acid, and the resultant product was extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate, and concentrated. The obtained residue was purified by silica gel column chromatography (solvent gradient; 5?100% ethyl acetate/hexane) to give tert-butyl 8-isopropyl-2,3-dihydropyrido[3,2-f][1,4]oxazepine-4(5H)-carboxylate (0.136 g, 27%) as an oil. 1H-NMR(CDCl3): delta 1.27(6H,d,J=7.0Hz), 1.42(9H,s), 2.93-3.02(1H,m), 3.82-3.84(2H,m), 4.22(2H,brs), 4.35-4.50(2H,m), 6.88(1H,d,J=7.5Hz), 7.40-7.60(1H,m) MS(ESI+):293(M+H)

According to the analysis of related databases, 956434-30-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP2018863; (2009); 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. 1746-77-6, name is Isopropyl carbamate, A new synthetic method of this compound is introduced below., SDS of cas: 1746-77-6

Intermediate 4 1-Methylethyl(2E)-2-butenoylcarbamate Isopropyl carbamate (30 g, 291 mmol, available from TCI) was charged to a 3 L Lara vessel and dry THF (150 ml) added. (2E)-2-Butenoyl chloride (31.2 ml, 326 mmol, available from Aldrich) was added under nitrogen and the jacket cooled to -30 C. When the solution temperature reached -17 C. lithium tert-butoxide (1M, 655 ml, 655 mmol) was added by peristaltic pump over 2 h, keeping the reaction temperature between -10 C. and -18 C. Once the addition was complete the mixture was stirred for 30 min and brought to 0 C. Diethyl ether (450 ml) and hydrochloric acid (1M, 375 ml) were added and the mixture brought to 20 C. with vigorous stirring. The stirring was stopped, the layers allowed to separate and the aqueous layer run off. Brine (375 ml) was added and the mixture stirred vigourously. The stirring was stopped, the layers allowed to separate and the aqueous layer run off. The organic layer was dried (MgSO4), filtered and evaporated to a brown oil (60 g). The oil was applied to a silica column (40+M Biotage) and eluted with DCM/ethyl acetate (1:1 to 0:1, 10 CV). The product containing fractions were evaporated to dryness and loaded on to a silica column (1500 g, Redisep Isco) and eluted with a ethyl acetate in cyclohexane gradient (0-40%). The clean, product containing fractions were evaporated to an off-white solid (15.41 g). LCMS (Method C), Rt 0.68, MH+172

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; GlaxoSmithkline LLC; Amans, Dominique; Demont, Emmanuel Hubert; Jones, Katherine Louise; Seal, Jonathan Thomas; Walker, Ann Louise; US2014/66459; (2014); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics