Author: Jessica.F

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. 97308-23-1, name is tert-Butyl aziridine-1-carboxylate, A new synthetic method of this compound is introduced below., Product Details of 97308-23-1

Step 4 To the solution tert-butyl aziridine-1-carboxylate LXXXVI (excess) in dioxane was added (2-aminioethyl)trimethylazanium dichloride LXXXIV (0.25 g; 1.8 mmol). The mixture was refluxed for 3 days. The solvent was removed under reduced pressure and the residue was purified on a silica gel column (100:1 CHCl3:MeOH) to give crude tert-butyl N-(2-{[2-(trimethylaminio)ethyl]amino}ethyl)carbamate chloride LXXXVII was used directly for step 5.

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; Mpex Pharmaceuticals, Inc.; US2008/318957; (2008); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Some common heterocyclic compound, 138-41-0, name is Carzenide, molecular formula is C7H7NO4S, 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. name: Carzenide

A. 4-Sulfamoyl-benzoic acid methyl ester. To a stirred suspension of 4-sulfamoyl-benzoic acid (25.0 g, 0.124 mol) in 4:1 CH2Cl2/MeOH at rt was added 1.0 M TMSCHN2 in hexane (175 mL), and the reaction mixture was allowed to stir for 2 h. The mixture was diluted with 1 N NaOH (100 mL) and CH2Cl2 (150 mL), and the layers were separated. The organic layer was dried over Na2SO4, then filtered, and the solvent was removed under reduced pressure to afford the desired ester (25.2 g, 95%), which was used without further purification. 1H NMR (400 MHz, DMSO-d6): 8.14 (d, J=8.1 Hz, 2H), 7.96 (d, J=8.1 Hz, 2H), 7.58 (s, 2H), 3.90 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 138-41-0, its application will become more common.

Reference:
Patent; Deng, Xiaohu; Mani, Neelakandha; Mapes, Christopher M.; US2006/4195; (2006); A1;,
Amide – Wikipedia,
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Reference of 107017-73-2, These common heterocyclic compound, 107017-73-2, name is tert-Butyl (1-(hydroxymethyl)cyclopropyl)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.

4-(3-(4-Hydroxyphenyl)-4,4-dimethyl-5-oxo-2-thioxoimidazolidin-1-yl)-2-(trifluor omethyl)benzonitrile 14c (100 mg, 0.25 mmol) was placed in a reaction flask, followed by addition of tert-butyl (1-(hydroxymethyl)cyclopropyl)carbamate 6a (93 mg, 0.49 mmol), triphenylphosphine (97 mg, 0.37 mmol), 5 mL of dichloromethane and diisopropyl azodicarboxylate (75 mg, 0.37 mmol) successively. The reaction solution was stirred for 2 hours. The reaction solution was concentrated under the reduced pressure and the residue was purified by thin layer chromatography with elution system A to obtain the title compound tert-butyl (1-((4-(3-(4-cyano-3-(trifluoromethyl)phenyl)-5,5-dimethyl-4-oxo-2-thioxoimidazolidin -1-yl)phenoxy)methyl)cyclopropyl)carbamate 37a (50 mg, yield 35.2%) as a white solid. MS m/z (ESI): 519.3 [M-56+1]

Statistics shows that tert-Butyl (1-(hydroxymethyl)cyclopropyl)carbamate is playing an increasingly important role. we look forward to future research findings about 107017-73-2.

Reference:
Patent; Shanghai Hengrui Pharmaceutical Co. Ltd.; Jiangsu Hengrui Medicine Co. Ltd.; LU, Hejun; SUN, Piaoyang; FEI, Hongbo; JIANG, Hongjian; WANG, Haowei; DONG, Qing; EP2894151; (2015); 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 406233-31-6 as follows. name: 4-Fluoro-3-nitrobenzenesulfonamide

General procedure: To an ice cold stirred solution of compound 4a-4u (1 eq) in anhydrousDCM (10 mL for 1 mmol of substrate), TEA (3 eq) was added dropwise and stirred for 10 min. Compound 5 (1 eq) was added slowly andstirred at RT for 16 h (precipitation was observed during the reactionprogress). TLC showed completion of reaction. The reaction mixturewas concentrated under reduced pressure. Water was added to thecrude material and stirred for 30 min. Obtained solid was filtered,washed with water and dried under vacuum. The solid was trituratedwith ethyl acetate, filtered and dried under high vacuum to affordcompound 6a-v.

According to the analysis of related databases, 406233-31-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Kalisha Vali; Gundla, Rambabu; Singh, Om V.; Tamboli, Yasinalli; Di Cesare Manelli, Lorenzo; Ghelardini, Carla; Al-Tamimi, Abdul-Malek S.; Carta, Fabrizio; Angeli, Andrea; Supuran, Claudiu T.; Bioorganic Chemistry; vol. 92; (2019);,
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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

Triethylamine (4.68 mL, 33.59 mmol) and diphenylphosphonic azide (3.73 mL, 16.79 mmol) were added to a solution of 2,6-difluoro-3-(propylsulfonamido)benzoic acid (4.078 g, 14.6 mmol) in THF (60 mL). The reaction mixture was stirred at room temperature for 3 hours and then warmed to 80C for 2 hours. Water (10 mL) was added, and the mixture was stirred at 80C for 15 hours. The reaction mixture was diluted with EtOAc (300 mL), and the organic layer was washed with saturated aqueous NaHC03 solution and brine. The solvent was removed under reduced pressure, and the residual purified via silica gel column chromatography eluting with 30/70 EtOAc/hexane to obtain 2.03 g (55%) of the title compound. 1H NMR (400 MHz, DMSO-d6) delta 9.32 (s, 1H), 6.90-^.80 (m, 1H), 6.51 (td, J=8.7, 5.5, 1H), 5.28 (s, 2H), 3.05-2.96 (m, 2H), 1.82-1.64 (m, 2H), 1.01-0.90 (m, 3H). LC/MS: w/z 251.1 [M+l].

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; ARRAY BIOPHARMA INC.; GENENTECH, INC.; GRINA, Jonas; HANSEN, Joshua D.; LAIRD, Ellen; MATHIEU, Simon; MORENO, David; REN, Li; RUDOLPH, Joachim; WENGLOWSKY, Steven Mark; WO2012/118492; (2012); A1;,
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Reference of 579474-47-8, These common heterocyclic compound, 579474-47-8, name is tert-Butyl 2-amino-4-fluorophenylcarbamate, 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 solution of 0110-31 (200 mg, 0.4 mmol), TBTU (200 mg, 0.6 mmol), N1, Lambdaf2-diisopropylethane-l, 2-diamine (364 mg, 2.82 mmol), and tert-butyl 2-amino-4- fluorophenylcarbamate (0113-60) (90 mg, 0.4 mmol) in DMF (4 mL) and THF (2 mL) was stirred at r.t. for 3 hours. Then DMF and THF were removed under reduced pressure and the residue was dispensed in water and filtered to get the crude product. The crude compound was further purified by flash column chromatography on silica gel (ethyl acetate in petroleum ether, 50% v/v) to afford pure product tert-butyl 2-(4- (4-(2-(5-((5-tert-butyloxazol-2-yl)methylthio)thiazol-2-ylamino)-2- oxoethyl)phenoxy)butanamido)-4-fluorophenylcarbamate (150 mg, 54%) as a pale yellow solid. LCMS : 698 [M+ 1 ]+.

Statistics shows that tert-Butyl 2-amino-4-fluorophenylcarbamate is playing an increasingly important role. we look forward to future research findings about 579474-47-8.

Reference:
Patent; CURIS, INC.; QIAN, Changgeng; CAI, Xiong; ZHAI, Haixiao; WO2010/75542; (2010); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 167216-30-0, The chemical industry reduces the impact on the environment during synthesis 167216-30-0, name is tert-Butyl (3-hydroxybutyl)carbamate, I believe this compound will play a more active role in future production and life.

Step 2: Synthesis of tert-butyl 6-methyl-1,2,3-oxathiazinane-3-carboxylate 2-oxideTo a stirred solution of thionyl chloride (2.0 mL, 27.9 mmol) in acetonitrile (15 mL) cooled to -45 C is added a solution of tert-butyl (3-hydroxybutyl)carbamate (2.1 g, 11.2 mmol) in acetonitrile (20 mL) by syringe over 10 min, keeping the internal temperature below -40 C. 4-Dimethylaminopyridine (136 mg, 1.1 mmol) is added followed by the dropwise addition of pyridine (4.5 mL, 55.8 mmol, keeping the temperature below -40 C. The addition takes 90 min. Ethyl acetate (50mL) is added to the suspension and the mixture is filtered at -35 C to remove the solid and the solid which is washed with EtOAc before it is discarded. The filtrates are combined, and saturated Na2HP04 solution (20 mL) is added. The mixture is stirred vigorously for 30 min and the organic layer is separated, washed with 1M NaHS04 to remove residual pyridine, dried (MgS04) and concentrated to afford the title compound (2.52 g, 96%) as an oil.

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-hydroxybutyl)carbamate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BOYER, Stephen, James; GAO, Donghong, Amy; GUO, Xin; KIRRANE, Thomas, Martin, Jr.; SARKO, Christopher, Ronald; SNOW, Roger, John; SOLEYMANZADEH, Fariba; ZHANG, Yunlong; WO2011/71716; (2011); 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. 894852-01-8, name is 7-Bromo-2,2-dimethyl-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one, A new synthetic method of this compound is introduced below., name: 7-Bromo-2,2-dimethyl-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one

b) (E)-3 -(2,2-Dimethyl-3 -oxo-3 ,4-dihydro-2H-pyrido[3,2-&] [ 1 ,4]oxazin-7-yl)-iV-methyl-N- (3-methylbenzofuran-2-yhnethyl)acrylamide; A solution of N-methyl-N-(3-methylbenzofuran-2-yhnethyl)acrylamide (0.231 g,1.01 mmol) in propionitrile (4 mL) and DMF (0.8 mL) was deoxygenated with Ar for 20 min. The solution was treated with diisopropylethylamine (0.28 mL, 1.64 mmol) and 7- bromo-2,2-dimethyl-4H-rhoyrido[3,2-][l,4]oxazin-3-one (0.200 g, 0.775 mmol). The solution was deoxygenated with Ar for 20 min. Pd(OAc)2 (0.017 g, 0.078 mmol) and P(o- tol)3 (0.047 g, 0.15 mmol) were then added and the solution was deoxygenated again with Ar for 10 min. The mixture was heated to reflux for 18 h, then allowed to cool. The mixture was diluted with H2O (100 mL). The resulting solids were collected by filtration and washed with Et2O (50 mL). Residual palladium was removed by silica gel plug (silica gel, 95:5, CH2Cl2/Me0H) the resulting solution concentrated to reveal a light orange solid. The solid was triturated with Et2O and dried to give the title compound (0.14 g, 46%) as a light pink solid and as a mixture of amide rotamers: 1H NMR (300 MHz, DMSO-JPatent; AFFINIUM PHARMACEUTICALS, INC.; WO2007/53131; (2007); A2;,
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Amide – an overview | ScienceDirect Topics

Reference of 198989-07-0, The chemical industry reduces the impact on the environment during synthesis 198989-07-0, name is tert-Butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate, I believe this compound will play a more active role in future production and life.

a) iert-Butyl 5-(3-bromoimidazo[1 ,2-b]pyridazin-6-yI)-2,5diazabicyclo[2.2.1]heptane-2- carboxylate3-Bromo-6-chloroimidazo[1 ,2-b]pyridazine (586 mg, 2.53 mmol) was dissolved in NMP (5 mL) and 2,5-diazabicyclo[2.2.1]heptane-2-carboxylic acid 1 ,1-dimethylethyl ester (1.0 g, 5.05 mmol) was added followed by DIPEA (1.04 mL, 6.31 mmol). The reaction mixture was heated to 30C for 4 h. The solution was cooled down and diluted with DCM, then washed twice with water and twice with brine. The solution was dried over magnesium sulphate and solvents evaporated. Purification by column chromatography on silica gel (10- 00% EtOAc/petroleum ether) gave a brown oil. This was dissolved in ethyl acetate, washed four more times with brine, dried over magnesium sulphate and the solvents evaporated to give a brown solid (486 mg, 49%); H NMR (400 MHz, CDCI3) delta ppm 7.67 (d, J=9.6 Hz, 1 H), 7.67 (d, J=9.6 Hz, 1 H), 7.52 (s, 1 H), 6.54 (d, J=9.6 Hz, 1 H), 4.49-4.84 (m, 2H), 3.43-3.67 (m, 4H), 1.94-2.07 (m, 2H), 1.48 (s, 9H); m/z (ES+APCIf: 394/396 [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, tert-Butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MEDICAL RESEARCH COUNCIL TECHNOLOGY; OSBORNE, Simon; CHAPMAN, Timothy; WALLACE, Claire; WO2012/127212; (2012); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 2227-79-4,Some common heterocyclic compound, 2227-79-4, name is Benzothioamide, molecular formula is C7H7NS, 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 solution of ethyl bromopyruvate (0.68g, 3.5 mmol) and thiobenzamide(0.40 g, 2.9 mmol) in ethanol (25 mL) was heated to reflux for 4 h. The solvent was removed under reduced pressure, and the residue was washed with water (30ml) and extracted with ethyl acetate (3 ¡Á 20 mL). The organic layer was driedover anhydrous Na2SO4 and concentrated. The residue waspurified by silica gel column chromatography using a mixture of petroleum ether/ethyl acetate (20:1, v/v) as eluent to afford the desired product (0.52g, 76%) as a white solid.1H NMR (300 MHz, DMSO-d6) delta:8.96 (s, 1H, ArH), 7.89 (d, J=8.01Hz, 2H, ArH), 7.31 (m, 3H, ArH), 4.39 (q, J=7.12 Hz, 2H, -OCH2), 1.34 (t, J=7.12 Hz, 3H,-CH3).

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

Reference:
Article; Li, Zheng; Qiu, Qianqian; Xu, Xue; Wang, Xuekun; Jiao, Lei; Su, Xin; Pan, Miaobo; Huang, Wenlong; Qian, Hai; European Journal of Medicinal Chemistry; vol. 113; (2016); p. 246 – 257;,
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