Month: January 2021

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. 3119-02-6, name is 4-Cyanobenzenesulphonamide, A new synthetic method of this compound is introduced below., SDS of cas: 3119-02-6

General procedure: Note that compounds 18a to 18e are similar to compounds 6a to 6g described in examples above. Consequently they were synthesized using similar procedures to Example 7, above. Their synthesis is also indicated in FIG. 4 as reaction ?b?. To a round-bottom flask equipped with a stir bar was added 17a-e(1.0 eq) (prepared using similar procedures as described in Examples 2-5), hydroxylamine hydrochloride (2.0 eq), NaHCO3 (4.0 eq), and methanol (5.0 mL/mmol). The reaction was refluxed and stirred in a pre-heated 75 C. oil-bath for 6 h. The reaction mixture was cooled to room temperature, and the precipitate was filtered off and washed with methanol. The filtrate was concentrated in vacuo without further purification. Example 58 Synthesis of 151 (E)-N?-hydroxy-4-sulfamoylbenzimidamide (18a) (0215) The synthesis follows the general procedure described in Example 57. Yield: 70%. MP: 217-219 C. 1H NMR (400 MHz, DMSO-d6) delta =7.88-7.78 (m, 4H, -ArH), 5.93 (s, 2H, -SO2NH2).

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; Washington University; Tu, Zhude; Rosenberg, Adam; Liu, Hui; Han, Junbin; US2019/2450; (2019); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 40545-33-3, 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 40545-33-3 as follows.

General procedure: Sodium hydrogen sulfite (4 mmol) was added to a solution of anthranilamide 1 (2 mmol) and benzaldehyde 2 (2 mmol) in N,N- dimethylacetamide (5 mL). The mixture was heated under continuous stirring at 150 o C for 2-3 h and poured into ice water. The precipitate was then filtered, washed with water followed byethanol, and dried to yield the 2-arylquinazolinones 3-31. 5.1.2. 6-Methyl-2-(naphthalen-1-yl)quinazolin-4(3H)-one (3)Yield 434 mg (76%). Light-yellow solid. Mp: 264e265 C. IR(cm1): 3421 (NH), 3041, 1677 (C]O). 1H NMR (500 MHz, DMSOd6)d (ppm): 12.5 (s, 1H); 8.15 (d, J 7.5 Hz, 1H), 8.10 (d, J 8.5 Hz,1H), 8.05e8.02 (m, 2H); 7.78 (d, J 7.5 Hz, 1H), 7.69e7.56 (m, 5H),2.50 (s, 3H). 13C NMR (125 MHz, DMSO-d6) d (ppm): 161.7, 152.7, 146.6, 136.4, 135.7, 133.0, 131.7, 130.2, 128.2, 127.5, 127.2, 126.9,126.2, 125.16, 125.13, 125.0, 120.9, 20.8. HRMS (ESI): m/z 287.1181 (M H) (calcd for C19H15N2O, 287.1184).

According to the analysis of related databases, 40545-33-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Khadka, Daulat Bikram; Tran, Giap Huu; Shin, Somin; Nguyen, Hang Thi Minh; Cao, Hue Thi; Zhao, Chao; Jin, Yifeng; Van, Hue Thi My; Chau, Minh Van; Kwon, Youngjoo; Le, Thanh Nguyen; Cho, Won-Jea; European Journal of Medicinal Chemistry; vol. 103; (2015); p. 69 – 79;,
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Reference of 5202-85-7, A common heterocyclic compound, 5202-85-7, name is 2-Amino-5-chlorobenzamide, molecular formula is C7H7ClN2O, 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: In a typical experiment, a solution of phenylacetic acid (0.3mmol, 40.8mg) in DMF (0.5mL) was added to a 10mL vial with the VNU-21 catalyst (5.5mg, 5mol%). The mixture was stirred at 120C for 4h under an oxygen atmosphere. After that, the catalyst was removed by filtration. A solution of 2-aminobenzamide (0.2mmol, 27.2mg) in DMSO (0.5mL) was then added to the reactor. The mixture was additionally stirred at 120C for 5h under oxygen. The GC yield of benzaldehyde and 2-phenylquinazolin-2(3H)-one were monitored by withdrawing samples from the reaction mixture, quenching with brine (1mL), extracting with ethyl acetate (3¡Á1mL), drying over anhydrous Na2SO4, and analyzing by GC regarding diphenyl ether as internal standard. After the completion of the second step, the reaction mixture was cooled to room temperature. Resulting solution was quenched with brine (5mL), extracted by ethyl acetate (3¡Á5mL), dried over anhydrous Na2SO4 prior to the removal of solvent under vacuum. The crude product was purified by silica gel column chromatography using hexane and ethyl acetate (1:1, v/v) as eluent. The structure of 2-phenylquinazolin-4(3H)-one was verified by GC-MS, 1H NMR and 13C NMR. For the leaching test, after the first 4h reaction time, the catalyst was removed by filtration. The solution phase was transferred to a new and clean reactor. New phenylacetic acid was added, and the resulting mixture was subsequently stirred for additional 4h at 120C under an oxygen atmosphere. The yield of benzaldehyde was monitored by GC.

The synthetic route of 5202-85-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; To, Tuong A.; Vo, Yen H.; Nguyen, Hue T.T.; Ha, Phuong T.M.; Doan, Son H.; Doan, Tan L.H.; Li, Shuang; Le, Ha V.; Tu, Thach N.; Phan, Nam T.S.; Journal of Catalysis; vol. 370; (2019); p. 11 – 20;,
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Related Products of 34813-49-5, 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. 34813-49-5, name is 2-Methylpropane-2-sulfonamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 86 4-(2-Methyl-propane-2-sulfonylaminocarbonyl)-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-5′-carboxylic acid (4-iodo-3-methyl-phenyl)-amide. A suspension of 5′-(4-iodo-3-methyl-phenylcarbamoyl)-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-carboxylic acid (50 mg, 0.11 mmol) in CH2Cl2 (5 mL) was treated with EDCI (60 mg, 0.31 mmol), t-butyl sulfonamide (18 mg, 0.13 mmol) and a catalytic amount of DMAP. After stirring at rt overnight the mixture was partitioned between CH2Cl2 and water. The CH2Cl2 layer was then collected and evaporated. The product was isolated after a purification with a silica gel column and 2-5% MeOH in CH2Cl2 and a precipitation out of warm CH2Cl2 with excess of hexanes (15 mg, Yield:24%). HRMS m/z calcd for C23H29N4O4SI [M+H]+: 585.1027; Found: 585.1032.

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

Reference:
Patent; Madrigal Pharmaceuticals, Inc.; BOLIN, David, R.; CHEUNG, Adrian, Wai-hing; HAMILTON, Matthew, Michael; MARCOPULOUS, Nicholas; McDERMOTT, Lee, Apostle; QIAN, Yimin; EP2350311; (2013); B1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 122734-32-1, name is tert-Butyl (2-(methylamino)ethyl)carbamate, 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 122734-32-1, Recommanded Product: tert-Butyl (2-(methylamino)ethyl)carbamate

To a solution of dichlorobenzyl-piperidin-4-one (Example 74, step (i), 4.8 g) and acetic acid (1 ml) in dichloromethane (100 ml) was added (2-methylamino-ethyl)-carbamic acid tert-butyl ester (3.26 g) and the mixture was stirred for 5 minutes before addition of sodium triacetoxyborohydride (7.9 g). The reaction mixture was stirred for 12 hours before addition of sodium bicarbonate solution. The mixture was stirred for 1/2 hour and then partitioned between water and dichloromethane. The organic layer was separated, dried (MgSO4) and solvent removed by evaporation. Purification by Biotage 40S eluding 10%MeOH/2% triethylamine/dichloromethane gave the title compound (1.7 g). MS: ESI 316/318 (+H-(CH3)4COCO) 1H NMR: (CDCl3): delta 1.44 (9H, s), 1.50-1.60 (4H, m), 1.65-1.72 (2H, m), 1.95 (2H, td), 2.23 (3H, s), 2.34 (1H, tt), 2.88 (2H, d), 3.14-3.20 (2H, m), 3.41 (2H, s), 4.95-5.01 (1H, m), 7.13-7.15 (1H, m), 7.37 (1H, d), 7.42 (1H, d).

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

Reference:
Patent; AstraZeneca, AB; US6903085; (2005); B1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 127346-48-9, name is tert-Butyl (3-aminopropyl)carbamate hydrochloride, 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 127346-48-9, name: tert-Butyl (3-aminopropyl)carbamate hydrochloride

Step 1A. Synthesis of tert-butyl 3-(((3-((tert-butoxy)carbonylamino)propyl)methylamino)methyl)-4-fluorobenzoate Crude tert-butyl-4-fluoro-3(alpha-bromomethyl)benzoate (4.6 g., 16 mmol), prepared as described in (WO 95/18619, PCT/US95/00248), was dissolved in 100 mL THF, along with 3-tert-butoxycarbonylamino-1-propylamine hydrochloride (2.9 g., 16.6 mmol) and diisopropylethylamine added (4.6 g., 36 mmol). The solution was stirred overnight, diluted with 1N NaOH, and extracted with three portions of ether. The combined organics were washed with water and sat. NaCl, dried over MgSO4, and concentrated under vacuum to 5.7 g. of a yellow oil. This was purified by flash chromatography (CH2Cl2/EtOAc) to afford the product as a clear oil (2.04 g., ~35%). 1H-NMR (600 MHz, DMSO-d6): 7.99 (dd, J=2, 5.1 Hz, 1H), 7.78 (ddd, J=2.3, 2.8, 3.0 Hz, 1H), 7.22 (dd, J=8.8, 0.7, 1H), 6.73 (b, 1H), 3.68 (s, 2H), 2.94 (m, 2H), 2.15 (b, 1H), 1.51 (s, 9H), 1.49 (m, 2H), 1.33 (s, 9H); MS (ES): 765.4 [2M+H]+, 383.3 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, tert-Butyl (3-aminopropyl)carbamate hydrochloride, and friends who are interested can also refer to it.

Reference:
Patent; Bristol-Myers Squibb Pharma Company; US6569402; (2003); B1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

57561-39-4, name is tert-Butyl (2-hydroxyethyl)(methyl)carbamate, 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. Quality Control of tert-Butyl (2-hydroxyethyl)(methyl)carbamate

Compound 20 (10 g, 57 mmol)Soluble in 250mL of dry dichloromethane,Nitrogen bubbling,Dess-Martin oxidant (DMP, 26.6 g) was added in portions at 0 C.Add the room temperature reaction,TLC (PE/EA = 1/1) monitors the progress of the reaction.Post-processing,Add 500 mL of saturated sodium bicarbonate solution,500mL saturated aqueous sodium thiosulfate solution andStir in 800 mL of dichloromethane for 30 min.Layered, the organic layer is saturated with sodium bicarbonate,Saturated with sodium chloride,Dry over anhydrous sodium sulfate, filter,Concentration under reduced pressure gave a white oil, 8.65 g.

The synthetic route of 57561-39-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sichuan Bai Li Pharmaceutical Co., Ltd.; Zhu Yi; Li Jie; Wan Weili; Zhuo Shi; Li Gangrui; (28 pag.)CN109106951; (2019); A;,
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Amide – an overview | ScienceDirect Topics

Synthetic Route of 147751-16-4, 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. 147751-16-4 name is tert-Butyl methylsulfonylcarbamate, 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 terf-butyl methylsulfonylcarbamate (900 mg, 4.62 mmol), K2CO3 (1 .3 g, 9.63 mmol) in DMF (60 mL) was added 2-(chloromethyl)-6-(1 -(phenylsulfonyl)-l H-indol- 3-yl)benzo[d]oxazole (Intermediate 79, 1 .49 g, 3.52 mmol). The mixture was stirred at 50 C for 9 hrs. The reaction mixture was filtered. The filtrate was diluted with water (60 mL) and extracted with EtOAc (60 mLx3). The combined organic layer was washed with water (60 mLx3), dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated and purified by silica gel chromatography (petroleum ether/ EtOAc =6/1 – 3/1 ) to afford 1 .25 g (61 %) of the title compound as a yellow solid. LC-MS for C28H27N3O7S2+H+ [M+H]+ : calcd. 582.1 ; found: 582.7. 1H NMR (400 MHz, DMSO-afe) delta [ppm]:8.22 (s, 1 H), 8.13 (d, J = 1 .1 Hz, 1 H), 8.11 (s, 1 H), 8.09 (d, J = 1 .3 Hz, 1 H), 8.05 (d, J = 8.3 Hz, 1 H), 7.89 (d, J = 7.9 Hz, 1 H), 7.85 (d, J = 8.3 Hz, 1 H), 7.76 (dd, J = 8.3, 1 .5 Hz, 1 H), 7.73 – 7.68 (m, 1 H), 7.61 (t, J = 7.7 Hz, 2H), 7.47 – 7.42 (m, 1 H), 7.39 – 7.34 (m, 1 H), 5.17 (s, 2H), 3.57 (s, 3H), 1 .43 (s, 9H).

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

Reference:
Patent; ITEOS THERAPEUTICS; CAUWENBERGHS, Sandra; CROSIGNANI, Stefano; DRIESSENS, Gregory; DEROOSE, Frederik; (271 pag.)WO2015/140717; (2015); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 141449-85-6, 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. 141449-85-6 name is tert-Butyl hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate, 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.

A 40-mL vial was charged with 4-chlorobenzaldehyde (1.13 g, 8.04 mmol, 1.00 equiv), 1,2-dichloroethane (20 mL), tert-butyl hexahydropyrrolo[3,4-c]pyrrole-2(lH)-carboxylate (1.69 g, 7.96 mmol, 0.99 equiv) and sodium triacetoxyborohydride (5.09 g, 24.0 mmol, 2.99 equiv). The resulting solution was stirred overnight at room temperature and quenched by water (10 mL). The mixture was extracted with DCM (3 x 30 mL) and the organic layers were combined, washed with water (3 x 10 mL), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was chromatographed on a silica gel column to provide 2.15 g (79% yield) of tert-butyl 5-(4-chlorobenzyl)hexahydropyrrolo[3,4-c]pyrrole-2(lH)- carboxylate as an off-white solid. LCMS (ESI, m/z): 337 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, tert-Butyl hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; ABIDE THERAPEUTICS, INC.; GRICE, Cheryl A.; JONES, Todd K.; DUNCAN, Katharine K.; WEBER, Olivia D.; CISAR, Justin S.; MERIT, Jeffrey E.; (184 pag.)WO2017/87858; (2017); A1;,
Amide – Wikipedia,
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Application of 198989-07-0, A common heterocyclic compound, 198989-07-0, name is tert-Butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate, molecular formula is C10H18N2O2, 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.

Step 2.4: To a solution of 1?-(5-(4-acetamidopyridin-2-yl)pyrimidin-2-yl)spiro[cyclopropane-1 ,3?-indoline]- 6?-carboxylic acid (0.25 g, 0.62 mmol, 1 eq) in DMF (5 mL), the TBTU (0.24 g, 0.747 mmol, 1.2 eq), NMM (0.126 g, 1.25 mmoL, 2 eq) and 2,5-diaza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester (0.123 g, 0.623 mmol, 1 eq) were added at RT. RM was then stirred at RT for 16 h. After completion of reaction,reaction mixture was quenched with ice water (40 mL) and a solid was precipitated out. The solid was filtered off and re-dissolved in EtOAc (50 mL). The EtOAc solution of the desired compound was washed with water (2 x 40 mL), brine (40 mL), dried over Na2SO4, filtered and evaporated under reduced pressure to get the crude product. The crude product was triturated with Et20-hexane (3 x) to afford tert-butyl 5-(1 (5-(4-acetamidopyridin-2-yl)pyrimidin-2-yl)spiro[cyclopropane-1 ,3-indolinj-6?-ylcarbonyl)-2,5-diazabicycle-[2.2.1]heptane-2-carboxylate (0.35 g, 96.9%) as white solid.

The synthetic route of 198989-07-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GRUeNENTHAL GMBH; NARDI, Antonio; JAKOB, Florian; KONETZKI, Ingo; CRAAN, Tobias; HESSLINGER, Christian; DOODEMAN, Robin; (0 pag.)WO2016/8593; (2016); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics