Tag: M.W=200-300

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 864448-41-9 as follows. Formula: C11H20N2O3

To a mixture of 3-oxa-7,9-diaza-bicyclo[3.3.1]nonane-7-carboxylic acid tert-butyl ester (171 mg, 0.75mmol) and DIPEA(0.45 mL, 2.5 mmol) in CH2C12 (10 mL) was added (R)-6- bromomethyl-4-(2-chloro-4-fluoro-phenyl)-2-thiazol-2-yl-l,4-dihydro-pyrimidine-5-carboxylic acid methyl ester(222 mg, 0.5 mmol). The mixture was stirred at room temperature for 16 hours The mixture was concentrated in vacuo. The residue was purified by flash column chromatography to afford 9-[(R)-6-(2-chloro-4-fluoro-phenyl)-5-methoxycarbonyl-2-thiazol-2- yl-3,6-dihydro-pyrimidin-4-ylmethyl]-3-oxa-7,9-diaza-bicyclo[3.3.1]nonane-7-carboxylic acid tert-butyl ester as yellow oil (0.28 g, 94%). MS: calc’d (MH+) 592, measured (MH+) 592.

According to the analysis of related databases, 864448-41-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; GUO, Lei; HU, Taishan; HU, Yimin; KOCER, Buelent; KOU, Buyu; LI, Gangqin; LIN, Xianfeng; LIU, Haixia; SHEN, Hong; SHI, Houguang; WU, Guolong; ZHANG, Zhisen; ZHOU, Mingwei; ZHU, Wei; WO2014/184328; (2014); A1;,
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Adding a certain compound to certain chemical reactions, such as: 21440-97-1, name is 6-Bromo-4,4-dimethyl-1,4-dihydrobenzo[d][1,3]oxazin-2-one, 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 21440-97-1, Formula: C10H10BrNO2

6-bromo-4,4-dimethyl-lH-3,l-benzoxazin-2-one (250 mg, 0.976 mmol) was dissolved in dimethylformamide (5 mL) and potassium carbonate (0.204 g, 1.46 mmol) was added. The suspension was stirred for 10 min and then iodoethane (0.158 mL, 1.95 mmol) was added. The reaction mixture was heated to 60C and stirred for 4 h. The reaction mixture was poured into ice/water and then extracted with ethyl acetate (3×20 mL). The combined organic layers were washed with brine (2×20 mL). dried and concentrated. The crude oil was purified by flash chromatography to give the desired compound (0.275 g, 99%) as a colorless oil. LCMS: 0.98 min; ES+ 284/286 (M+H+); XH NMR (CHLOROFORM-d, 400MHz): delta (ppm) 7.43 (d,lH), 7.28 (s, 1H), 6.86 (d, 1H), 3.98 (q, 2H), 1.67 (s, 6H), 1.32 (t, 3H)

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, 6-Bromo-4,4-dimethyl-1,4-dihydrobenzo[d][1,3]oxazin-2-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; SYNGENTA PARTICIPATIONS AG; CUTLER, Sean, R.; LACHIA, Mathilde, Denise; WENDEBORN, Sebastian, Volker; GODFREY, Christopher, Richard Ayles; SABBADIN, Davide; (82 pag.)WO2018/17490; (2018); A1;,
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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. 141449-85-6, name is tert-Butyl hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate, A new synthetic method of this compound is introduced below., SDS of cas: 141449-85-6

A 50-mL round-bottom flask was charged with 2-fluoro-4-(trifluoromethyl)benzaldehyde (0.500 g, 2.60 mmol, 1.00 equiv) in dimethyl sulfoxide (10 mL), tert-butyl octahydropyrrolo[3,4-c]pyrrole-2-carboxylate (0.828 g, 3.90 mmol, 1.50 equiv), and potassium carbonate (1.08 g, 7.81 mmol, 3.00 equiv). The resulting solution was stirred overnight at 90 C. and quenched with water (20 mL). The mixture was extracted with ethyl acetate (3*20 mL) and the organic layers were combined, washed with brine (2*20 mL), dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was chromatographed on a silica gel column with ethyl acetate/petroleum ether (1/3) to provide 0.580 g (58% yield) of tert-butyl 5-(2-formyl-5-(trifluoromethyl)phenyl)hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate as a yellow solid. LCMS (ESI, m/z): 385 [M+H]+.

The synthetic route of 141449-85-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ABIDE THERAPEUTICS, INC.; GRICE, Cheryl A.; BUZARD, Daniel J.; SHAGHAFI, Michael B.; WEBER, Olivia D.; (127 pag.)US2019/202801; (2019); A1;,
Amide – Wikipedia,
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Electric Literature of 129686-16-4, These common heterocyclic compound, 129686-16-4, name is 6-Bromo-3,4-dihydro-1H-[1,8]naphthyridin-2-one, 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. Synthesis of the intermediates Example A.1 a) Preparation of intermediate (1) A solution of 6-bromo-3,4-dihydro-lH-[l,8]naphthyridin-2-one (1.0 g, 4.4 mmol), tert- butyl acrylate (2.56 ml, 17.62 mmol) and N,N-diisopropylethylamine (1.46 ml, 8.81 mmol) in acetonitrile (20 ml) and DMF (7 ml) was stirred and degassed with nitrogen gas for 10 minutes. Tri-o-tolylphosphine (0.27 g, 0.88 mmol) and palladium (II) acetate (47% on Pd) (0.099 g, 0.44 mol) were added and the resulting mixture was microwaved (1600 W, 180C, 35 minutes). The reaction mixture was evaporated till dryness, taken up in a mixture of DCM/methanol (8/2) (50 ml), filtered through a short pad of celite and washed with DCM. The organic layer was washed with water, dried (MgS04), filtered and evaporated to dryness. The residue was taken up in cold ethanol (10 ml) and stirred at 5C for 5 minutes, the precipitate was filtered off, washed with cold ethanol (3 ml) and dried under vacuum to yield 950 mg intermediate (1).

The synthetic route of 129686-16-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN R&D IRELAND; GUILLEMONT, Jerome, Emile, Georges; LANCOIS, David, Francis, Alain; MOTTE, Magali, Madeleine, Simone; KOUL, Anil; BALEMANS, Wendy, Mia, Albert; ARNOULT, Eric, Pierre, Alexandre; WO2013/21054; (2013); 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. 35303-76-5, name is 4-(2-Aminoethyl)benzenesulfonamide, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C8H12N2O2S

General procedure: To a cooled solution of triphosgene (1.41mmol) in THF at 0¡ãC, a mixture of primary amine (3.52mmol) and N,N-diisopropylethylamine (DIPEA, 7.04mmol) was added. The reaction mixture was stirred at the same temperature for 30min and then the other amine (3.52mmol) was added. The reaction mixture was slowly allowed to attain ambient temperature and further stirred for 8h. After the completion of the reaction, water was added to the reaction mixture and extracted using ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and evaporated under reduced pressure. The crude mixture was subjected to column chromatography to obtain the pure compounds.

According to the analysis of related databases, 35303-76-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Manickam, Manoj; Jalani, Hitesh B.; Pillaiyar, Thanigaimalai; Boggu, Pulla Reddy; Sharma, Niti; Venkateswararao, Eeda; Lee, You-Jung; Jeon, Eun-Seok; Son, Min-Jeong; Woo, Sun-Hee; Jung, Sang-Hun; European Journal of Medicinal Chemistry; vol. 143; (2018); p. 1869 – 1887;,
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Amide – an overview | ScienceDirect Topics

Electric Literature of 858671-91-7, These common heterocyclic compound, 858671-91-7, name is tert-Butyl 2,5-Diazabicyclo[2.2.2]octane-2-carboxylate, 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.

Anhydrous dimethylacetamide (655 mL, degassed prior to use) was added to a mixture of 5 -chloro-3 -methyl- 1 -(4,4,4-trifluoro-2,2-dimethylbutyl)- 1 ,3-dihydro-2H-imidazo[4,5- ¡ê]pyridin-2-one (34-2, 175 mg, 0.544 mmol), potassium phosphate tribasic (231 mg, 1.09 mmol), bis(tri-t-butylphosphine)palladium(0) (11.2 mg, 0.02 mmol), and tert-butyl-2,5- diazabicyclo[2.2.2]octane-2-carboxylate (115 g, 0.54 mmol). The resulting suspension was heated to 100 C for 18 h. Following this duration, the reaction contents were cooled to room temperature, filtered, and washed with acetonitrile. Purification using normal-phasechromatography (40% EtOAc in hexane) afforded tert-butyl 5-[3-methyl-2-oxo-l -(4,4,4- trifluoro-2,2-dimethylbutyl)-2,3-dihydro-lH-imidazo[4,5-?]pyridin-5-yl]-2,5- diazabicyclo[2.2.2]octane-2-carboxylate (34-3) as a white solid. MS m/z (Mu+Eta): calculated = 497.5; observed = 498.5.

The synthetic route of 858671-91-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; LAYTON, Mark, E.; PERO, Joseph, E.; RODZINAK, Kevin, J.; ROSSI, Michael, A.; WO2011/34741; (2011); A1;,
Amide – Wikipedia,
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These common heterocyclic compound, 2736-23-4, name is 2,4-Dichloro-5-sulfamoylbenzoic acid, 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. Product Details of 2736-23-4

SOCl2 (2.0 ml 28 mmol) was added dropwiseto a solution of 2,4-dichloro-5-sulfamoyl-benzoic acid 3 (1.50 g5.56 mmol) in DMF (4.3 ml) at 10 C. The reaction mixture wasstirred at room temperature for 2 h and then poured on ice; theresulted precipitate was filtered off and washed with water untilpH 7 was reached. Yield 77%, mp 254-255 C. 1H NMR d ppm:2.94 (3H, s, CH3N), 3.19 (3H, s, CH3N), 7.92 (1H, s,C3-H), 8.27 (1H,s,NC-H), 8.41 (1H, s,C6-H). 13C NMR d ppm: 35.8, 41.5, 130.2,132.1, 133.9, 134.6, 136.9, 139.1, 161.3, 165.2. HRMS calcd. for C10-H10Cl2N2O4S [(M+H)+]: 324.9811, found: 324.9814.

The synthetic route of 2,4-Dichloro-5-sulfamoylbenzoic acid has been constantly updated, and we look forward to future research findings.

Reference:
Article; ?apkauskait?, Edita; Zak?auskas, Audrius; Ruibys, Virginijus; Linkuvien?, Vaida; Paketuryt?, Vaida; Gedgaudas, Marius; Kairys, Visvaldas; Matulis, Daumantas; Bioorganic and Medicinal Chemistry; vol. 26; 3; (2018); p. 675 – 687;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 147291-66-5, These common heterocyclic compound, 147291-66-5, name is tert-Butyl 3-aminobenzylcarbamate, 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: The solution of EDCI (3.14g, 16.38mmol) and DMAP (100mg, 0.82mmol) in 10mL DCM was added dropwise to a mixture of tert-butyl-3-aminobenzyl-carbamate (2.0g, 9.01mmol) and benzoic acid (1.0g, 8.19mmol) in 20mL DCM at 0C under nitrogen atmosphere, and the mixture was warmed to r.t. and stirred overnight. After quenched with water and extracted with DCM, the organic layer was washed with 1M NaOH (20mL), 1M HCl (20mL), and saturated NaHCO3 (10mL), dried over Na2SO4, and concentrated under reduced pressure. The Boc-protected 12a was dissolved in DCM (5mL), trifluoroacetic acid (5mL) was added. The reaction mixture was allowed to stir for 2hat r.t. and concentrated under reduced pressure. The residue was purified by column chromatography over silica gel and further purified by recrystallization (ethyl ether) to obtain the title compound as a white solid (1.2g, yield 64.8%).

Statistics shows that tert-Butyl 3-aminobenzylcarbamate is playing an increasingly important role. we look forward to future research findings about 147291-66-5.

Reference:
Article; Zhao, Yaxue; Wang, Zhongli; Zhang, Jianchen; Zhou, Huchen; European Journal of Medicinal Chemistry; vol. 122; (2016); p. 178 – 184;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 459817-82-4, The chemical industry reduces the impact on the environment during synthesis 459817-82-4, name is tert-Butyl 1,2,3-oxathiazolidine-3-carboxylate 2,2-dioxide, I believe this compound will play a more active role in future production and life.

General procedure: To a 2M solution of isopropylmagnesium chloride (20 ml 0.040 mol) in diethyl ether was added 3-iodo benzotrifluoride (11.05 g 5.85 ml 0.040 mol) at -12C and the mixture was kept in the freezer (-20C) for 18h. To the resulting clear solution was added 0.100 g cuprous (I) iodide (0.00032 mol) and the mixture was stirred at room temperature for 2h. A clear slighthly yellow solution was obtained.To a suspension of the corresponding sulfamidate (2a-e) (0.0050 mol) in 5 ml diethyl ether was added drop wise 5.0 ml of the stock solution of m-(trifluoromethyl)phenylmagnesium chloride (ca 0.001 mol) as prepared above at -12C and the mixture was stirred at -12C for 2h. To the resulting suspension was added 10 ml of a 10% aqueous citric acid solution and the mixture was stirred at room temperature for 0.5h. The phases were separated and the organic phase was dried over magnesium sulfate and evaporated to dryness. The resulting residue was purified by kugelrohr distillation (0.4 mBar; 95C) or by recrystallisation from heptane as indicated in the table.

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 1,2,3-oxathiazolidine-3-carboxylate 2,2-dioxide, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Hebeisen, Paul; Weiss, Urs; Alker, Andre; Staempfli, Andreas; Tetrahedron Letters; vol. 52; 41; (2011); p. 5229 – 5233;,
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. 164332-88-1, name is tert-Butyl (2-(2-bromoethoxy)ethyl)carbamate, A new synthetic method of this compound is introduced below., Quality Control of tert-Butyl (2-(2-bromoethoxy)ethyl)carbamate

General procedure: A mixture of the alkyl halide, nitrogen-containing compound and excess base (NaH for compounds 80 and 81, Cs2CO3 for other compounds) in DMF was stirredat 60 C for 30 min. The reaction was quenched with water and extracted with EA. The organic layer was washed with water and brine, concentrated and purified by column chromatography.

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:
Article; Ngo, Van T.H.; Hoang, Van-Hai; Tran, Phuong-Thao; Ann, Jihyae; Cui, Minghua; Park, Gyungseo; Choi, Sun; Lee, Jiyoun; Kim, Hee; Ha, Hee-Jin; Choi, Kwanghyun; Kim, Young-Ho; Lee, Jeewoo; Bioorganic and Medicinal Chemistry; vol. 26; 5; (2018); p. 1035 – 1049;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics