Month: February 2021

Adding a certain compound to certain chemical reactions, such as: 33045-52-2, name is Methyl 2-methoxy-5-sulfamoylbenzoate, 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 33045-52-2, HPLC of Formula: C9H11NO5S

Methyl 2-methoxy-5-sulfamoylbenzoate(4.91g, 20mmol) was dissolved in methanol(30mL). 2N Aqueous sodium hydroxide(30mL, 60mmol) was added, and the mixture was stirred at room temperature for 1 hour. The reaction mixture was poured into 2N hydrochloric acid, and the separated solid was filtered to give the title compound(4.55g, 98.3%) as a white solid.1H-NMR(DMSO-d6): delta 3.89(3H, s), 7.30(1H, d, J=8.7Hz), 7.32(2H, s), 7.92(1H, dd, J=8.7, 2.7Hz), 8.09(1H, d, J=2.7Hz), 13.03(1H, br).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Institute of Medicinal Molecular Design, Inc.; EP1514544; (2005); 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. 459817-82-4, name is tert-Butyl 1,2,3-oxathiazolidine-3-carboxylate 2,2-dioxide, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 459817-82-4

Step 1: tert-butyl (2-(2-bromo-4-chloropyridin-3-yl)ethyl)carbamate. 94-1 To a stirred solution of LDA (5.98 mmol) in THF (50 mL) 2-bromo-4-chloropyridine (1.0 g, 5.20 mmol) was added at -70 C. and the resulting solution was stirred at -70 C. for 1 h. Then a solution of tert-butyl 1,2,3-oxathiazolidine-3-carboxylate 2,2-dioxide (1.39 g, 6.24 mmol) in THF (20 mL) was added at -70 C. and the reaction mixture was stirred for 3 h. Saturated aqueous NH4Cl solution was added at -70 C. and the mixture was allowed to warm to RT. The mixture was extracted with AcOEt (2*). The combined organic layers were washed with brine, dried with sodium sulfate, filtered and the solvent was removed under reduced pressure. The crude product was purified by flash-column chromatography over silicagel (Biotage Isolera One, eluent: gradient from 2% MeOH in DCM to 13% MeOH in DCM in 12 min) to yield the title compound as a white solid (1.36 g). UPLC-MS: MS 335.1 (M+H+); UPLC rt 1.06 min.

According to the analysis of related databases, 459817-82-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NOVARTIS AG; BEHNKE, Dirk; CARCACHE, David; ERTL, Peter; KOLLER, Manuel; ORAIN, David; US2014/57902; (2014); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 117009-97-9, These common heterocyclic compound, 117009-97-9, name is Benzyl 1,4-diazepane-1-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.

Synthesis of 4-(1-chloro-8-propoxy-isoquinoline-5-sulfonyl)-[1,4]diazepane-1-carboxylic acid benzyl ester (7) A solution of 1-chloro-8-propoxy-isoquinoline-5-sulfonic acid (5) and 1-chloro-8-propoxy-isoquinoline-7-sulfonic acid (6) (476 mg, 1.58 mmol) in SOCl2 (5 ml) and DMF (0.5 ml) was heated at 80 C for 2 h. The solvent was evaporated. The residue was quenched with H2O and the solution was neutralized (pH = 8) by addition of a saturated NaHCO3 solution. The mixture was extracted with CH2Cl2. The combined organic layers were poured drop wise to a solution of Cbz-homopiperazine (490 mg, 2.09 mmol) in CH2Cl2 (5 ml) at 0 C. The reaction was stirred at 0 C for 2 h. The reaction was washed with water. The organic layers were dried over MgSO4, concentrated and purified by flash chromatography (cyclohexane/EtOAc 10/0 to 8/2) to afford 360 mg (44%) of 4-(1-chloro-8-propoxy-isoquinoline-5-sulfonyl)-[1,4]diazepane-1-carboxylic acid benzyl ester (7) as a yellow oil. 1H NMR (300 MHz,DMSO-d6) delta : 8.37-8.18 (m, 3H), 7.25 (m, 5H), 6.91 (d, J = 8.6 Hz, 1H), 5.02 (s, 2H), 4.13 (t, J = 6.1 Hz, 2H), 3.54-3.46 (m, 4H), 3.36-3.27 (m, 4H), 1.97-1.80 (m, 4H), 1.19 (t, J = 7.1 Hz, 3H).

Statistics shows that Benzyl 1,4-diazepane-1-carboxylate is playing an increasingly important role. we look forward to future research findings about 117009-97-9.

Reference:
Patent; Sygnis Bioscience GmbH & Co. KG; EP2332917; (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. 154748-63-7, name is tert-Butyl (3-hydroxycyclobutyl)carbamate, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C9H17NO3

To a solution of (3-hydroxy-cyclobutyl)-carbamic acid tert-butyl ester (2.5 g, 13.3 mmol) in THF (40 mL) were added CS2CO3 (8.6 g, 26.6 mmol) and 5-bromo-2,4- dichloro- pyrimidine (3 g, 13.3 mmol). The reaction mixture was heated at reflux overnight. The reaction mixture was filtered and concentrated, diluted with EtOAc and water. The aqueous phase was extracted with EtOAc (3 x 100 mL) and the combined organic extracts were washed with brine (60 mL), dried over MgSO*}, filtered, and concentrated. Purification by flash column chromatography on silica gel to give the product (4.75 g, 12.6 mmol, yield: 95%). ESI-MS (M+l): 378 calc. for CisHnBrClNsOs 377.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 154748-63-7.

Reference:
Patent; AMGEN INC.; ALLEN, Jennifer; FROHN, Michael; HARRINGTON, Paul; PICKRELL, Alexander; RZASA, Robert; SHAM, Kelvin; HU, Essa; WO2011/143366; (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. 53250-82-1, name is 4-(Methylsulfonamido)aniline, A new synthetic method of this compound is introduced below., SDS of cas: 53250-82-1

Example 46 (2464) N-(4-((7-Chloro-5-hydroxy-1 ,1 -dioxido-2H-benzore1H ,2,41thiadiazin-3- yl)amino)phenyl)methanesulfonamide (2465) (2466) To a stirred solution of N-(4-aminophenyl)methanesulfonamide (143 mg), KH2P04 (105 mg) in t-BuOH (10 mL) at 0 C was added 3-bromo-7-chloro-5-hydroxy-4H- benzo[e][1 ,2,4]thiadiazine 1 ,1 -dioxide (lnt-3, 200 mg) in portions. The reaction mixture was then stirred at 80 C for 16 hr, cooled to RT, and diluted with cold water. The resulting solid was collected by filtration, washed with diethyl ether and dried under vacuum to afford the titled compound (177.7 mg). LCMS m/z 416.92 (M+H). NMR after D20 exchange (400 MHz, DMSO-c/e) delta ppm 2.97 (s, 3 H) 7.09 (d, J=1 .97 Hz, 1 H) 7.18 (d, J=2.19 Hz, 1 H) 7.25 (d, J=8.77 Hz, 2 H) 7.48 (d, J=8.77 Hz, 2 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; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; ADAMS, Jerry Leroy; ATOR, Laura E.; DUFFY, Kevin J.; GRAYBILL, Todd L.; KIESOW, Terence John; LIAN, Yiqian; MOORE, Michael Lee; RALPH, Jeffrey M.; RIDGERS, Lance Howard; (370 pag.)WO2017/98421; (2017); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 239074-29-4, name is tert-Butyl (trans-4-(hydroxymethyl)cyclohexyl)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 239074-29-4, SDS of cas: 239074-29-4

To a stirred solution of tert-butyl ((1R,4R)-4-(hydroxymethyl)cyclohexyl)carbamate (1.5 g, 0.7 mmol, synthesized via Steps 1-2 of Intermediate K) and 1-phenyl-2,5,8,11,14-pentaoxahexadecan-16-yl 4-methylbenzenesulfonate (4.74 g, 0.98 mmol, Intermediate X) in THF (30 mL) was added KOH (3.67 g, 65.4 mmol) at rt. The resulting reaction mixture then heated to 60 C. and stirred for 16 h. The reaction mixture was then transferred into ice water and the resulting mixture was extracted using ethyl acetate (3¡Á100 mL). The combined organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was evaporated under reduced pressure and the crude product was purified using silica gel column chromatography (2% MeOH-DCM) to give tert-butyl ((1R,4R)-4-(18-phenyl-2,5,8,11,14,17-hexaoxaoctadecyl)cyclohexyl)carbamate as a yellow oil (0.92 g, 26%). LC-MS (ESI+) m/z 557.4 (M+18)+.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Kymera Therapeutics, Inc.; Mainolfi, Nello; Ji, Nan; Kluge, Arthur F.; Weiss, Matthew M.; Zhang, Yi; (1443 pag.)US2019/192668; (2019); 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. 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

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

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

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., name: 4-Amino-2-fluoro-N-methylbenzamide

The mixture of 4-amino-2-fluoro-Nmethylbenzamide(22) (1.68 g, 10 mmol) [35], H2SO4 (0.68 mL) andwater (13 mL) was gently heated until all the components werecompletely dissolved. The mixture was cooled to 0e5 understirring, then the solution of NaNO2 (0.7 g,10 mmol) inwater (2 mL)was added dropwise. The resulting mixture was stirred at 0e5for 0.5 h and then slowly poured into the solution of KI (5 g) in coldwater (20 mL). The solutionwas then heated up to 80 and stirredfor 0.5 h. After cooling it was treated with 30 mL of chloroform andfiltered. The organic layer was washed with 5% Na2SO3 solution,dried over Na2SO4 and rotovapped. Column chromatography onsilica gel (hexane/EtOAc 6:1) afforded 2.33 g (83%) of 2-fluoro-4-iodo-N-methylbenzamide (37). MS (ESI) [MH] 280. 1H NMR(400 MHz, DMSO-d6) d 8.25 (m, 1H), 7.73 (d, J 10.0 Hz, 1H), 7.65 (d,J 7.8 Hz, 1H), 7.37 (t, J 7.8 Hz, 1H), 2.75 (d, J 4.4 Hz, 3H). Thesolution of compound 37 (9 g, 32 mmol) in DMF (25 mL) was addedto the ice cooled suspension of NaH (1.48 g, 36.8 mmol, 60% in oil,washed with hexane) in DMF (50 mL). The resulting mixture wasvigorously stirred for 0.5 h in an ice bath, then SEM-chloride (6.46 g,39 mmol) was added and the mixture was continuously stirredovernight at the ambient temperature. After the reaction wascompleted, the mixture was poured into water (400 mL) and theobtained product was extracted with benzene (2 200 mL),washed with water, dried over Na2SO4 and then filtered through3 cm layer of silica gel washing with 5:1 hexane/EtOAc. The solventwas evaporated in vacuo providing 11 g (84%) of 2-fluoro-4-iodo-Nmethyl-N-[2-(trimethylsilyl)ethoxymethyl]benzamide (40). MS(ESI) [MH] 520. 1H NMR (400 MHz, CDCl3) d 7.58 (m,1H), 7.52 (m,1H), 7.12 (m, 1H), 5.01 (s, 0.8H), 4.58 (s, 1.2H), 3.63 (t, J 8.2 Hz,0.8H), 3.31 (t, J 8.2 Hz, 1.2H), 3.14 (s, 1.8H), 2.92 (d, J 0.8 Hz,1.2H), 0.99 (t, J 8.2 Hz, 0.8H), 0.82 (t, J 8.2 Hz, 1.2H), 0.04 (s,3.6), 0.01 (s, 5.4). The mixture of 6.69 g (51 mmol) of aminoacid(R)-36a or 9.55 g of (R)-36b, 17.4 g (42.5 mmol) of 40, 1.62 g(8.5 mmol) of CuI, 23.5 g (0.17 mol) of K2CO3, 36mL of water,145mLof DMF and 3e5 drops of Et3N was stirred for 10 min, then 6.56 g (46.8 mmol) of 2-acetylcyclohexanone was added and stirringcontinued at 100 for 24 h. After cooling the mixture was rotovapped,the residue was treated with 200mL of water and acidifiedwith hydrochloric acid to 2e3 (~30 mL). Then 200 mL of etherwas added, the mixture was stirred for 0.5 h and the formed precipitatewas filtered off, washed with 50 mL of ether and dried invacuo to give 10.7 g (65%) of (R)-3-(3-fluoro-4-{methyl[2-(trimethylsilyl)ethoxymethyl]carbamoyl}phenylamino)-tetrahydrofuran-3-carboxylic acid ((R)-41) (55% from ester (R)-36b). MS (ESI)[MH] 413. 1H NMR (400 MHz, DMSO-d6) d 12.97 (brs, 1H), 7.07(m, 2H), 6.31 (brs, 1H), 6.17 (brs, 1H), 4.85 (brs, 0.67H), 4.60 (brs,1.33H), 4.10 (brs, 1H), 3.87 (brs, 3H), 3.51 (brs, 0.67H), 3.24 (brs,1.33H), 2.93 (s, 2H), 2.86 (brs, 1H), 2.56 (brs, 1H), 2.16 (brs, 1H), 0.89(brs, 0.67H), 0.73 (brs, 1.33H), 0.03 (m, 9H). The mixture of 10.7 g(26 mmol) of (R)-41 and 8.9 g (39 mmol) of 4-isothiocyanato-2-(trifluoromethyl)benzonitrile (42) [34] in pyridine (100 mL) wasstirred at 80 for 48 h. The residue formed after cooling androtovapping was then treated with ethyl acetate and filteredthrough 2 cm layer of silica gel. The solvent was removed underreduced pressure and the desired product was crystallized fromethanol to obtain 4.85 g (30%) of 4-{(R)-3-[4-cyano-3-(trifluoromethyl)phenyl]-4-oxo-2-thioxo-7-oxa-1,3-diazaspiro[4.4]non-1-yl}-2-fluoro-N-methyl-N-[2-(trimethylsilyl)ethoxymethyl]benzamide ((R)-43). MS (ESI) [MH] 623. 1H NMR (400 MHz,CDCl3) d 8.01 (d, J 8.0 Hz, 1), 7.98 (s, 1), 7.85 (d, J 8.0 Hz, 1),7.57 (m, 1), 7.28 (m, 1), 7.21 (m, 1), 5.06 (s, 0.8), 4.63 (s, 1.2),4.41 (d, J 10.4 Hz, 1), 4.16 (d, J 10.4 Hz, 1), 3.97 (q, J 7.6 Hz,1), 3.78 (m, 1), 3.66 (t, J 8.2 Hz, 0.8), 3.66 (t, J 8.2 Hz, 1.2),3.20 (s, 1.8), 2.99 (s, 0.8), 2.72 (m, 1), 2.47 (m, 1), 1.01 (t,J 8.2 Hz, 0.8), 0.83 (t, J 8.2 Hz, 1.2), 0.06 (s, 3.6), 0.01 (s,5.4). TFA (15 mL) was added to the solution of compound (R)-43(4.8 g, 7.7 mmol) in DCM (30 mL), then the resulting mixture wasstirred for 3 h. The solvent was removed under reduced pressureand the formed residue was subjected to column chromatographyon silica gel (CHCl3/MeOH 60:1) to give 2.96 g (78%) of desiredproduct (R)-6.

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; Ivachtchenko, Alexandre V.; Ivanenkov, Yan A.; Mitkin, Oleg D.; Vorobiev, Anton A.; Kuznetsova, Irina V.; Shevkun, Natalia A.; Koryakova, Angela G.; Karapetian, Ruben N.; Trifelenkov, Andrey S.; Kravchenko, Dmitry V.; Veselov, Mark S.; Chufarova, Nina V.; European Journal of Medicinal Chemistry; vol. 99; (2015); p. 51 – 66;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics