Month: December 2020

Adding a certain compound to certain chemical reactions, such as: 127828-22-2, name is tert-Butyl (2-(2-aminoethoxy)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 127828-22-2, Application In Synthesis of tert-Butyl (2-(2-aminoethoxy)ethyl)carbamate

tert-Butyl 2-(2-aminoethoxy)ethylcarbamate (300 mg, 1.47 mmol) was taken up in CH2Cl2 (15 mL) along with 2-(4-(4-chlorobenzoyl)phenoxy)-2-methylpropanoic acid (fenofibric acid, 467 mg, 1.47 mmol) and EDCI (310 mg, 1.47 mmol). The resulting reaction mixture was stirred at room temperature for 18 h. It was then brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (9:1 CH2Cl2/MeOH) to afford tert-butyl 2-(2-(2-(4-(4-chlorobenzoyl)phenoxy)-2-methylpropanamido)ethoxy)ethylcarbamate (260 mg, 35%).

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

Reference:
Patent; Milne, Jill C.; Jirousek, Michael R.; Bemis, Jean E.; Vu, Chi B.; US2011/82210; (2011); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 193751-54-1, 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. 193751-54-1, name is tert-Butyl cyclopent-3-en-1-ylcarbamate, This compound has unique chemical properties. The synthetic route is as follows.

6.63 g of mCPBA (70%) was added at 0C to a solution of 4.7 g of N-Boc-cyclopent-3-enyl amine in 80 mL of DCM. The solution obtained was stirred at rt for 1.5 h, charged with 20 mL of 20% sodium thiosulfate, stirred for 10 min, DCM was added, phases obtained were separated and the organic layer obtained was washed with saturated NaHC03 solution. The aqueous layer obtained was extracted twice with DCM, the combined organic layers obtained were dried over magnesium sulfate and solvent was evaporated. 5.2 g of the crude product was obtained which was recrystallized twice from heptane. 917 mg of syn epoxide was obtained in the form of white needles. The mother liquors obtained were subjected to chromatography (silica, toluene/EtOAc = 9: 1 – 7: 1). 3.51 g of anti epoxide in the form of a white amorphous solid was obtained.Syn epoxide: NMR (400MHz, DMSO-d6, delta, ppm, characteristic signals): 1.36 (s, 9H), 6.79 (d, 1H, J=8Hz), 1.47 (dd, 1H, J=8Hz and 14Hz), 2.17 (dd, 1H, J=8Hz and 14Hz), 3.44 (s, 2H), 3.54 (m, 1H). MS-ESI+ (m/z): 200 (M + H). TLC: toluene/EtOAc = 3:1, Rf = 0.4.Anti epoxide: 1H NMR (400MHz, DMSO-d6, delta, ppm, characteristic signals): 1.35 (s, 9H), 1.78 (d, 2H, J=15Hz), 1.98 (dd, 1H, J=8Hz and 15Hz), 3.51 (s, 2H), 3.89 (q, 1H, J=8 and 16Hz), 5.70 (d, 1H, J=8Hz). MS-ESI+ (m/z): 200 (M + H). TLC: toluene/EtOAc = 3: 1, Rf = 0.45.

The chemical industry reduces the impact on the environment during synthesis tert-Butyl cyclopent-3-en-1-ylcarbamate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; NABRIVA THERAPEUTICS AG; RIEDL, Rosemarie; THIRRING, Klaus; HEILMAYER, Werner; WO2012/31307; (2012); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Related Products of 749927-69-3, These common heterocyclic compound, 749927-69-3, name is 4-Bromo-2-fluoro-N-methylbenzamide, 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 stirred suspension of zinc powder (2.5 g, 38.5 mmol) in anhydrous N,N-d m ethyl form a ide (10 mL) under nitrogen was added iodine (200 mg). After 5 min, a solution of methyl (f?)-2-((/er/-butoxycarbonyl)amino)-3-iodopropanoate (5.0 g, 15.2 mmol) in A( A’-di m ethyl form a i de (10 mL) was added slowly over lOmin. The mixture was stirred at rt for 30min. A suspension of 4-bromo-2-fluoro-Af- methylbenzamide (2.8 g, 12 mmol), Pd2(dba)3 (280 mg, 0.3 mmol), and 2- dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (Sphos, 250 mg, 0.6 mmol) in /V,/V- dimethylformamide (10 mL) was added into the zinc reagent mixture. The reaction mixture was heated at 50C and stirred overnight. After cooling, the reaction mixture was quenched with water, diluted with EtOAc and filtered through Celite. The filter cake was washed with EtOAc and the filtrate was washed with brine, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by flash column chromatography over silica gel (0-80% EtO Ac/hexane) to afford the desired product as a beige solid (4.0 g, 94%). LC-MS: 377.1 [M+Na]+; 1H NMR (400MHz, CDCl3) d 8.04 (t, 1H, J = 8.1 Hz), 7.02 (d, 1H, J = 8.0 Hz), 6.91 (d, 1H, J = 12.8 Hz), 6.70 (m, 1H), 5.02 (d, 1H, J = 8.0 Hz), 4.60 (m, 1H), 3.73 (s, 3H), 3.18 (dd, 1H, J = 13.8, 5.4 Hz), 3.07 (m, 1H), 3.03 (d, 3H, J = 4.6 Hz), 1.43 (s, 9H).

The synthetic route of 749927-69-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; EPIODYNE, INC.; MEDINA, Julio Cesar; MCGEE, Larry; WEI, Zhi-Liang; SADLOWSKI, Corinne; SEIDL, Frederick; BHATT, Ulhas; WANG, Xiaodong; NGUYEN, Thomas; SPERANDIO, David; DING, Pingyu; NERURKAR, Alok; LI, Yihong; DUQUETTE, Jason; (307 pag.)WO2019/195634; (2019); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

These common heterocyclic compound, 6228-73-5, name is Cyclopropanecarboxamide, 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: C4H7NO

To a suspension of 17 (2.00 g, 23.5 mmol) in n-BuOAc (20 mL) at 40-50 C was added 2-bromoacetyl bromide 18b (5.23 g, 25.9 mmol) dropwise, and the mixture was heated to 80 C and stirred for 5 min. After cooling to room temperature, the mixture was stirred for 0.5 h, and then filtered. Wet solids were washed with n-BuOAc (5 mL) and dried in vacuo at 60 C to give the title compound 14b (1.73 g, 36%) as a white solid; mp 153-154 C; 1H NMR (500 MHz, DMSO-d6) delta 0.84-0.88 (m, 2H), 0.89-0.93 (m, 2H), 2.02-2.07 (m, 1H), 4.33 (s, 2H), 11.27 (s, 1H); 13C NMR (125 MHz, DMSO-d6) delta 9.2 (2C), 14.2, 31.7, 167.0, 173.9; IR (ATR) 3255, 3174, 3018, 2947, 1741, 1697, 1513, 1450, 1392, 1283, 1175, 1144, 1103, 1059, 1025, 972, 937, 886, 848, 824, 797, 701, 581, 551, 419 cm-1; Anal. Calcd for C6H8NO2Br; C, 34.98; H, 3.91; N, 6.80; Br, 38.78. Found: C, 34.83; H, 3.78; N, 6.80; Br, 38.95.

The synthetic route of Cyclopropanecarboxamide has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ishimoto, Kazuhisa; Sawai, Yasuhiro; Fukuda, Naohiro; Nagata, Toshiaki; Ikemoto, Tomomi; Tetrahedron; vol. 69; 40; (2013); p. 8564 – 8571;,
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. 39945-54-5, name is Benzyl (3-bromopropyl)carbamate, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C11H14BrNO2

Step B N-Benzyloxycarbonyl-N-methyl-3-bromopropylamine N-Benzyloxycarbonyl-3-bromopropylamine (from Step A; 1.0 g, 3.68 mM) was dissolved in dry THF (4 mL) and methyl iodide (522 mg, 3.68 mM) was added. After cooling to 0 C., potassium t-butoxide (3.68 mL of a 1M solution in THF) was added dropwise to the reaction mixture. The crude reaction mixture was filtered over a pad of Celite and washed through with ether. The combined filtrate and washings were concentrated under reduced pressure. The residue was flash chromatographed over 125 mL silica gel, eluding with 8:1 hexane-EtOAc, to give 890 mg pale yellow liquid, homogeneous on TLC in 80:20 hexane-EtOAc; 1 H-NMR (300 MHz, CDCl3, ppm) delta2.06 (m, 2H), 2.94 (s, 3H), 3.38 (m, 4H), 5.11 (s, 2H), 7.34 (m, 5H). Mass spectrum (FAB) m/e 288 (M+1)+.

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 39945-54-5.

Reference:
Patent; Merck & Co., Inc.; US5411980; (1995); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Related Products of 209917-48-6, A common heterocyclic compound, 209917-48-6, name is N-tert-Butyl 4-Aminophenylsulfonamide, molecular formula is C10H16N2O2S, 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.

N-(tert-butyl)-4-((5,ll-dimethyl-6-oxo-6,ll-dihydro-5H-benzo[e]pyrido[3,2- b ] [ 1 ,4] diazepin-2-yl)amino)benzenesulf onamide 2-Chloro-5,l l-dimethyl-5H-benzo[e]pyrido[3,2-b][l,4]diazepin-6(l lH)-one (17.2 mg, 0.0628 mmol, 1 eq), 4-amino-N-(/ert-butyl)benzenesulfonamide (17.2 mg, 0.0754 mmol, 1.2 eq), Pd2dba3 (2.9 mg, 0.00314 mmol, 5 mol%), XPhos (4.5 mg, 0.00942 mmol, 15 mol%) and potassium carbonate (34.7 mg, 0.251 mmol, 4 eq) were dissolved in tBuOH (0.63 mL, 0.1M) and heated to 100 C for 23 hours. The mixture was filtered through CELITE, washed with DCM/MeOH and concentrated under reduced pressure. Purification by column chromatography (ISCO, 12 g column, 0-10%MeOH/DCM, 15 minute gradient) gave the desired product as a yellow solid (24.79 mg, 0.0532 mmol, 84%). 1H NMR (400 MHz, Chloroform-J) delta 7.85 – 7.77 (m, 3H), 7.57 (d, J = 8.8 Hz, 2H), 7.38 (t, J = 8.5 Hz, 2H), 7.09 (dd, J = 7.8, 2.1 Hz, 2H), 6.72 (s, 1H), 6.58 (d, J = 8.5 Hz, 1H), 4.44 (s, 1H), 3.48 (s, 3H), 3.38 (s, 3H), 1.25 (s, 9H). 13C NMR (100 MHz, cdcl3) delta 168.67, 155.72, 151.67, 149.25, 144.22, 134.99, 132.95, 132.20, 131.97, 128.49, 126.92, 123.89, 123.13, 117.15, 116.82, 105.58, 54.52, 37.66, 36.11, 30.20. LCMS 466.47 (M+H).

The synthetic route of 209917-48-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DANA-FARBER CANCER INSTITUTE, INC.; BRADNER, James, E.; GRAY, Nathanael; QI, Jun; MCKEOWN, Michael, R.; BUCKLEY, Dennis; WO2015/117083; (2015); 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. 1195768-19-4, name is Methyl 3-(2,6-difluorophenylsulfonamido)-2-fluorobenzoate, This compound has unique chemical properties. The synthetic route is as follows., category: amides-buliding-blocks

A solution of Lithium bis(trimethylsilyl)amide (1M in THF, 4.05mL, 4.05mmol) was added to a cooled (0C) solution of Methyl 3-((2,6-difluorophenyl)sulfonamido)-2- fluorobenzoate (400mg, 1.16mmol) in THF (3mL). After lOmin of stirring, a solution of 2-chloro-4-methylpyrimidine (178mg, 1.39mmol) in THF (2mL) was slowly added and the reaction mixture was allowed to warm to room temperature for 2h. Aqueous saturated ammonium chloride was added to the medium. The aqueous layer was extracted with EtOAc (2 times). Combined organics were washed with brine, dried over sodium sulphate, filtered and the filtrate was concentrated under reduced pressure. Trituration of the brown solid in DCM/cHex afforded title compound (420mg, 82%) as a mixture of ketone and enol. LC/MS (ES+): 442.0-444.0 (M+l).

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 1195768-19-4.

Reference:
Patent; CELLIPSE; PRUDENT, Renaud; PAUBLANT, Fabrice; (74 pag.)WO2018/55097; (2018); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 563-83-7, 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 563-83-7 as follows.

A. 2-Methylpropanethioamide Phosphorus pentasulfide (3.25 g, 14.6 mmol) was added to a solution of 2-methylpropanamide (5.00 g, 57.4 mmol) in diethyl ether/benzene (2:1; 150 mL). The mixture was stirred for 2.5 h at room temperature to give a tacky yellow solid and a supernatant layer. The supernatant was filtered through Celite and the tacky yellow solid was extracted with diethyl ether (3*25 mL) and the extracts were filtered through Celite. The combined organic layers were evaporated to give 2-methylpropanethioamide (4.6 g, 78% yield) as a yellow oil that solidified on standing.

According to the analysis of related databases, 563-83-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Fotouhi, Nader; Gillespie, Paul; Guthrie, Robert William; Pietranico-Cole, Sherrie Lynn; Yun, Weiya; US2002/161237; (2002); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

78191-00-1, name is N-Methoxy-N-methylacetamide, 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. Application In Synthesis of N-Methoxy-N-methylacetamide

Toluene-4-sulfonic acid 6-bromo-pyridin-3-yl ester (XVI) (980 mg, 2.99 mmol) was dissolved in tetrahydrofuran (THF) (3 mL) and the resulting solution was cooled to -78 C. 2.0 M lithium diisopropylamide (LDA) (2.24 mL, 4.48 mmol) dissolved in tetrahydrofuran was slowly added dropwise to the solution and the solution was stirred at -78 C for 3 hrs. And then, N-methoxy-N-methyl acetamide (609.77 muL, 5.97 mmol) was slowly added dropwise to the solution and the solution was stirred for 2 hrs. Saturated sodium hydrogen carbonate (NaHCO3) solution was added dropwise to the solution and the solution was diluted with ethylacetate (EA). Then, the organic solvent was dried over anhydrous magnesium sulfate (MgSO4), filtered, and evaporated under reduced pressure to concentrate. The resulting residue was isolated and purified by silica gel column chromatography (n-Hex/EA = 4/1) to give the title compound (570 mg, 52 %). 1H NMR (400 MHz, CDCl3) delta 7.97 (s, 1H), 7.70 (d, J = 8.0 Hz, 2H), 7.65 (s, 1H), 7.37 (d, J = 8.0 Hz, 2H), 2.58 (s, 3H), 2.49 (s, 3H).

The synthetic route of 78191-00-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Beyondbio Inc.; MIN, Changhee; OH, Byungkyu; KIM, Yongeun; PARK, Changmin; (98 pag.)EP3255042; (2017); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 202207-79-2, 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. 202207-79-2, name is 1-(Boc-amino)-2-(methylamino)ethane Hydrochloride belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

3-Chloro-5- { [2-oxo- 1 -( lH-pyrazolo[3 .4-&]pyridin-3-ylmethyl)-4-(trifluoromethyl)-l,2-dihydropyridin-3-yl)oxy}benzonitrile_(6.0 g, 13.46 mmol) was stirred in DMA (140 mL) until dissolved and then cooled over ice bath for 10 minutes. This solution was treated with diisopropylethylamme (4.70 mL, 26.9 mmol) and then 4-nitrophenyl chloroformate (3.26 g, 16.15 mmol) portionwise over 5 minutes. This mixture was allowed to warm to room temperature and then stirred for 30 minutes. Formation of the intermediate carbamate was monitored by queching a small aliquot of the reaction mixture with dimethylamine and monitoring by LC-MS. The reaction mixture was then recooled over an ice bath and the cooled mixture was treated with a solution of 2-[(/er/-butoxycarbonyl)amino]-N-methylethanaminium chloride (3.40 g, 16.15 mmol) and diisopropylethylamme (2.5 mL, 14.3 mmol) in DMA (35 mL). Upon completion of addition, the cooling bath was removed and the mixture stirred for 1 hour at room temperature. This mixture was partitioned between ethyl acetate (1000 mL and 500 mL) and water (500 mL). The combined extracts were further washed with water (3x 00 mL), dried over MgS04, filtered and the solvent removed by evaporation in vacuo. This residue was pre- absorbed onto silica gel (35 g) using ethyl acetate and purified by silica gel (330 g)chromatography eluting with 0-100% ethyl acetate in hexanes. The desired fractions were combined and then solvent was removed by evaporation in vacuo. The resulting residue was further purified by re-crystallizing from ethyl acetate (75 mL) to give the title compound as a white solid. lH NMR (CDCI3) delta-8.68 (d, 1H), 8.26 (d, 1H, J = 7 Hz), 7.72 (d, 1H), 7.39 (dd, 1H, J=1.5Hz), 7.30 (dd, 1H5 3=4.6 and 8Hz), 7.16 (dd, 1H, J=2Hz), 7.02 (dd, 1H, J=1.3 and 2.3 Hz), 6.46 (d, 1H, J=7 Hz), 5.18 (bs t, 1H), 5.50 (s, 2H), 3.7 (br, 2H), 3.52 (br, 2H), 3.17 (s, 3H) and 1.44 (s, 9H) ppm. LRMS (M+l): 646.1

The synthetic route of 1-(Boc-amino)-2-(methylamino)ethane Hydrochloride has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; JOLLY, Samson, M.; ANTHONY, Neville; GOMEZ, Robert; DUBOST, David, C.; WOODWARD, Rick, G.; WO2011/126969; (2011); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics