Category: amides-buliding-blocks

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,
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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;,
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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,
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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,
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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,
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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

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

Synthetic Route of 194920-62-2, 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. 194920-62-2 name is tert-Butyl (3-(2-(2-(3-aminopropoxy)ethoxy)ethoxy)propyl)carbamate, 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 solution of 7 (10.8 g, 30.3 mrnol, 1.0 equiv) in DCM (400 mL) was treated at 4 C with triethylamine (5.29 mL, 37.9 minol, 1.3 equiv), followed by allyl chloroformate (3.56 mL, 33.4 rnmol, 1.1 equiv) . After 15 mm, the reaction was allowed to warm to room temperature and was stirred for 2 h. Then, the reaction mixturewas washed with water (3 x 250 mL), dried over MgSO4, filtered and concentrated under reduced pressure. The product waspurified by flash chromatography (200 g SiC2 ethylacetate/hexanes 1:1, then ethyl acetate) to give 8 (11.0 g, 90%)as a colorless oil.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, tert-Butyl (3-(2-(2-(3-aminopropoxy)ethoxy)ethoxy)propyl)carbamate, and friends who are interested can also refer to it.

Reference:
Patent; ETH ZURICH; CARREIRA, Erick, Moran; SCHAFROTH, Michael, Andreas; SOBOTZKI, Nadine; WOLLSCHEID, Bernd; (67 pag.)WO2017/81069; (2017); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

402-46-0, name is 4-Fluorobenzenesulfonamide, 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. HPLC of Formula: C6H6FNO2S

To a solution of 4-fluorobenzenesulfonamide (1 .02 g, 5.71 mmol) in H20 (10 mL) was added piperazine (2.46 g, 28.55 mmol). The reaction mixture was stirred at 100 00 overnight. The mixture was cooled to room temperature and filtered. The filtration cake was washed with H20 (20 mL), toluene(30 mL) and ether (30 mL) to give 26.1 (401 mg, 29% yield). MS (ESI) m/z = 242.0 [M¡ÂH]. 1H NMR (400 M, DMSO-c), oe 7.60 (d, J = 8.8 Hz, 2H), 7.05 (m, 2H), 7.00 (d, J = 8.8 Hz, 2H), 3.17 (m, 4H), 2.80 (m, 4H), 2.33 (m, 1H).

The synthetic route of 402-46-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UNITY BIOTECHNOLOGY, INC.; BACKES, Bradley; W. VON GELDERN, Thomas; CHEN, Bing; (121 pag.)WO2017/101851; (2017); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 21744-84-3, 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. 21744-84-3, name is 4-Methyl-2H-1,4-Benzoxazin-3-one belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of (2-chloro-5-methoxy-phenyl)-acetic acid (1 g) in tetrahydrofuran (20 ml) were added N,N-dimethylformamide (2 drops) and oxalylchloride (1.03 g). The mixture was stirred overnight at room temperature. The solvent was evaporated; toluene was added and again evaporated. The residue was dried under high vacuum to give the crude acid chloride. To a cooled solution (ice bath) of 4-methyl-2H-1,4-benzoxazin-3(4H)-one (830 mg) in 1,2-dichloroethane (5 ml) was added AlCl3 (1.99 g). The mixture was stirred for 10 min and a solution of the acid chloride in 1,2-dichloroethane (5 ml) was added dropwise. The mixture was stirred at 0 C. for 4.5 h. The mixture was poured into ice water and hydrochloric acid and extracted with dichloromethane. The organic phase was dried (MgSO4), filtered and concentrated. The product was purified by chromatography (SiO2, cyclohexane/EtOAc 1_0=>0:1) to give the title compound (1.6 g) as an off-white solid. MS (m/e)=346.1 [M+H-].

The synthetic route of 4-Methyl-2H-1,4-Benzoxazin-3-one has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hunziker, Daniel; Lerner, Christian; Mueller, Werner; Sander, Ulrike Obst; Pflieger, Philippe; Waldmeier, Pius; US2010/249124; (2010); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics