Author: Jessica.F

156731-40-7, name is 1-(Boc-amino)-3-butene, 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. COA of Formula: C9H17NO2

Sodium hydride (583 mg of 60% dispersion in mineral oil, 14.6 mmol) was washed twice with 16 mL portions of hexane and suspended in 16 mL anhydrous THF. Reaction mixture was cooled to 0C and tert-butyl but-3-enylcarbamate (830 mg, 4.85 mmol) was added dropwise. Reaction mixture was warmed up to room temperature and stirred under argon for 30 min. Reaction mixture was cooled to 0C and freshly distilled ethyl iodide (0.78 mL, 9.7 mmol) was added dropwise. Reaction mixture was allowed to warm up to room temperature overnight, and it was then cooled to 0C and quenched with saturated ammonium chloride solution. The layers were separated and aqueous layer was extracted with Et2O. Organics were combined and washed with saturated NaCl solution, dried over MgSO4 and concentrated under reduced pressure. Crude reaction mixture was purified by flash column chromatography (hexanes:EtOAc 4:1) to give 900 mg (93%) of the title compound as a colorless oil. IR (neat) 3078, 2976, 2932, 2871, 1685 cm-1; 1H NMR (300 MHz, CDCl3): delta [ppm] 1.04-1.09 (t, 3H, J=7.1 Hz), 1.42 (s, 9H), 2.20-2.27 (m, 2H), 3.19 (br m, 4H), 4.95-5.06 (m, 2H), 5.67-5.81 (m, 1H); 13C NMR (75 MHz, CDCl3): delta [ppm] 11.58, 26.45, 31.25, 39.90, 44.32, 77.01, 114.33, 133.62, 153.36; m/z (relative intensity) 199(1), 158(5), 102(8), 57(100), 41(70), 29(52). Anal.Calcd. for C11H21NO2: C, 66.29; H, 10.62; O, 16.06. Found: C, 66.07; H, 10.66; O, 15.95.

The synthetic route of 156731-40-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; McMills, Mark C.; Humes, Ross J.; Pavlyuk, Oksana M.; Tetrahedron Letters; vol. 53; 7; (2012); p. 849 – 851;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 711007-44-2, These common heterocyclic compound, 711007-44-2, name is 2,3-Diaminobenzamide, 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.

Cbz-glycine (2.92 g, 13.89 mmol) and 120 mL of acetonitrile were added to a 250 mL reaction flask, stirred and dissolved, and CDI (2.57 g, 15.85 mmol) was slowly added, and reacted at 45 C for 1.5 hours. After the reaction of the material was monitored by TLC (dichloromethane:methanol = 10:1), Intermediate VII (2 g, 13.23 mmol) was added and reacted at 45 C for 4 hours. TLC (dichloromethane: methanol = 10:1) monitoringAfter the raw materials are reacted, a large amount of white solid is produced, suction filtered, and dried. It was added to a 100 mL reaction flask, 50 mL of glacial acetic acid was added, and the reaction was refluxed at 120 C. After the reaction of the material was monitored by TLC (dichloromethane:methanol = 10:1), the glacial acetic acid was concentrated under reduced pressure and dissolved in 100 mL of water.Extracted with ethyl acetate (100 mL ¡Á 2), and the organic layer was combined.Wash with saturated sodium chloride (150 mL) and dry over anhydrous sodium sulfate. Filtered off with suction, the filtrate was concentrated to give the crude product (VIII) 4.18g, yield 97.4%.

Statistics shows that 2,3-Diaminobenzamide is playing an increasingly important role. we look forward to future research findings about 711007-44-2.

Reference:
Patent; China Pharmaceutical University; Xu Yungen; Zhu Qihua; Ge Yiran; Li Hui; Zhang Guangxia; Wang Junwei; (21 pag.)CN109748923; (2019); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Related Products of 1520-70-3,Some common heterocyclic compound, 1520-70-3, name is Ethanesulfonamide, molecular formula is C2H7NO2S, 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 solution of free acid (50 mg, 0.11 mmol) from Example 226 in 1 ML of methylene chloride was added ethyl sulfonamide (18 mg, 0.17 mmol), EDAC (25 mg, 0.13 mmol), and DAMP (2.7 mg, 0.022 mmol) sequentially.The mixture was stirred at ambient temperature for 16 h.The solvent was then removed on a rotavap under reduced pressure and the residue was purified on an Alltech sep-pak, eluding with 1percent MeOH in EtOAc to give 30 mg (50percent yield) of the title compound as a light yellow solid. 1H NMR (CDCl3, 300 MHz) delta 1.18 (d, J=6.3 Hz, 6H), 1.34 (t, J=7.5 Hz, 3H), 1.61-1.74 (m, 2H), 1.84-2.04 (m, 1H), 2.13-2.35 (m, 1H), 2.60-2.75 (m, 2H), 3.44 (p, J=7.5 Hz, 2H), 3.53-3.66 (m, 1H), 3.66-3.85 (m, 2H), 4.00-4.18 (m, 1H), 6.71 (d, J=8.7 Hz, 1H), 6.88 (d, J=15.6 Hz, 1H), 7.31 (dd, J=2.4, 8.4 Hz, 1H), 7.41 (d, J=1.8, 8.4 Hz, 1H), 7.51 (d, J=1.8 Hz, 1H), 7.54 (d, J=8.4 Hz, 1H), 7.67 (d, J=15.6 Hz, 1H), 8.43 (s, 1H). MS (ESI+) (M+H)+ at m/z 546.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Ethanesulfonamide, its application will become more common.

Reference:
Patent; Abbott Laboratories; US2004/116518; (2004); 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. 121492-06-6, name is N-Boc-(2-Aminoethyl)-N-methylamine, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C8H18N2O2

Reference Example 61Synthesis of tert-butyl methyl-[2-(2-nitrobenzenesulfonylamino) ethyl]carbamate2-Nitrobenzenesulfonyl chloride (4.9 g, 22 mmol) was added to a dichloromethane solution (100 ml) of tert-butyl (2-aminoethyl)methyl carbamate (3.5 g, 20mmol) and triethylamine (3.3ml, 24 mmol) at 0C, and stirred at room temperature overnight. Waterwas added to the reaction mixture, and extraction with dichloromethanewas performed. The organic layer was dried over anhydrous sodiumsulfate, and concentrated under reduced pressure. The residue waspurified by silica gel column chromatography (n-hexane:ethylacetate=3:2-?2:3) . The purified product was concentrated underreduced pressure to thereby obtain 5.06 g (yield: 70%) of tert-butylmethyl-[2-(2-nitrobenzenesulfonylamino)ethyl]carbamate as a yellowoil.1H-NMR (CDC13) 5ppm:1.45 (9H, s), 2.84 (3H, s), 3.26 – 3.41 (4H, m), 7.68-7.79 (2H, m),7.79-7.90 (1H, m), 8.09-8.19 (1H, m) .

According to the analysis of related databases, 121492-06-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; OTSUKA PHARMACEUTICAL CO., LTD.; WO2009/104819; (2009); 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. 7700-07-4, name is N,N-Dimethylethenesulfonamide, A new synthetic method of this compound is introduced below., COA of Formula: C4H9NO2S

To a solution of Example 1.18.18 (69.8 mg) in N,N-dimethylformamide (6 mL) was added N,N-dimethylethenesulfonamide (118 mg), N,N-diisopropylethylamine (0.2 mL) and H20 (0.2 mL). The mixture was stirred at room temperature 4 days. The reaction mixture was diluted with ethyl acetate (200 mL), washed with water and brine, and dried over anhydrous sodium sulfate. After evaporation of the solvent, the residue was dissolved in dichloromethane and trifluoroacetic acid (10 mL, 1 :1), and the resulting solution was stirred overnight. The solvents were removed under reduced pressure. The residue was diluted with N,N-dimethylformamide (2 mL), filtered and purified by reverse-phase HPLC on a Gilson system (CI 8 column), eluting with 20-80% acetonitrile in water containing 0.1% trifluoroacetic acid, to give the title compound. NMR (400 MHz, dimethyl sulfoxide-^) delta ppm 12.82 (s, 1H), 8.53 (s, 2H), 8.00 (dd, 1H), 7.76 (d, 1H), 7.59 (dd, 1H), 7.53 – 7.37 (m, 4H), 7.37 – 7.28 (m, 2H), 7.26 (s, 1H), 6.92 (d, 1H), 4.92 (s, 2H), 3.80 (s, 2H), 3.54 (t, 2H), 3.44 – 3.34 (m, 2H), 3.30 (s, 2H), 3.11 (s, 2H), 2.98 (t, 2H), 2.77 (s, 6H), 2.07 (s, 3H), 1.39 (s, 2H), 1.27 (q, 4H), 1.11 (s, 4H), 1.06 – 0.93 (m, 2H), 0.83 (s, 7H). MS (ESI) m/e 881.2 (M+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; ABBVIE INC.; BENATUIL, Lorenzo; BRUNCKO, Milan; JUDD, Andrew, S.; LI, Yingchun; MCCLUSKEY, Andrew; PHILLIPS, Andrew, C.; PHILLIPS, Darren, C.; SEAGAL, Jane; SOUERS, Andrew, J.; (608 pag.)WO2017/214458; (2017); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

337463-88-4, name is 6-Bromo-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one, 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: C7H5BrN2O2

To a stirred solution of lla (32 g, 0.139 mol) and 6-bromo-2H-pyrido[3,2-b][l,4]oxazin- 3(4H)-one (WO2017199265, 31.7 g, 0.139 mol) in dry l,4-dioxane (50 mL), were added t-butyl-X-Phos mesyl chloride complex( 5.5 g, 0.0069 mol) and sodium tert-butoxide (19.94 g, 0.207 mol) and was degassed for 20 mins. Then, it was heated in sealed tube at 100 C for 16 h. After completion of the reaction, reaction mixture was concentrated under reduced pressure. It was purified by column chromatography on silica gel (230-400 mesh, 25-30% ethyl acetate in pet ether) to afford lib (45.6 g, 86%). LC_MS Calculated for C17H25N3O5S1, 379.49, Observed 380.0. lH NMR (400 MHz, DMSO-d6). d 7.60 (d, J = 8.68 Hz, 1H), 7.43 (d, J = 8.68 Hz, 1H), 4.77-4.73 (m, 1H), 4.67 (s, 2H), 4.15-4.10 (m, 1H), 3.93-3.89 (m, 3H), 0.79 (s, 9H), 0.04 (s, 6H).

The synthetic route of 337463-88-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BUGWORKS RESEARCH INDIA PVT LTD; PEER MOHAMED, Shahul Hameed; BHARATHAM, Nagakumar; KATAGIHALLIMATH, Nainesh; SHARMA, Sreevalli; NANDISHAIAH, Radha; RAMACHANDRAN, Vasanthi; (116 pag.)WO2019/186590; (2019); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 205318-52-1,Some common heterocyclic compound, 205318-52-1, name is 3-(Aminomethyl)-1-N-Boc-aniline, molecular formula is C12H18N2O2, 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.

3-t-Butoxycarbonylamino-benzyl-ammonium chloride (103.5 mg, 0.4 mmol) was dissolved in 1 rnL DMF in a reaction vial, and Si-dimethylamine (350 mg, 0.525 mmol) was added. The resulting mixture was agitated for 1 h, after which time/?- cyanophenylisocyanate (52 mg, 0.36 mmol) was added and the reaction mixture was agitated 8 h. SCX (113 mg, 0.1 mmol) was added and the mixture was agitated an additional 30 minutes. The reaction mixture was filtered, the flrate was concentrated, and the residue was dissolved in 5 mL dichloromethane. TFA (1 mL) was added and the mixture was stirred at room temperature for 1.5 hours. The solvents were evaporated providing 96 mg of pure intermediate (l-(3-amino-benzyl)-3-(4-cyano-phenyl)-urea) which was used directly. Synthesis of the second reagent was carried out by treating l,2,3,4-tetrahydro-isoquinoline-7-carboxylic acid methyl ester (139 mg, 0.727 mmol) with formaldehyde (1 mL, 37% aqueous) in formic acid (1 mL) and heating the resulting mixture for 62 h at 60 0C. The reaction mixture was evaporated to dryness, and the residue was taken up in dichloromethane and evaporated (3x). The intermediate, 2 -methyl- 1,2, 3, 4- tetrahydro-isoquinoline-7-carboxylic acid methyl ester, was then dissolved in methanol (2 mL) and treated with Amberlyst A26 (OH” form) (polymer-supported hydroxide exchange resin; 2240 mg, 3 mmol), and the resulting mixture was agitated overnight, then heated in the microwave at 130 0C for 40 min. After cooling to room temperature, the resin was then filtered and washed with 1 x 2 mL DMF and 3 x 2 mL methanol. The product acid was eluted with a solution of 20% formic acid in methanol (3×2 mL). The eluant solvents were evaporated to provide the pure acid (2 -methyl- 1,2,3, 4-tetrahydro- isoquinoline-7-carboxylic acid) as a formate salt (110 mg, 66% – 2 steps). Coupling of the two reagents prepared above proceeded by dissolution of the acid (86 mg, 0.45 mmol), EDC (143.8 mg, 0.75 mmol), and HOBt (74 mg, 0.55 mmol) in DMF (1 mL). Subsequently N-methylmorpholine (0.1 mL, 0.9 mmol) was added and the resulting reaction mixture was agitated for 30 min. The urea (l-(3-amino-benzyl)-3-(4-cyano- phenyl)-urea) (110 mg, 0.413 mmol) was added and the resulting mixture was agitated for 48 h. The reaction mixture was purified directly by preparative HPLC using an acetonitrile/water/formic acid gradient providing the title compound as a formate salt (53 mg, 27% yield), MS analysis electrospray, 440 (M+H).

The synthetic route of 205318-52-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BOEHRINGER INGELHEIM PHARMA GMBH & CO. KG; WO2008/86047; (2008); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 1118-69-0, name is N-Isopropylacetamide, 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 1118-69-0, Formula: C5H11NO

Preparation example 5: Preparation of (Z)-N’-(4-bromo-2,6-difluorophenyl)-N-isopropyl acetamidine 4-bromo-2,6-difluroaniline (7.87 g, 37.9 mmol)), N-isopropylacetamide (7.65 g, 75.7 mmol) and triethylamine (5.7 g, 56.9 mmol) were dissolved in toluene (150 mL), and phosphorus oxychloride (5.8 g, 37.9 mmol) was added slowly. After the addition, the mixture was heated to reflux for 3 h. Then, the reaction mixture was cooled to room temperature, the solvent was removed by reduced pressure distillation, and dichloromethane (200 mL) was added. The resultant mixture was washed with saturated sodium hydrogen carbonate solution (2×100 mL) twice, dried by anhydrous sodium sulfate, filtrated under suction, and distilled under reduced pressure, to get the solid title compound (7.3 g, yield: 66.2%).

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; Xuanzhu Pharma Co., Ltd.; WU, Frank; CHEN, Bo; (105 pag.)EP3091008; (2016); 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. 1237535-78-2, name is 5-Fluoro-3,4-dihydro-1,8-naphthyridin-2(1H)-one, This compound has unique chemical properties. The synthetic route is as follows., name: 5-Fluoro-3,4-dihydro-1,8-naphthyridin-2(1H)-one

To the mixture of the product of Step G (66.3 g, 0.3 mol) and 5-fluoro-3,4-dihydro- 1,8- naphthyridin-2(lH)-one (50 g, 0.3 mol) in DMF (850 mL) was added Potassium tert-butoxide (35.4 g, 0.32 mol) and the mixture was stirred at 120 C under nitrogen for 2hrs. The reaction was cooled to room temperature and filtered through a celite pad and the filtrate was removed half of the solvent. The residue was added into stirred 2L water in drops. A solid was precipitated out of the solution. The solid was filtered, washed with water and dried in air. The dried title compound (108.2 g, 98%) as a gray solid was used into next step directly. XH NMR (400 MHz, DMSO-^6) delta 10.43 (s, 1H), 7.92 (d, J= 5.8 Hz, 1H), 7.30 (d, J= 2.4 Hz, 1H), 6.98 (d, J= 8.8 Hz, 1H), 6.94 (dd, J= 8.8, 2.4 Hz, 1H), 6.21 (d, J= 5.8 Hz, 1H), 5.26 (dd, J= 5.4, 1.0 Hz, 1H), 4.08 (q, J= 7.0 Hz, 2H), 3.34 (dd, J= 5.4, 3.2 Hz, 1H), 2.89 (t, J= 7.8 Hz, 2H), 2.51 (t, J= 7.8 Hz, 2H), 1.34 (dd, J= 3.2, 1.0 Hz, 1H), 1.18 (t, J= 7.0 Hz, 3H) ppm. MS: M/e 367 (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 1237535-78-2.

Reference:
Patent; BEIGENE, LTD.; ZHOU, Changyou; ZHANG, Guoliang; WO2014/206344; (2014); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 177906-48-8, 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. 177906-48-8, name is trans-N-Boc-1,4-cyclohexanediamine belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Reaction of 8 with tert-butyl trans-4-aminocyclohexylcarbamate, as for the synthesis of 62a, gave tert-butyl trans-4-{[4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-1,3,5-triazin-2-yl]amino}cyclohexylcarbamate (85a) in 88% yield: mp (CH2Cl2/hexanes) 218-221 C; 1H NMR (DMSO-d6) delta 8.10 and 7.97 (2d, J = 8.3, 8.1 Hz, 1H), 7.87 and 7.72 (2t, JHF = 53.1, 53.0 Hz, 1H) 7.83 and 7.77 (2d, J = 7.7, 8.10 Hz, 1H), 7.38 (q, J = 8.3 Hz, 1H), 6.94 (t, J = 8.0 Hz, 1H), 6.75-6.70 (m, 1H), 3.98 and 3.97 (2s, 3H), 3.97 (m, 4H), 3.71-3.69 (m, 4H), 1.98-1.91 (m, 2H), 1.85-1.82 (m, 2H), 1.40-1.22 (m, 4H), 1.38 (s, 9H); Anal. Calcd. for C27H36F2N8O4: C, 56.4; H, 6.3; N, 19.5; Found: C, 56.6; H, 6.5; N, 19.3%.

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, trans-N-Boc-1,4-cyclohexanediamine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Gamage, Swarna A.; Giddens, Anna C.; Tsang, Kit Y.; Flanagan, Jack U.; Kendall, Jackie D.; Lee, Woo-Jeong; Baguley, Bruce C.; Buchanan, Christina M.; Jamieson, Stephen M.F.; Shepherd, Peter R.; Denny, William A.; Rewcastle, Gordon W.; Bioorganic and Medicinal Chemistry; vol. 25; 20; (2017); p. 5859 – 5874;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics