Month: February 2021

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

Adding a certain compound to certain chemical reactions, such as: 72594-62-8, name is tert-Butyl naphthalen-1-ylcarbamate, 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 72594-62-8, Product Details of 72594-62-8

General procedure: Under argon, to a solution of N-Boc-1-naphthylamine (1a) or 1-naphthyl-N-pivalamide (1b) (2.2 mmol) in dry Et2O (15 mL) at -20 C, t-BuLi in pentane (4.6 mmol) was added dropwise. The reaction mixture was stirred at this temperature for 2 h. Next, to the solution of lithiated species was added dropwise at -20 C, a solution of an appropriate electrophile (ethyl chloroformate, 2.2 mmol) in dry Et2O (10 mL). Then, the mixture was allowed to warm to room temperature and was stirred under these conditions for 2 h. After this time, to the reaction mixture a saturated solution of NH4Cl (20 mL) was added and was stirred for 0.5 h. The water layer was separated and extracted subsequently with Et2O (3¡Á20 mL). The organic phase was dried over MgSO4 and concentrated till dryness. The crude material was separated by flash chromatography.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, tert-Butyl naphthalen-1-ylcarbamate, and friends who are interested can also refer to it.

Reference:
Article; Nowak, Monika; Malinowski, Zbigniew; Jo?wiak, Andrzej; Fornal, Emilia; B?aszczyk, Alina; Kontek, Renata; Tetrahedron; vol. 70; 34; (2014); p. 5153 – 5160;,
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. 193751-54-1, name is tert-Butyl cyclopent-3-en-1-ylcarbamate, A new synthetic method of this compound is introduced below., category: amides-buliding-blocks

(0243) To a stirred suspension of LiAlH4 (3.74 g, 0.09852 mol) in 200 ml anhydrous THF in a two neck RBF (1 L), was added a solution of 514 (10 g, 0.04926 mol) in 70 mL of THF slowly at 0 C. under nitrogen atmosphere. After complete addition, reaction mixture was warmed to room temperature and then heated to reflux for 4 h. Progress of the reaction was monitored by TLC. After completion of reaction (by TLC) the mixture was cooled to 0 C. and quenched with careful addition of saturated Na2SO4 solution. Reaction mixture was stirred for 4 h at room temperature and filtered off. Residue was washed well with THF. The filtrate and washings were mixed and diluted with 400 mL dioxane and 26 mL conc. HCl and stirred for 20 minutes at room temperature. The volatilities were stripped off under vacuum to furnish the hydrochloride salt of 515 as a white solid. Yield: 7.12 g 1H-NMR (DMSO, 400 MHz): delta=9.34 (broad, 2H), 5.68 (s, 2H), 3.74 (m, 1H), 2.66-2.60 (m, 2H), 2.50-2.45 (m, 5H). (0244) Synthesis of 516:

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; Alnylam Pharmaceuticals, Inc.; Novobrantseva, Tatiana; Bettencourt, Brian; Milstein, Stuart; Borodovsky, Anna; US9127275; (2015); B2;,
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. 85006-25-3, name is tert-Butyl (tert-butoxycarbonyl)oxycarbamate, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 85006-25-3

Reagent and conditions: (a) tert-butyl (tert-butoxycarbonyl) oxycarbamate, 1N NaOH, TBAB, DCM; (b) TFA, DCM; (c) 2, 2-dimethylbutanoyl chloride, aq. NaHCO 3, THF, H 2O. Tert-butyl (tert-butoxycarbonyl) oxycarbamate (400 mg) and 1- (bromomethyl-d2) benzene-2, 3, 4, 5, 6-d5 (100mg) were dissolved in CH 2Cl 2 (4 ml) . The mixture was added 1M NaOH (2 ml) and tetrabutylammonium bromide (25.2 mg) , and stirred at room temperature for overnight. The resulting mixture was washed with water and dried with Na 2SO 4, concentrated in vacuo and purification by silica gel chromatography to give tert-butyl ( (tert-butoxycarbonyl) oxy) ( (phenyl- d5) methyl-d2) carbamate (510 mg, 99%) . 1HNMR (400 MHz, CDCl 3) delta 1.46 (s, 9H) , 1.44 (s, 9H) .

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 85006-25-3.

Reference:
Patent; SU, Yaning; SIRONAX LTD; ZHANG, Zhiyuan; YANG, Yi; WANG, Guozheng; LIU, Wendong; MA, Yongfen; REN, Yan; (74 pag.)WO2020/103859; (2020); 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. 16695-22-0, name is (Tosylazanediyl)bis(ethane-2,1-diyl) bis(4-methylbenzenesulfonate), A new synthetic method of this compound is introduced below., Quality Control of (Tosylazanediyl)bis(ethane-2,1-diyl) bis(4-methylbenzenesulfonate)

Synthesis of Intermediate XVI. To a solution of Tritosylate XV (1 g, 0.00176 moles, 1 eq) in 6 ml of DMF was added NaBr (0.93 g, 0.009 moles, 5 eq). The resulting suspension was stirred in an oil bath at 120 C. for 4 h. After cooling to room temperature, the reaction mixture was concentrated to about 2 ml. The viscous milky product was poured into rapidly stirred mixture of ice-water (30 ml) and extracted with ethyl acetate (30 ml). The organic phase was dried (Na2SO4) and concentrated under reduced pressure. The crude product was purified by column chromatography (silica gel, 60-120 mess, 10% ethyl acetate in hexane) to leave the product XVI as a pale yellow liquid (0.34 g, 51%) 1H NMR (400 MHz, CDCl3) 2.41 (s, 3H), 3.44 (s, 8H), 7.38 (d, 4H), 7.76 (d, 4H)

The synthetic route of 16695-22-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Salituro, Francesco G.; Saunders, Jeffrey; Yan, Shunqi; US2012/172349; (2012); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 18807-71-1, 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. 18807-71-1, name is Benzyl N-(2-aminoethyl)carbamate hydrochloride belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 178; 4-[7-(2-Oxo-imidazolidin-1-yl)-quinazolin-4-yl]-piperidine-1-carboxylic acid (4-pyrrolidin-1-yl-phenyl)-amide; a. 4-[7-(2-Oxo-imidazolidin-1-yl)-quinazolin-4-yl]-piperidine-1-carboxylic acid tert-butyl ester; To a mixture of 4-(7-fluoro-quinazolin-4-yl)-piperidine-1-carboxylic acid tert-butyl ester (458 mg, 1.38 mmol), which was prepared as described in Example 65b, and (2-amino-ethyl)-carbamic acid benzyl ester hydrochloride (446 mg, 1.93 mmol) in DMSO (1.0 mL) was added K2CO3 (1.52 g, 11.04 mmol). The mixture was stirred at 115 C. overnight and subsequently partitioned between EtOAc and water. The combined organic extracts were washed with brine, dried over Na2SO4 and evaporated. The residue was purified by flash column chromatography on silica gel (EtOAc as eluent) to afford the desired product as a white solid (400 mg, 73%). 1H NMR (CDCl3) delta 9.13 (s, 1H), 8.69 (dd, J=9.40 and 2.35 Hz, 1H), 8.08 (d, J=9.53 Hz, 1H), 7.42 (d, J=2.33 Hz, 1H), 5.25 (br, 1H), 4.31 (m, 2H), 4.09 (t, J=8.21 Hz, 2H), 3.69 (t, J=8.14 Hz, 2H), 3.63 (m, 1H), 2.95 (m, 2H), 1.77-2.04 (4H), 1.48 (s, 9H). Calcd for C21H28N5O3 (MH+) 398.3, found 398.3.

The synthetic route of Benzyl N-(2-aminoethyl)carbamate hydrochloride has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Baindur, Nand; Gaul, Michael David; Kreutter, Kevin Douglas; Baumann, Christian Andrew; Kim, Alexander J.; Xu, Guozhang; Tuman, Robert W.; Johnson, Dana L.; US2006/281772; (2006); 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. 1103234-56-5, name is 2,6-Difluoro-3-(propylsulfonamido)benzoic acid, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 2,6-Difluoro-3-(propylsulfonamido)benzoic acid

Example GN-(3 -Amino-2,4-difluorophenyl)propane- 1 -sulfonamideTo a solution of 2,6-difluoro-3-(propylsulfonamido)benzoic acid (4.078 g, 14.6 mmol) inTHF (60 mL) was added triethylamine (4.68 mL, 33.59 mmol) and diphenylphosphonic azide (3.73 mL, 16.79 mmol). The reaction mixture was stirred at room temperature for 3 hours and then warmed to 80 0C for 2 hours. Water (10 mL) was added, and the mixture stirred at 80 0C for 15 hours. The reaction mixture was diluted with 300 mL of EtOAc, and the organic layer was washed with saturated aq. NaHCO3 solution and brine. The solvent was removed under reduced pressure and the residual purified via silica gel column chromatography eluting with 30/70 EtOAc/hexane to obtain 2.03 g (55%) of the title compound. 1H NMR (400 MHz, DMSO- d6) delta 9.32 (s, IH), 6.90-6.80 (m, IH), 6.51 (td, J=8.7, 5.5 Hz, IH), 5.28 (s, 2H), 3.05-2.96 (m, 2H), 1.82-1.64 (m, 2H), 1.01-0.90 (m, 3H). LC/MS: m/z 251.1 [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 1103234-56-5.

Reference:
Patent; ARRAY BIOPHARMA INC.; GENENTECH, INC.; ALIAGAS, Ignacio; GRADL, Stefan; GUNZNER, Janet; LEE, Wendy; MATHIEU, Simon; RUDOLPH, Joachim; WEN, Zhaoyang; ZHAO, Guiling; BUCKMELTER, Alexandre J.; GRINA, Jonas; HANSEN, Joshua D.; LAIRD, Ellen; MORENO, David; REN, Li; WENGLOWSKY, Steven Mark; WO2011/25938; (2011); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics