Month: December 2020

Adding a certain compound to certain chemical reactions, such as: 6083-47-2, name is 4-(Dimethylamino)benzamide, 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 6083-47-2, 6083-47-2

General procedure: A 12 mL vial was charged with Pd(OAc)2 (2 mol%), BuPAd2 (6 mol%), and a stirring bar. Then, 2 ml dioxane and 1 mmol of bromobenzene were injected by syringe. The vial (or several vials) was placed in an alloy plate, which was transferred into a 300 mL autoclave of the 4560 series from Parr Instruments under argon atmosphere. After flushing the autoclave three times with NH3, a pressure of 2 bar NH3 and 2 bar CO was adjusted at ambient temperature. Then, the reaction was performed for 16 hours at 100 oC. After the reaction is finished, the autoclave was cooled down to room temperature and the pressure was released carefully. Then, CuI (5 mol%), DMEDA (10%), K2CO3 (3 mmol) and 1,2-dibromobenzene were added in under air, the vial was closed and heated to 110oC for 20 hours. The reaction mixture cooled down to room temperature. The solution was extracted 3-5 times with 2-3 ml of ethyl acetate from aqua solution. After evaporation of the organic solvent the residue was adsorbed on silica gel and the crude product was purified by column chromatography using n-heptane/AcOEt (20:1) as eluent.

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, 4-(Dimethylamino)benzamide, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Wu, Xiao-Feng; Neumann, Helfried; Neumann, Stephan; Beller, Matthias; Tetrahedron Letters; vol. 54; 24; (2013); p. 3040 – 3042;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Some common heterocyclic compound, 142-26-7, name is N-Acetylethanolamine, molecular formula is C4H9NO2, 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. 142-26-7

To a solution of 3-((4-carbamoyl-2,6-difluorophenoxy)methyl)-4-chlorobenzo[ib]thiophene-2- carboxylic acid 69 (150 mg, 0.38 mmol) in DMF (8 ml.) was added N-( 2- hydroxyethyl)acetamide (78 mg, 0.76 mmol), EDCI -HCI (146 mg, 0.76 mmol) and DMAP (10 mg, 0.076 mmol) and the mixture was stirred at room temperature for 4 h. Water (150 ml.) was added and the mixture was extracted with EtOAc (100 ml. x 3). The combined organic extracts were washed with water (3 x 150 ml_), brine, dried over Na2S04, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography (DCM/MeOH = 1 :0 to 100:1 ) to give the title compound (60 mg, 73%) as a white solid. LCMS-C: rt 2.22 min; m/z 482.9 [M+H]+, 504.9 [M+Na]+. 1H NMR (400 MHz, DMSO-de) d 8.14 (dd, J = 7.9, 1.2 Hz, 1 H), 8.06 – 8.00 (m, 2H), 7.66 – 7.53 (m, 5H), 6.13 (s, 2H), 4.22 (t, J = 5.6 Hz, 2H), 3.35 (t, J = 5.6 Hz, 2H), 1.80 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 142-26-7, its application will become more common.

Reference:
Patent; CTXT PTY LIMITED; MORROW, Benjamin, Joseph; CAMERINO, Michelle, Ang; WALKER, Scott, Raymond; STEVENSON, Graeme, Irvine; STUPPLE, Paul, Anthony; (266 pag.)WO2019/219820; (2019); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

125664-95-1, A common compound: 125664-95-1, name is N-Propionyl-(2R)-bornane-10,2-sultam, belongs to amides-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

A 1 M solution of NaHMDS in THF (8.3 mL, 8.3 mmol) was added over the course of 15 min to a stirred solution of (N-propionyl)-(2R)-bornane-10,2-sultam 12 (0.20 M in THF, 41.5 mL) and TBAI (0.61 g, 1.65 mmol) at -78 C. The reaction mixture was kept at this temperature for 1 h under stirring. A solution of the allyl bromide 11 (4.98 M in HMPTA, 2.2 mL) was then added dropwise to the stirring reaction mixture. The cooling bath was replaced by an octane-liquid nitrogen bath (-50 C). The reaction mixture was stirred at -50 C for 4 h and then slowly (1 h) warmed to -25 C, quenched with water (80 mL), warmed to rt and extracted with ether (4 ¡Á 50 mL). The combined organic extracts were washed with brine, dried over MgSO4 and concentrated under reduced pressure. Compound 13 (3.58 g, 77%) was isolated by column chromatography on silica gel (petroleum ether/ethyl acetate) as a colourless viscous oil; 1H NMR (CDCl3) d 0.76 (d, J = 6.7 Hz, 3H, 6-Me), 0.89 (d, J = 6.7 Hz, 1.5H, 6-Me), 0.95 (s, 3H, CH3 in bornane), 1.04 (d, J = 5.6 Hz, 1.5H, 6-Me), 1.12 (s, 1.5H, CH3 in bornane), 1.14 (s, 1.5H, CH3 in bornane), 1.17 (t, J = 5.6 Hz, 1.5H, 2-Me), 1.19 (t, J = 5.4 Hz, 1.5H, 2-Me), 1.27-2.22 (m, 14H, 3 ¡Á CH2 in bornane, CH in bornane, CH2CH2CH2 in tetrahydropyran, 6-H), 2.39-2.50 (m, 1H, 3-H), 2.68-2.77 (m, 1H, 3-H), 3.31- 3.52 (m, 4H, CH2S, CHN in bornane, 2-H), 3.54 (d, J = 7.4 Hz, 0.5H, 5-H), 3.66 (d, J = 8.7 Hz, 0.5H, 5-H), 3.76-3.91 (m, 2H, CH2O in tetrahydropyran), 4.51 (dd, J = 3.3, 2.8 Hz, 0.5H, OCHO in tetrahydropyran), 4.56 (dd, J = 3.3, 2.8 Hz, 0.5H, OCHO in tetrahydropyran), 4.95-4.98 (m, 0.5H, C=CH2), 4.99-5.01 (m, 0.5H, C=CH2), 5.00-5.04 (m, 0.5H, C=CH2), 5.12-5.16 (m, 0.5H, C=CH2); 13C NMR (CDCl3) d 16.7, 17.2, 18.3, 19.1, 19.3, 19.4, 19.8, 19.9, 20.6 (¡Á 2), 20.8, 25.4, 25.5, 26.4, 28.8, 30.1 30.5, 30.8, 31.0, 32.8, 32.9, 35.1, 36.6, 37.1, 37.2, 38.4 (¡Á 2), 44.5, 44.6, 47.7 ( 2), 48.2, 48.4, 52.9, 53.1, 62.0, 62.9, 65.1, 65.4 ( 2), 84.7, 87.2, 94.4, 100.1, 112.4, 114.3, 144.4, 146.1, 172.6, 175.8; IR (CCl4) numax: 3086, 1701, 1649 cm-1. Anal. Calcd for C25H41NO5S: C, 64.21; H, 8.84. Found: C, 64.17; H, 8.76.

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, N-Propionyl-(2R)-bornane-10,2-sultam, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Shklyaruck, Denis; Matiushenkov, Evgenii; Tetrahedron Asymmetry; vol. 22; 13; (2011); p. 1448 – 1454;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

25408-61-1, A common heterocyclic compound, 25408-61-1, name is 2,2-Dimethoxy-N,N-dimethylacetamide, molecular formula is C6H13NO3, 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.

[0184] Combine 1-methyl-2-nitro-4-trifluoromethoxybenzene (3.73 g, 16.86 mmol), pyrrolidine (1.32 g, 18.55 mmol),N,N-dimethylformamide dimethyl acetal (6.03 g, 50.58 mmol), and dry DMF (35 ml). Heat to about 105. After 19 hours,remove the DMF under reduced pressure to give an oily residue. Combine the residue and ethyl acetate, wash withbrine, dry (Na2SO4), then concentrate to give N,N-dimethyl-2-(2-nitro-4-trifluoromethoxyphenyl)vinylamine.

The synthetic route of 25408-61-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ELI LILLY AND COMPANY; Chen, Zhaogen; Cohen, Michael Philip; Fisher, Matthew Joseph; Gillig, James Ronald; McCowan, Jefferson Ray; Miller, Shawn Christopher; Schaus, John Mehnert; Giethlen, Bruno; (141 pag.)EP1859798; (2015); B1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

63920-73-0, These common heterocyclic compound, 63920-73-0, name is 2-Amino-4,6-dimethoxybenzamide, 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 solution of 2-amino-4,6-dimethoxy-benzamide (0.19 g, 0.98 mmol) in N,N-dimethylacetamide (4 mL) were added 4-(2,5-dioxo-imidazolidin-1-ylmethyl)-benzaldehyde (0.19 g, 0.89 mmol), sodium hydrogen sulfite (58.5 wt %, 0.24 g, 1.30 mmol) and p-toluenesulfonic acid monohydrate (34 mg, 0.18 mmol) and the reaction mixture was stirred at 115 C. for 17 hours under nitrogen, then cooled to room temperature. The precipitate was filtered, washed with methanol, water, then methanol, and dried in air. The solid was suspended in hot DMSO (approximately 3 mL); saturated aqueous NaHCO3 (approximately 3 mL) and water were added. The solid was filtered, washed with water, then methanol, and air dried to give the title compound as a light yellow solid. Yield: 0.16 g (46%). MP 317-318 C. 1H NMR (400 MHz, DMSO-d6): delta 12.05 (s, 1H), 8.17 (s, 1H), 8.12 (d, J=8.4 Hz, 2H), 7.40 (d, J=8.4 Hz, 2H), 6.74 (d, J=2.0 Hz, 1H), 6.54 (d, J=2.0 Hz, 1H), 4.61 (s, 2H), 4.02 (s, 2H), 3.89 (s, 3H), 3.85 (s, 3H). MS (ES+) m/z: 395.09 (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 63920-73-0.

Reference:
Patent; Resverlogix Corp.; Hansen, Henrik C.; (96 pag.)US9238640; (2016); B2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Some common heterocyclic compound, 85006-25-3, name is tert-Butyl (tert-butoxycarbonyl)oxycarbamate, molecular formula is C10H19NO5, 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. 85006-25-3

Scheme 1: Reagent and conditions; (a) tert-butyl(tert-butoxycarbonyl)oxycarbamate, iN NaOH, TBAB, DCM; (b) TFA, DCM; (c) 3,3-difluoro-2,2-dimethylbutanoic acid, EDCI, DIEA, DMF, rt, 12h(d) NaH, Mel, THF.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 85006-25-3, its application will become more common.

Reference:
Patent; NATIONAL INSTITUTE OF BIOLOGICAL SCIENCES, BEIJING; ZHANG, Zhiyuan; WANG, Xiaodong; LEI, Xiaoguang; SU, Yaning; HE, Sudan; RUAN, Hanying; SUN, Liming; (103 pag.)WO2016/101885; (2016); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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 53250-82-1 as follows. 53250-82-1

General procedure: To a stirred solution of 11 (13.14 mmol) in 1,2-dichloroethane (240 mL) were added appropriate substituted anilines (19.71 mmol) and AcOH (13.14 mmol), and the mixture was heated to reflux for 2 h under nitrogen atmosphere. The reaction mixture was cooled to 0 C, and MeOH (60 mL) and THF (20 mL) were added. To it, (AcO)3BHNa (26.20 mmol) or NaBH4 (52.56 mmol) was added portionwise, and then the reaction mixture was allowed to warm to room temperature and stirred for an additional 3 h. The pH of the reaction mixture was adjusted to 7-8 at 0 C with 1 NHCl, and then the organic layer was separated. The aqueous layer was extracted with CH2Cl2 (2¡Á 300 mL). The combined organic layers was washed with brine (300 mL) and dried over anhydrous Na2SO4, filtered, and evaporated to dryness under reduced pressure. The residue was purified by MPLC on silica gel to afford the titled compounds as a solid.

According to the analysis of related databases, 53250-82-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Jin, Cheng Hua; Krishnaiah, Maddeboina; Sreenu, Domalapally; Subrahmanyam, Vura Bala; Park, Hyun-Ju; Park, So-Jung; Sheen, Yhun Yhong; Kim, Dae-Kee; Bioorganic and Medicinal Chemistry; vol. 22; 9; (2014); p. 2724 – 2732;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

847361-67-5, 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. 847361-67-5, name is 1-(4-Bromophenyl)cyclopropanecarboxamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A solution of the bromide from Step 4 (1.0 g, 4.16 mmol), commercially available 4-(dihydroxyboranyl)benzoic acid (0.73 g, 4.37 mmol), sodium carbonate (2 M aq. solution, 5.2 mL, 10.4 mmol), tetrakis(triphenylphosphine)palladium(0) (20 mg, 0.017 mmol) in water (8 mL) and acetontrile (12 mL) was heated to 60C and stirred overnight. The reaction mixture was cooled, filter and the mother liquors were concentrated. The residual aqueous mixture was acidified with 1 N HCl. The resultant milky suspension was filtered to provide a pale grey solid which was further dried under high vacuum to provide the title compound (1.1 g).

The synthetic route of 1-(4-Bromophenyl)cyclopropanecarboxamide has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK FROSST CANADA LTD.; BLACK, Cameron; BEAULIEU, Christian; WO2010/148488; (2010); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

69065-91-4, These common heterocyclic compound, 69065-91-4, name is Ethyl 2-((4-fluorophenyl)amino)-2-oxoacetate, 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: A mixture of 1.1 g (5 mmol) of amine 1 and 5 mmol of anilido ester 6a-6f was heated for 5 h at 120-125C. The resulting solid was treated with hexane, and the precipitate was filtered off, washed with water, 10% aqueous HCl, and water again, dried in air, and recrystallized from ethanol.

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 69065-91-4.

Reference:
Article; Aghekyan; Mkryan; Muradyan; Tumajyan; Russian Journal of Organic Chemistry; vol. 54; 6; (2018); p. 886 – 891; Zh. Org. Khim.; vol. 54; 6; (2018); p. 884 – 889,6;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding some certain compound to certain chemical reactions, such as: 150349-36-3, name is 3-(N-Boc-N-methylamino)propylamine, 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 150349-36-3. 150349-36-3

24? was synthesized on 2-chlorotrityl resin using standard Fmoc chemistry by loading 1.1 mmol Fmoc glycine on resin, and subsequent coupling of Fmoc leucine, Fmoc phenylalanine, Fmoc glycine, and 6-maleimidohexanoic acid. Resin cleavage by addition of TFA, and trituration with MTBE, provided crude 24?. This was dissolved in DMF (5 mL), and N,N?-diisopropylcarbodiimide (277 mg, 2.20 mmol), HOBt (297 mg, 2.20 mmol) and diisopropylethylamine (0.5 mL) were added. The reaction was stirred at room temperature for 3 h, and purification by preparative HPLC (water with 0.05% TFA/acetonitrile) provided 25? (249 mg, 0.329 mmol, 30% yield). LCMS M/Z = 756.4 [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 3-(N-Boc-N-methylamino)propylamine.

Reference:
Patent; TARVEDA THERAPEUTICS, INC.; BILODEAU, Mark T.; SIMCOX, Mary; WHITE, Brian H.; KADIYALA, Sudhakar; WOOSTER, Richard; (178 pag.)WO2017/180834; (2017); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics