Tag: M.W=100-200

5466-88-6, 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. 5466-88-6 name is 2H-1,4-Benzoxazin-3(4H)-one, 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.

2. Synthesis of 3-oxo-3,4-dihydro-2H-benzo[b’||’l,4]oxazine-6-sulfonyl chloride.2H-Benzo[b][l,4]oxazin-3(4H)-one (13.4 mmol) was added in several batches over 20 min to sulfurochloridic acid (10 mL) at 0 0C and the reaction mixture was maintained for 1 h. The reaction mixture was cautiously poured into ice (100 g) and the resulting mixture was extracted with dichloromethane (100 mL). The organic layer was dried (sodium sulfate) and concentrated to provide 3-oxo-3,4-dihydro-2H-benzo[b][l,4]oxazine-6-sulfonyl chloride in 66% yield as a white solid. Data: 1HNMR (400MHz, CDC13) delta 9.29 (s, IH), 7.71 (d, 2H), 7.52 (s, IH), 7.16 (d, 2H), 4.80 (s, 2H). LC/MS (ES) m/z 317 [M+BnNH-H].

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2H-1,4-Benzoxazin-3(4H)-one, and friends who are interested can also refer to it.

Reference:
Patent; MEMORY PHARMACEUTICALS CORPORATION; DANCA, Mihaela, Diana; DUNN, Robert; TEHIM, Ashok; XIE, Wenge; WO2010/21797; (2010); A1;,
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5466-88-6, 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. 5466-88-6, name is 2H-1,4-Benzoxazin-3(4H)-one, This compound has unique chemical properties. The synthetic route is as follows.

To a stirred solution of 4H-Benzo[1,4]oxazin-3-one (2.5 g, 16.77 mmol) in DMF (10 mL) was added potassium tert-butoxide (2.81 g, 25.16 mmol) at 0 C. After stirring for 5 min, methyl iodide (3.54 g, 25.16 mmol) was added and the reaction mixture was stirred for another 3 h. The reaction was quenched by addition of water and extracted with ethyl acetate (30¡Á2 ml). The organic layer was washed with water (20 mL), and evaporated to get a crude product 2.2 g.

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; NOVARTIS AG; US2012/196813; (2012); A1;,
Amide – Wikipedia,
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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;,
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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;,
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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

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;,
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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;,
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1885-32-1, The chemical industry reduces the impact on the environment during synthesis 1885-32-1, name is 2-Amino-3-methylbenzamide, I believe this compound will play a more active role in future production and life.

Preparation 14 2-(5-Acetyl-2-ethoxybenzamido)-3-methylbenzamide Oxalyl chloride (3.66 g, 0.0288 mol) was added dropwise to a stirred solution of 5-acetyl-2-ethoxy-benzoic acid (3 g, 0.00144 mol) and dimethylformamide (0.1 ml) in dichloromethane (15 ml). The mixture was stirred at room temperature for 3 hours, then the solvent evaporated under vacuum and the residue azeotroped with hexane (3*50 ml). The crude acyl chloride was dissolved in dichloromethane (20 ml) and the solution added dropwise to a stirred solution of 2-amino-3-methylbenzamide (2.16 g, 0.0144 mol) in pyridine (40 ml) at 0 C. The mixture was allowed to warm to room temperature and stirred for a further 18 hours. The solvent was removed by evaporation under vacuum, the residue dissolved in dichloromethane (50 ml) and this solution then washed with saturated aqueous sodium carbonate solution (50 ml), 2N hydrochloric acid (50 ml) and brine (50 ml), then dried (Na2SO4) and evaporated under vacuum. Trituration of the residue with diethyl ether gave the title compound as a white solid (2.14 g, 44%), m.p. 214-216 C.

The chemical industry reduces the impact on the environment during synthesis 2-Amino-3-methylbenzamide. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Cell Pathways, Inc.; US6562830; (2003); B1;,
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 1015-89-0 as follows. 1015-89-0

(ii) BDS, THF, reflux, 24 h; (yield 20percent)

According to the analysis of related databases, 1015-89-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ROBERTS, Edward; MITTAPALLI, Gopi Kumar; VELLUCCI, Danielle; YANG, Jun; GUERRERO, Miguel; URBANO, Mariangela; ROSEN, Hugh; WO2014/116684; (2014); A1;,
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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. 72179-84-1 name is (Methylsulfamoyl)amine, 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. 72179-84-1

Example 67 (100 mg, 0.259 mmol) was dissolved in tetrahydrofuran (4 mL) and carbonyldiimidazole (63.1 mg, 0.389 mmol) was added. The mixture was heated to 60 C for 1 hour. More carbonyldiimidazole (63.1 mg, 0.3 89 mmol) was added, and the resultant solution was stirred at 60 C for 1 hour. The solution was cooled down to room temperature and was then added dropwise through a syringe to a solution of 1,8-diazabicyclo[5.4.0]undec-7-ene (0.117 mL 0.778 mmol, DBU) and N-methylsulfuric diamide (86 mg, 0.778 mmol) in 0.6 mL tetrahydrofuran. The resulting mixture was stirred at room temperature overnight. The mixture was acidified with 1 N HC1 to pH=6-7 and then extracted with ethyl acetate 3 times. The organic layers were combined and concentrated. The residue was diluted with methanol to give a solution which was purified by preparative HPLC (0.1% CF3CO2H in H20/CH3CN) and lyophilized to give the titled compound (72.5 mg, 0.152 mmol, 58.5% yield). ?H NMR (400 MHz, DMSO-d6) ppm 11.39 (s, 1H), 7.46 (q, J = 4.9, 4.5 Hz, 1H), 7.14 (dd, J = 56.8, 38.2 Hz, 5H), 6.50 (s, 2H), 3.74 (s, 6H), 3.67-3.58 (m, 1H), 3.46 (d, J = 19.0 Hz, 4H), 3.19 (s,1H), 2.60 (s, 3H), 2.40 (s, 2H), 1.98 (s, 3H), 1.82 (a, J = 16.8 Hz, 2H); LC-MS (ESI+) m/z 478.2 (M+H), RT = 1.9 19 minutes.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, (Methylsulfamoyl)amine, and friends who are interested can also refer to it.

Reference:
Patent; ABBVIE INC.; BLACK, Lawrence, A.; BUNNELLE, William, H.; CHEN, Da; CLAPHAM, Bruce; DEGOEY, David, A.; DENG, Xiangjun; FU, Liqiang; HAZELWOOD, Lisa, A.; KONG, Linglong; LANG, Qingyu; LEE, Chih-Hung; LI, Mingfeng; LUNDGAARD, Greta, L.; PATEL, Meena, V.; TAO, Ruihong; ZHANG, Lin; ZHANG, Qingwei; ZHENG, Qiangang; ZHU, Wei; (289 pag.)WO2017/177004; (2017); A1;,
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Amide – an overview | ScienceDirect Topics