Tag: M.W=100-200

Electric Literature of 17641-08-6, 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 17641-08-6 as follows.

General procedure: A mixture of the key intermediate 13 (1.0 mmol), diverse 2-chloro-N-sbustituted acetamidederivatives 15 (1.0 mmol) and potassium carbonate (K2CO3) (0.15 g, 1.1 mmol) in 5.0 mL ofanhydrous ethanol was stirred and refluxed for 2.0-2.5 h. After the reaction was complete accordingto the TLC detection, the precipitate was filtered off and solvent was removed under reducedpressure and the residue was purified by column chromatography to give the target compounds inyields of 57-78%.

According to the analysis of related databases, 17641-08-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Zhao, Pei-Liang; Chen, Peng; Li, Qiu; Hu, Meng-Jin; Diao, Peng-Cheng; Pan, En-Shan; You, Wen-Wei; Bioorganic and Medicinal Chemistry Letters; vol. 26; 15; (2016); p. 3679 – 3683;,
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Synthetic Route of 16982-21-1, A common heterocyclic compound, 16982-21-1, name is Ethyl 2-amino-2-thioxoacetate, molecular formula is C4H7NO2S, 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.

4B. Ethyl 4-phenylthiazole-2-carboxylate A mixture of 2-bromo-1-phenylethanone (1.790 g, 8.99 mmol) and ethyl 2-amino-2-thioxoacetate (Example 4A, 1.20 g, 9.01 mmol) in benzene (80 mL) and ethanol (10 mL) was stirred at room temperature for 18 h. The mixture was heated at 80 C. for 1 h. The solvent was evaporated under reduced pressure and the residue was partitioned between ethyl acetate (300 mL) and saturated aqueous sodium bicarbonate (100 mL). The organic phase was washed with brine, dried over anhydrous magnesium sulfate and concentrated in vacuo. The residual clear oil was chromatographed on silica gel (4*10 cm, elution toluene-ethyl acetate 0-2-4%) and gave a yellow oil (1.588 g). This was distilled in vacuo (bp: 105-115 C./0.1 torr, bulb to bulb distillation, air bath temperature) to provide the title material (1.409 g, 67%) as a pale yellow syrup which solidified to an almost colorless solid upon standing. LC (Method C): 2.009 min. HRMS (ESI) calcd for C12H12NO2S [M+H]+ m/z 234.0583. found 234.0597. 1H NMR (CDCl3, 400 MHz) delta ppm: 1.48 (t, J=7.2 Hz, 3H), 4.52 (q, J=7.2 Hz, 2H), 7.35-7.49 (m, 3H), 7.75 (s, 1H), 7.93-8.00 (m, 2H).

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; Kornacker, Michael G.; Mapelli, Claudio; Riexinger, Douglas James; US2013/289238; (2013); A1;,
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Synthetic Route of 1746-77-6,Some common heterocyclic compound, 1746-77-6, name is Isopropyl carbamate, 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.

Isopropyl carbamate (30 g, 291 mmol, available from TCI) was charged to a 3 L Lara vessel and dry Tetrahydrofuran (THF) (150 ml) added. (2E)-2-butenoyl chloride (31.2 ml, 326 mmol, available from Aldrich) was added under nitrogen and the jacket cooled to -30 C. When the solution temperature reached -17 C. 1M Lithium tert-butoxide (655 ml, 655 mmol) was added by peristaltic pump over 2 hours, keeping the reaction temperature between -10 C. and -18 C. Once the addition was complete the mixture was complete the mixture was stirred for 30 mins and brought to 0 C. Diethyl ether (450 ml) and 1M HCl (375 ml) were added and the mixture brought to 20 C. with vigorous stirring. The stirring was stopped, the layers allowed to separate and the aqueous layer run off. Brine (375 ml) was added and the mixture stirred vigorously. The stirring was stopped, the layers allowed to separate and the aqueous layer run off. The organic layer was dried (magnesium sulfate), filtered and evaporated to a brown oil (60 g). The mixture was loaded on to a 40+M Biotage silica column and eluted with DCM:ethyl acetate (1:1 to 0:1, 10 CV). The product containing fractions were evaporated to dryness and loaded on to a 1500 g Redisep Isco silica column and eluted with a gradient of 0 to 40% ethyl acetate in cyclohexane. The clean, product containing fractions were evaporated to an off white solid (15.41 g). LCMS (Method C): Rt=0.68, MH+=172

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

Reference:
Patent; Demont, Emmanuel Hubert; Garton, Neil Stuart; Gosmini, Romain Luc Marie; Hayhow, Thomas George Christopher; Seal, Jonathan; Wilson, David Matthew; Woodrow, Michael David; US2012/208798; (2012); A1;,
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Related Products of 50667-69-1, A common heterocyclic compound, 50667-69-1, name is 2,2,2-Trifluoro-N-(hydroxymethyl)acetamide, molecular formula is C3H4F3NO2, 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 l-chloro-2-nitrobenzene (10.0 g, 0.063 mmol) in cone, sulphuric acid (150 mL) was added N-hydroxy methyl trifluoro acetamide (9.98 g, 0.069 mmol). The reaction mixture was heated at 70-80C for 24 h. The reaction mass was quenched in ice cold water, neutralised with sodium hydroxide and extracted with DCM. The organic layer was concentrated and the obtained crude product was purified by column chromatography on silica gel eluting with 4% EtOAc: pet. ether to afford 5.5 g of desired product. 1H NMR (300 MHz, DMSO d6): 4.48 (d, J = 3.9 Hz, 2H), 7.62- 7.64 (m, 1H), 7.72- 7.78 (m, 1H), 7.97- 8.01 (m, 1H), 10.09 (brs, 1H) .

The synthetic route of 50667-69-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLENMARK PHARMACEUTICALS S.A.; GHARAT, Laxmikant Atmaram; MUTHUKAMAN, Nagarajan; KHAIRATKAR-JOSHI, Neelima; KATTIGE, Vidya Ganapati; WO2013/186692; (2013); A1;,
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108-13-4, name is Malonamide, 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. Formula: C3H6N2O2

To a solution of malonic-acid diamide (1 g) in DMF (15 mL), N,N dimethylformamide-dimethylacetal (1.4 g) added slowly. Then the mixture heated up to 50 C. and stirred for 3 h. The product isolated after concentration the mixture followed by crystallization (410 mg).1H NMR. (DMSO d6) delta: 7.45 and 7.02 (each bs, 4H, 2¡Á-NH2), 7.40 (s, 1H, -CH), 2.94 and 2.89 (2¡Ás, each 3H, 2¡Á-NCH3).13C NMR (DMSO d6) delta: 169.16 and 169.15 (2¡ÁCO), 151.08 (-HN-CH), 96.37 (C qvat.), 43.07 and 42.95 (2¡ÁNCH3).

The synthetic route of 108-13-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Dekany, Gyula; Agoston, Karoly; Bajza, Istvan; B¡ãjstrup, Marie; Kroeger, Lars; US2009/234111; (2009); A1;,
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Application of 89976-75-0, 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. 89976-75-0, name is 6-Amino-2H-1,4-benzoxazin-3(4H)-one belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

45.iii) 6-[(S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-hydroxy-propylamino]-4H-benzo[1,4]oxazin-3-oneTo a solution of tert-butyl-dimethyl-((S)-1-oxiranylmethoxy)-silane (commercial; 13.0 g, 69 mmol) in MeCN (220 mL) was added LiClO4 (22 g, 207 mmol). 6-Amino-4H-benzo[1,4]oxazin-3-one (commercial; 11.45 g, 64 mmol) was added and the mixture was stirred at 50¡ã C. for 6 h. The solvent was removed in vacuo and the residue was purified by CC (DCM/MeOH/NH4OH 1000/25/2->1000/100/2) to afford the title compound as a pale brown foam (11.16 g, 44percent).(ESI, m/z): 353.3 [M+H+].

The synthetic route of 6-Amino-2H-1,4-benzoxazin-3(4H)-one has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Actelion Pharmaceuticals Ltd; US2011/39823; (2011); 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 147751-16-4 as follows. name: tert-Butyl methylsulfonylcarbamate

1.6 M n-Butyl lithium in hexanes (20.2 ml, 32.4 mmol) was added drop wise to a solution of N,N-diisopropylethylamine (5.91 ml, 33.9 mmol) in 25 ml dry THF in ice bath and stirred for 30 minutes. Then tert-butyl methylsulfonylcarbamate in 25 ml dry THF was added slowly and stirred at 0 C. for 1 hour. The mixture was then cooled to -78 C. and 4-phenoxy-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde (3.01 g, 15.4 mmol) in 25 ml dry THF was added slowly. The reaction was slowly warmed up to room temperature and stirred at room temperature for 1 hour. Then it was quenched with water, acidified with 1N HCl to pH 3, extracted with ethyl acetate. The combined organic layer was then dried over Na2SO4, filtered and concentrated. Column purification gave 1 g product as off-white solid. 1H NMR (DMSO-d6, 300 MHz) delta ppm 11.34 (s, 1H), 9.39 (s, 1H), 7.54 (d, J=8.10 Hz, 1H), 7.42-7.37 (m, 2H), 7.28 (d, J=2.40, 1H), 7.22-7.12 (m, 2H), 7.03-7.01 (m, 2H), 5.43 (dd, J=9.3, 1.8 Hz, 1H), 4.01 (dd, J=13.5, 2.1 Hz, 1H), 3.54 (dd, J=14.7, 9.3 Hz, 1H), 1.42 (s, 9H). MS (ESI) m/z 418 [M-H]-.

According to the analysis of related databases, 147751-16-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Anacor Pharmaceuticals, Inc.; GlaxoSmithKline; US2010/256092; (2010); A1;,
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Adding a certain compound to certain chemical reactions, such as: 402-46-0, name is 4-Fluorobenzenesulfonamide, 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 402-46-0, Recommanded Product: 4-Fluorobenzenesulfonamide

General procedure: To a round-bottom flask (100 mL) that contained a solution of aryl sulfonamide (5 mmol), DMAP (5 mmol), and EDCI, (5mmol) in CH2Cl2 (50 mL) was added the synthesized cinnamic acid 5-7 (5 mmol) at room temperature. The resulting mixture was stirred at room temperature for overnight, then cooled to 5 , and acidified to pH 1 with addition of HCl aqueous solution (10%), which was followed by extraction with CH2Cl2/MeOH (9:1, 3 ¡Á 100 mL). The combined organic layers were washed with H2O and brine, dried over Na2SO4, and concentrated in vacuo. The residue was subjected to silica gel chromatography or crystallization if necessary to afford the compounds (5a-7e). Crystallographical and experimental data of compounds 5b and 6c were summarized in Table 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, 4-Fluorobenzenesulfonamide, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Luo, Yin; Zhou, Yang; Song, Yanhua; Chen, Guo; Wang, Yu-Xiang; Tian, Ye; Fan, Wei-Wei; Yang, Yu-Shun; Cheng, Tao; Zhu, Hai-Liang; Bioorganic and Medicinal Chemistry Letters; vol. 28; 23-24; (2018); p. 3634 – 3638;,
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These common heterocyclic compound, 15441-10-8, name is 3-(Aminosulfonyl)propanoic acid, 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. name: 3-(Aminosulfonyl)propanoic acid

General procedure: To a solution of 3-(4-((2-aminopropyl)thio)-1 ,2,5-oxadiazol-3-yl)-4-(3-(difluoromethyl)-4- fluorophenyl)-1 ,2,4-oxadiazol-5(4H)-one hydroiodide (Int 102) (416 mg, 0.81 mmol), HATU (462 mg, 1 .22 mmol) and Et3N (245 mg, 2.43 mmol) in DMF (8 mL) 2- sulfamoylacetic acid (135 mg, 0.97 mmol) was added and the mixture was stirred at rt overnight. EtOAc (20 mL) was added and the mixture was extracted with water (2 x 20 mL). The combined organic layers were dried over anhydrous Na2S0 , filtered and concentrated to dryness. The residue was purified by column chromatography to give the title compound as a white solid.

The synthetic route of 3-(Aminosulfonyl)propanoic acid has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PHENEX DISCOVERY VERWALTUNGS-GMBH; STEENECK, Christoph; KINZEL, Olaf; ANDERHUB, Simon; HORNBERGER, Martin; KLEYMANN, Gerald; HOFFMANN, Thomas; (191 pag.)WO2018/83241; (2018); 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 193751-54-1 as follows. Safety of tert-Butyl cyclopent-3-en-1-ylcarbamate

To a stirred suspension of LiAlH4 (3.74 g, 0.09852 mol) in 200 ml anhydrous THF in a two neck RBF (IL), 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).

According to the analysis of related databases, 193751-54-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Alnylam Pharmaceuticals, Inc.; Fitzgerald, Kevin; Butler, James; Bettencourt, Brian; Borodovsky, Anna; Kuchimanchi, Satyanarayana; Charisse, Klaus; Manoharan, Muthiah; Maier, Martin; Rajeev, Kallanthottathil G.; Foster, Donald; US2015/247143; (2015); A1;,
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