Amides-buliding-blocks

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. 239074-29-4, name is tert-Butyl (trans-4-(hydroxymethyl)cyclohexyl)carbamate, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: tert-Butyl (trans-4-(hydroxymethyl)cyclohexyl)carbamate

b) ((1r,4r)-4-(tert-Butoxycarbonylamino)cyclohexyl)methyl 4-methylbenzene-sulfonate A solution of 4-methylbenzene-1-sulfonyl chloride (2.28 g, 11.96 mmol) in dichloromethane was added to a solution of tert-butyl (1r,4r)-4-(hydroxymethyl)cyclohexylcarbamate (Preparation 50a, 2.11 g, 9.2 mmol) and triethylamine (1.59 mL, 11.4 mmol) in dichloromethane (50 mL) and the mixture was stirred overnight at room temperature. The mixture was washed with 1 M aqueous sodium hydroxide solution and the organic layer was dried (MgSO4) evaporated and the residue was purified by flash chromatography (diethyl ether/hexanes) to give the title compound (2.91 g, 83%) as a white solid. LRMS (m/z): 382 (M-H)+.1 H NMR (300 MHz, CDCl3) delta ppm 0.90 – 1.12 (m, 4H), 1.43 (s, 3H), 1.78 (dd, 2H), 1.99 (d, 2H), 3.34 (m, 1H), 3.46 (t, 1H), 3.81 (d, 2H), 4.37 (m, 1H), 7.34 (d, 2H), 7.77 (d, 2H).

According to the analysis of related databases, 239074-29-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ALMIRALL, S.A.; EASTWOOD, Paul Robert; GONZALEZ RODRIGUEZ, Jacob; GOMEZ CASTILLO, Elena; BACH TANA, Jordi; WO2011/157397; (2011); A1;,
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Related Products of 113778-69-1,Some common heterocyclic compound, 113778-69-1, name is N-Methoxy-N-methylisobutyramide, molecular formula is C6H13NO2, 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 suspension of 1,1-dimethylethyl (3-methyl-2-pyridinyl)carbamate (3Og, 144mmol) in tetrahydrofuran (30OmL) at O0C under an atmosphere of nitrogen was added n-butyl-lithium (2.3M, 123mL) over 90 mins. After 30 mins at O0C lambda/,2-dimethyl-/V- (methyloxy)propanamide (22.7g, 173mmol) was added. After a further 60 mins at O0C the reaction was allowed to warm to ambient temperature and was added to 5M aqueous hydrochloric acid (30OmL) and heated to 600C for 1.5 h. The organic was separated. The aqueous was basified with 10M aqueous sodium hydroxide and extracted with ethyl acetate. The combined extracts were dried (MgSO4) and concentrated in vacuo to give the title compound as an orange crystalline solid (22.04g, 95%). LCMS rt = 2.38mins, MH+= 161

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

Reference:
Patent; GLAXO GROUP LIMITED; WO2008/34860; (2008); A1;,
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Application of 127-77-5, A common heterocyclic compound, 127-77-5, name is 4-Amino-N-phenylbenzenesulfonamide, molecular formula is C12H12N2O2S, 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: N1,N3-bis(4-(N-(5-methylisoxazol-3-yl)sulfamoyl)phenyl)malonamide (1). 5f (253 mg, 1 mmol) was dissolved in the solutionof THF (10 mL) and pyridine (1 mL) before 2a (240 mg, 2 mmol)wasdropwise added. Then the reaction mixture was stirred at roomtemperature overnight until the white solid was precipitated. Thecrude product was filtered and recrystallized with ethanol to give a1 as a light-yellow solid, yield 72%

The synthetic route of 127-77-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wang, Lei; Li, Li; Zhou, Zi-Han; Jiang, Zheng-Yu; You, Qi-Dong; Xu, Xiao-Li; European Journal of Medicinal Chemistry; vol. 136; (2017); p. 63 – 73;,
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Application of 1314538-55-0, 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 1314538-55-0 as follows.

[01253] A mixture of 4-chloro-2-cyclopropyl-6-(trifluoromethyl)pyrimidine (500 mg, 2.25 mmol, 1.00 equiv), potassium tert-butyl N-[(trifluoroboranuidyl)methyl]carbamate (600 mg, 2.53 mmol, 1.13 equiv), Pd(PPh3)2C12 (150 mg, 0.21 mmol, 0.01 equiv), and sodium carbonate (750 mg, 7.07 mmol, 3.15 equiv) in ethanol (20 mL)/water(2 mL) was stirred for 3 hours at 80C under nitrogen. The resulting mixture was concentrated under vacuum. The residue was purified by a silica gel colunm eluting with ethyl acetate/petroleum ether (1/4) to afford the title compound (250 mg, 35%) as greenish oil. LCMS [M+H] 318.

According to the analysis of related databases, 1314538-55-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; ESTRADA, Anthony; VOLGRAF, Matthew; CHEN, Huifen; KOLESNIKOV, Aleksandr; VILLEMURE, Elisia; VERMA, Vishal; WANG, Lan; SHORE, Daniel; DO, Steven; YUEN, Po-wai; HU, Baihua; WU, Guosheng; LIN, Xingyu; LU, Aijun; (537 pag.)WO2016/128529; (2016); A1;,
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Application of 631-58-3, 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. 631-58-3, name is Propanethioamide, This compound has unique chemical properties. The synthetic route is as follows.

Reference Example 28 4-[2-ethyl-4-(3-methylphenyl)-1,3-thiazol-5-yl]-2-pyridylamine A solution of 2-(2-amino-4-pyridyl)-2-bromo-1-(3-methylphenyl)ethanone hydrobromide (125 g, 0.323 mol) and thiopropionamide (28g, 0.314 mol) in N,N-dimethylformamide (1200 mL) was stirred at room temperature for 14 hrs. The solvent was evaporated under reduced pressure. Aqueous sodium hydrogen carbonate solution was poured into the residue and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogen carbonate solution, dried and concentrated. Crude crystals were washed with hexane-ethyl acetate = 1: 1 to give the title compound (76.0 g, yield 82%). melting point: 144-146C.

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

Reference:
Patent; Takeda Chemical Industries, Ltd.; EP1364949; (2003); A1;,
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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. 153248-46-5, name is [1-[(Boc-amino)methyl]cyclopropyl]methanol, A new synthetic method of this compound is introduced below., Recommanded Product: 153248-46-5

Step 3: Synthesis of diethyl l-[(l-{[(tert- butoxycarbonyl)amino]methyl}cyclopropyl)methyl]-1H-indole-2,6-dicarboxylateTo a solution of tert-butyl { [l-(hydroxymethyl)cyclopropyl]methyl}carbamate (20 g, 99.5 mmol), diethyl 1H-indole-2,6-dicarboxylate (26 g, 99.5 mmol) and triphenylphosphine (52 g, 199 mmol) in THF (300 mL) is added diisopropyl azodicarboxylate (31 mL, 199 mmol) at room temperature. The reaction mixture is stirred for 60 h and the solvent is evaporated. The residue is purified by flash column chromatography using 12% EtOAc in petroleum ether to afford a mixture of diethyl 1- [(l-{ [(tert-butoxycarbonyl)amino]methyl}cyclopropyl)methyl]-1H-indole-2,6- dicarboxylate and diethyl 1H-indole-2,6-dicarboxylate (36 g) as a white solid. The mixture is used in the next step without further purification.

The synthetic route of 153248-46-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BOYER, Stephen, James; GAO, Donghong, Amy; GUO, Xin; KIRRANE, Thomas, Martin, Jr.; SARKO, Christopher, Ronald; SNOW, Roger, John; SOLEYMANZADEH, Fariba; ZHANG, Yunlong; WO2011/71716; (2011); A1;,
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Application of 6228-73-5,Some common heterocyclic compound, 6228-73-5, name is Cyclopropanecarboxamide, molecular formula is C4H7NO, 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.

Step 3 To a reaction vial was added the product from Step 2 (20 mg, 0.056 mmol), cyclopropanecarboxamide (4.74 mg, 0.056 mmol) and BrettPhos (3.59 mg, 6.69 muiotaetaomicron) and the contents were purged with nitrogen before adding DMA (0.10 mL) and dioxane (0.20 mL). The resulting slurry was sparged with nitrogen for an additional minute, then Pd2(dba)3 (5.10 mg, 5.57 muiotaetaomicron) followed by LiHMDS (1 M in THF) (0.139 mL, 0.139 mmol) was added and the reaction vial was capped under nitrogen and placed into a preheated 110 C heating block and the mixture was allowed to stir at that temperature for 1.5h. After cooling, the reaction was quenched with MeOH, concentrated to remove the volatiles, and was purified by reverse phase preparative LCMS with the following conditions: Column: Waters XBridge C18, 19 x 200 mm, 5-muiotaeta particles; Mobile Phase A: 5:95 acetonitrile: water with 0.1% trifluoroacetic acid; Mobile Phase B: 95:5 acetonitrile: water with 0.1% trifluoroacetic acid; Gradient: 0-100% B over 20 minutes, then a 5-minute hold at 100% B; Flow: 20 mL/min. Fractions containing the desired product were combined and dried via centrifugal evaporation. The yield of the product (Example 29) was 15.4 mg (49%). HPLC (Method E) RT = 0.98 min. HPLC (Method G) RT = 0.76 min. LCMS observed MH+ = 408.2. 1H NMR (500MHz, DMSO-d6) delta 11.11 (br. s., 1H), 10.82 (br. s., 1H), 8.79 (br. s., 1H), 8.49 (s, 1H), 7.75 (d, J=6.7 Hz, 1H), 7.54 (d, J=7.9 Hz, 1H), 7.38 – 7.27 (m, 1H), 3.69 (s, 3H), 2.81 (d, J=4.3 Hz, 3H), 1.91 (br. s., 1H), 0.90 – 0.78 (m, 4H).

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

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; MOSLIN, Ryan M.; WEINSTEIN, David S.; WROBLESKI, Stephen T.; ZHANG, Yanlei; TOKARSKI, John S.; MERTZMAN, Michael E.; LIU, Chunjian; WO2015/69310; (2015); A1;,
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Related Products of 389890-43-1, 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. 389890-43-1, name is tert-Butyl (cis-3-hydroxycyclobutyl)carbamate, This compound has unique chemical properties. The synthetic route is as follows.

To a mixture of 2,3-dichloro-pyrazine ( 3.0 g, 20 mmol ) and tert-butyl ((1S,3S)- 3-hydroxycyclobutyl)carbamate (see PREPARATION 4A; 3.65 g, 20 mmol) in DMSO (50 mL) was added CS2CO3 ( 13.2 g, 40 mmol), and then the mixture was stirred at 80C overnight. The reaction mixture was diluted with water and filtered. The filter cake was washed with water, and dried to give tert-butyl ((lS,3S)-3-((3-chloropyrazin-2-yl)oxy)cyclobutyl)carbamate (5.7 g, 19.0 mmol, 96.6%). ESI-MS (M+l): 300 calc. for Ci3Hi8ClN303 299.

The chemical industry reduces the impact on the environment during synthesis tert-Butyl (cis-3-hydroxycyclobutyl)carbamate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; AMGEN INC.; ALLEN, Jennifer; FROHN, Michael; HARRINGTON, Paul; PICKRELL, Alexander; RZASA, Robert; SHAM, Kelvin; HU, Essa; WO2011/143366; (2011); A1;,
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Adding a certain compound to certain chemical reactions, such as: 114790-39-5, name is Benzyl (2,2-dimethoxyethyl)carbamate, 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 114790-39-5, Recommanded Product: Benzyl (2,2-dimethoxyethyl)carbamate

Example 1B benzyl allyl(2,2-dimethoxyethyl)carbamate The product of Example 1A (281.0 g, 1.18 mol) in dry toluene (1.0 L) was treated with powdered KOH (291.2 g, 5.20 mol) and triethylbenzylammonium chloride (4.4 g, 0.02 mol). A solution of allyl bromide (188.7 g, 1.56 mol) in toluene (300 mL) was then added dropwise over 1 hour at 20-30 C. The mixture was stirred overnight at room temperature and then water (300 mL) was added over 20 minutes at 20-30 C. The layers were separated and the aqueous phase was extracted with toluene (2*300 mL). The organic phases were combined, washed with brine (2*100 mL), dried (K2CO3), filtered and the filtrate concentrated to provide the title compound. 1H NMR (MeOH-d4, 300 MHz) delta 3.32 (s, 3H) 3.37 (m, 5H), 3.97 (d, J=5.4 Hz, 2H), 4.40-4.50 (m, 1H), 5.15 (m, 4H), 5.75 (m, 1H), 7.23 (m, 5H); MS (DCI/NH3) m/z 297 (M+NH4)+, 280 (M+H)+.

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; Buckley, Michael J.; Ji, Jianguo; US2005/261348; (2005); A1;,
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Synthetic Route of 98-64-6, These common heterocyclic compound, 98-64-6, name is 4-Chlorobenzenesulfonamide, 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: The prepared TfOH-SiO2 (60 mg, containing 0.05 mmol TfOH) was added to the toluene (2 mL) solution of alkene (2 mmol or 4 mmol) and sulfonamide (1 mmol) and the reaction mixture was stirred at 70 oC (or 85 oC). The course of the reaction was monitored by TLC. After the completion of the reaction, the mixture was cooled to room temperature and the reactor was centrifuged (2000 r/min) for 2 min and the solution was removed by syringe. The catalyst was then washed with toluene (1 mL) twice with the same procedure and a new reaction was carried out by adding the new batch of alkene (2 mmol), sulfonamide (1 mmol) and toluene (2 mL) to the recovered catalyst. The solution containing the product was purified through a silica gel flash column to afford the product.

The synthetic route of 98-64-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Liu, Pei Nian; Xia, Fei; Zhao, Zheng Le; Wang, Qing Wei; Ren, Yu Jie; Tetrahedron Letters; vol. 52; 46; (2011); p. 6113 – 6117;,
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