Tag: M.W=100-200

354-38-1, 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 354-38-1 as follows.

2-Methyl-2-(methylsulfinyl)propanenitrile (Int-3, 9.8 g, 74.7 mmol) was dissolved in dichloromethane (390 mL) at 0-5C (ice bath) and 2,2,2-trifluoroacetamide (17.0 g, 151 mmol), magnesium oxide (12.7 g, 307 mmol) and rhodium(II) acetate dimer (850 mg, 1.92 mmol) were added subsequently. Finally, a solution of iodobenzene diacetate (36.3 g, 113 mmol) in dichloromethane (98.0 mL) was added and the mixture was stirred for 1 h at 0-5C, followed by 6 h at room temperature. Then, a second portion of rhodium(II) acetate dimer (850 mg, 1.92 mmol) was added and the suspension stirred for additional 95 h at room temperature. The reaction mixture was filtered, the residue was washed with dichloromethane (100 mL) and the combined filtrate was concentrated in vacuo to afford a dark oil as crude product. After column chromatography (silica gel, 100 g, eluting with ethyl acetate / n-heptane, gradient 10:90 to 50:50) and drying in vacuo (50C, 5 mbar) the title compound was isolated as a light yellow oil, that solidified upon standing (13.74 g, 76%). HPLC (method LCMS_fglm) tR = 0.97 min. 1H NMR (CDC13, 400 MHz): delta 1.91 (s, 3 H), 1.91 (s, 3 H), 3.65 (s, 3 H). MS (ES-) m/z 241.1 [M-H] ,

According to the analysis of related databases, 2,2,2-Trifluoroacetamide, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BARTELS, Bjoern; CUENI, Philipp; DOLENTE, Cosimo; GUBA, Wolfgang; HAAP, Wolfgang; KUGLSTATTER, Andreas; OBST SANDER, Ulrike; PETERS, Jens-Uwe; ROGERS-EVANS, Mark; VIFIAN, Walter; WOLTERING, Thomas; (231 pag.)WO2016/55496; (2016); A1;,
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A common heterocyclic compound, 630-22-8, name is 2,2-Dimethylpropanethioamide, molecular formula is C5H11NS, 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. 630-22-8.

Intermediate 23: 2-Propen-1-yl {3-[5-(2-chloro-4-pyrimidinyl)-2-(1,1-dimethylethyl)-1,3-thiazol-4-yl]-2-fluorophenyl}carbamate; To a solution of 2-propen-1-yl {3-[(2-chloro-4-pyrimidinyl)acetyl]-2-fluorophenyl}carbamate (30 g, 85.9 mmol) (Intermediate 20) in DMA (300 mL), NBS (15.3 g, 85.9 mmol) was added. The reaction mixture was stirred at rt for 1 h. Then 2,2-dimethylpropanethioamide (11.0 g, 94.5 mmol) was added at 0 C. The mixture was stirred at rt for 2 h. The mixture was poured into water and extracted with EtOAc (200 mL¡Á3). The combined organic layers were washed with water and brine successively, dried over Na2SO4, filtered and concentrated under reduced pressure to give the crude product, which was purified by column chromatography on silica gel (DCM:petroleum ether 2:1) to afford the title compound. (11 g, 35.4% yield). 1H NMR (400 MHz, CDCl3) delta ppm 8.29 (d, J=5.27 Hz, 1H), 8.12-8.19 (m, 1H), 7.12-7.25 (m, 2H), 6.80-6.88 (m, 2H), 5.85-5.98 (m, 1H), 5.20-5.37 (m, 2H), 4.61-4.67 (m, 2H). MS (ES+): 447 [M+H]+.

The synthetic route of 2,2-Dimethylpropanethioamide has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Adams, Jerry Leroy; Dickerson, Scott Howard; Johnson, Neil W.; Kuntz, Kevin; Petrov, Kimberly; Ralph, Jeffrey M.; Rheault, Tara Renae; Schaaf, Gregory; Stellwagen, John; Tian, Xinrong; Uehling, David Edward; Waterson, Alex Gregory; Wilson, Brian; US2009/298815; (2009); A1;,
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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. 2832-19-1, name is 2-Chloro-N-(hydroxymethyl)acetamide, This compound has unique chemical properties. The synthetic route is as follows., 2832-19-1

(d) 2-Nicotinyl-4-tert-butyl-6-(N-alpha-chloroacetoaminomethyl)phenol 450 mg of the compound obtained in Example 3 (c) above was dissolved in 2 ml of a mixed solvent of acetic acid: sulfuric acid (1:1 by volume), and 330 mg of N-hydroxymethyl alpha-chloroacetamide was added to the solution. The mixture was then stirred at 60 C. for 2 hours and at 80 C. for 1 hour and poured into water. The mixture was extracted with ethyl acetate, and the ethyl acetate layer was washed successively with water and an aqueous sodium chloride solution, dried and concentrated. The residue was chromatographed on silica gel column using a mixed solvent of methylene chloride: ethyl acetate (5:1 by volume) to obtain 390 mg of the title compound having the following physical properties. TLC (methylene chloride: ethyl acetate=1:2): Rf=0.30. IR (chloroform solution): nu=3430, 2960, 1670, 1630, 1590, 1530, 1460, 1415, 1370, 1345, 1275, 1250, 1130, 1100, 1055, 1020, 995 cm-1. NMR (CDCl3 solution): delta=12.10 (1H, s), 8.47-8.85 (2H, m), 7.70-8.00 (1H, m), 7.10-7.60 (4H, m), 4.48 (2H, d, J=6 Hz), 3.98 (2H, s), 1.23 (9H, s). MS: m/e=360 (M+).

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Reference:
Patent; Ono Pharmaceutical Co., Ltd.; US4245099; (1981); A;,
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 2675-89-0 as follows. 2675-89-0

General procedure: To a suspension of NaH (344 mg, 60% dispersion in mineral oil) in THF (17 mL) was added allyl alcohol (2) (500 mg, 8.6 mmol) at 0 C. After 1 h at the same temperature, chloroacetamide 1 (0.97 mL, 9.5 mmol) was added and the mixture was stirred for 24 h. The mixture was quenched with saturated aqueous NH4Cl and concentrated at reduced pressure. The resulting residue was dissolved in EtOAc and washed with water and brine. The organic layer was dried over anhydrous MgSO4 and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (hexanes/EtOAc, 3:1) to give 6a (1.05 g, pale yellow oil) in 85% yield.

According to the analysis of related databases, 2675-89-0, the application of this compound in the production field has become more and more popular.

Reference:
Article; Yun, Jeong In; Kim, Hyoung Rae; Kim, Sang Kyum; Kim, Deukjoon; Lee, Jongkook; Tetrahedron; vol. 68; 4; (2012); p. 1177 – 1184;,
Amide – Wikipedia,
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588-46-5, Adding some certain compound to certain chemical reactions, such as: 588-46-5, name is N-Benzylacetamide, 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 588-46-5.

General procedure: Amide 1 (0.25 mmol, 1 equiv.) and Selectfluor (0.625 mmol, 2.5 equiv.) were dissolved in acetonitrile (5 mL) at room temperature, and CuBr (0.3 mmol, 1.2 equiv.) was added over a 40 min period in 6 portions. After all the CuBr was added, the resulting mixture was stirred for extra 20 min, and then acetonitrile was evaporated under reduced pressure. Saturated ammonium chloride solution (20 mL) was added into reaction mixture and extracted with diethyl ether (25 mL ¡Á 4); the ether layers were combined and dried over Na2SO4, filtered, evaporated under reduced pressure to give the crude product. Silica gel flash chromatography of the crude product [hexanes-ethyl acetate (10:1) to hexanes-ethyl acetate (4:1)] yielded pure imide 2.

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 588-46-5.

Reference:
Article; Jin, Zhuang; Xu, Bo; Hammond, Gerald B.; Dimagno, Stephen G.; Journal of Fluorine Chemistry; vol. 143; (2012); p. 226 – 230,5;,
Amide – Wikipedia,
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16066-84-5, These common heterocyclic compound, 16066-84-5, name is tert-Butyl methylcarbamate, 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.

tert-butyl [4′-(3,4-dimethyl-2-oxo-2,3-dihydro-benzoxazole-6-carbonyl)-4-(2-oxo-2,3-dihydro-imidazo[4,5-b]pyridin-1-yl)-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-6′-yl]-methyl-carbamate Under an argon atmosphere 13 mg (0.96 mmol) tert-butyl methyl-carbamate, 11 mg (0.019 mmol) Xantphos, 8.8 mg (0.010 mmol) Pd2 dba3 and 47 mg (0.15 mmol) caesium carbonate were added to 50 mg (0.10 mmol) 1-[6′-chloro-4′-(3,4-dimethyl-2-oxo-2,3-dihydro-benzoxazole-6-carbonyl)-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-yl]-1,3-dihydro-imidazo[4,5-b]pyridin-2-one in 1.00 mL dioxane and the mixture was refluxed for 15 h with stirring. The reaction mixture was evaporated down i. vac. and the residue obtained was used in the next step without further purification. Yield: 59 mg (quantitative) Rt (HPLC): 1.70 min (method B)

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 16066-84-5.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2011/59954; (2011); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

67442-07-3, A common heterocyclic compound, 67442-07-3, name is 2-Chloro-N-methoxy-N-methylacetamide, molecular formula is C4H8ClNO2, 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.

A mixture of 1-benzyl-piperazine (1.0 g, 5.67 mmol), 2-chloro-LambdaA-methylacetamide (671.2 mg, 6.24 mmol, 1.1 eq.), and potassium carbonate (941 mg, 6.81 mmol, 1.2 eq.) in anhydrous THF (23 mL) was stirred at 60 0C under N2 for 18 h. The mixture was cooled to rt and poured into EtOAc. The organic phase was washed with water and brine, dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by MPLC(Biotage.(R)., gradient elution 1:4:5 v/v MeOH:Acetone:DCM) to give 1.16 g (83percent) of the product as a white solid. 1H-NMR (300 MHz, DMSO-alphafe) .delta 7.62 to 7.56 (broad d, 1H),7.33 to 7.20 (m, 5H), 3.45 (s, 2H), 2.85 (s, 2H), 2.58 (d, 3H), 2.44 to 2.33 (broad s, 8H);ES-MS m/z 248.2 [M+H]+, RT (min) 0.33.

The synthetic route of 67442-07-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER PHARMACEUTICALS CORPORATION; WO2007/56170; (2007); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

61903-11-5, 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. 61903-11-5, name is 1-(1,4-Diazepan-1-yl)ethanone, A new synthetic method of this compound is introduced below.

iii) 5-(4-acetyl-[1,4]diazepan-1-yl)-pentanoic acid [5-(4-methoxy-phenyl)-1H-pyrazol-3-yl]-amide5-bromo-pentanoic acid [5-(4-methoxy-phenyl)-1H-pyrazol-3-yl]amide (1.5 g, 4.26 mmol) was dissolved in DMF (15 mL), and sodium iodide (0.64 g, 4.26 mmol) was added followed by N-acetylhomopiperazine (0.56 mL, 4.26 mmol) and diisopropylethylamine (0.74 mL, 4.26 mmol). The reaction was stirred under N2 at 50 C. for 18 hrs. Upon reaction completion (as monitored by LCMS), the solvent was removed at reduced pressure and the resulting oily residue was dissolved in DCM (20 mL), washed with sat. Na2CO3 (2¡Á20 mL) and sat. NaCl (2¡Á20 mL), and dried over Na2SO4. Upon solvent removal, 1.7 g of crude product as a thick oil were obtained. The product was purified by SiO2 chromatography (10 g cartridge-flash SI II from IST) employing DCM and DCM:MeOH 9:1 to yield 0.92 g of pure product and 0.52 g of less pure product. A second purification of the impure fractions using a 5 g SiO2 cartridge was performed using the same eluent. Overall, 1.09 g of 5-(4-acetyl-[1,4]diazepan-1-yl)-pentanoic acid [5-(4-methoxy-phenyl)-1H-pyrazol-3-yl]-amide were obtained (2.64 mmol, 62% yield) as a thick light yellow oil. MS (ES+): 414.26 (M+H)+.

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; WYETH; SIENA BIOTECH S.P.A.; US2009/181953; (2009); 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. 2675-89-0, name is 2-Chloro-N,N-dimethylacetamide, This compound has unique chemical properties. The synthetic route is as follows., 2675-89-0

To a stirred suspension of N-(4-(3-(5-tert-butylisoxazol-3- yl)ureido)phenyl)-5-(pyrrolidin-3-yloxy)picolinamide hydrochloride (150 mg, 0.30 mmol) in CH3CN (3 mL) was added TEA (126 muEpsilon, 0.90 mmol), KI (10 mg,0.060mmol), and 2-chloro-N,N-dimethylacetamide (21 muEpsilon , 0.30 mmol). The resulting mixture was heated at 85 C for 1 h. LC-MS indicated that the reaction was complete. The reaction mixture was evaporated under reduced pressure and the residue was purified by reverse phase HPLC to give N-(4-(3-(5-tert-butylisoxazol-3- yl)ureido)phenyl)-5 -( 1 -(2-(dimethylamino)-2-oxoethyl)pyrrolidin-3 – yloxy)picolinamide (110 mg, 67%). LC-MS (ESI) m/z 550 (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; AMBIT BIOSCIENCES CORPORATION; LIU, Gang; WO2011/150198; (2011); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

1197-22-4, Adding some certain compound to certain chemical reactions, such as: 1197-22-4, name is N-Phenylmethanesulfonamide, 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 1197-22-4.

A solution of N-phenylmethanesulfonamide (0.800 g, 4.673 mmol), sodium hydride (60.00 %, 0.224 g, 5.607 mmol) and methyl 4-(bromomethyl)-3-fluorobenzoate (1.270 g, 5.140 mmol) in N,N-dimethylformide (10 mL) was stirred at the room temperature for 5 hr. Then, water was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with aqueous saturated sodium chloride solution, dried with anhydrous Mg504, filtered, and concentrated in vacuo. The residue was chromatographed (5i02, 12 g cartridge; ethyl acetate / hexane = 0 % to 50 %) togive methyl 3-fluoro-4-((N-phenylmethylsulfonamido)methyl)benzoate as yellow solid(0.752 g, 47.7 %).

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 1197-22-4.

Reference:
Patent; CHONG KUN DANG PHARMACEUTICAL CORP.; LEE, Jaekwang; HAN, Younghue; KIM, Yuntae; CHOI, Daekyu; MIN, Jaeki; BAE, Miseon; YANG, Hyunmo; KIM, Dohoon; (644 pag.)WO2017/18803; (2017); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics