Category: amides-buliding-blocks

Reference of 112257-19-9, These common heterocyclic compound, 112257-19-9, name is tert-Butyl methyl(2-(methylamino)ethyl)carbamate, 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.

Step 6: tent-Butyl (2-(((3-iodo-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-4-yl)methyl)(methyl)amino)ethyl)(methyl)carbamate [0204] 3-iodo-1-(oxan-2-yl)-1H-pyrazole-4-carbaldehyde (21.5 g, 70.24 mmol, 1.00 equiv), tert-butyl N-methyl-N-(2-(methylamino)ethyl)carbamate (20 g, 106.23 mmol, 1.51 equiv) and NaBH(OAc)3 (29.8 g, 137.98 mmol, 1.96 equiv) in dichloroethane (300 mL) was stirred for 1 h at room temperature. The reaction was diluted with 300 mL of dichloromethane and then washed with 3¡Á300 mL of brine. The organic layer was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was purified on a silica gel column eluted with 0-7percent methanol in dichloromethane to give 31 g (92percent) of tert-butyl (2-(((3-iodo-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-4-yl)methyl)(methyl)amino)ethyl)(methyl)carbamate as a yellow oil. 1H NMR (300 MHz, CDCl3): delta 7.62 (s, 1H), 5.34-5.30 (m, 1H), 4.06-4.02 (m, 1H), 3.68-3.62 (m, 1H), 3.42-3.38 (m, 4H), 2.85 (s, 4H), 2.62-2.53 (m, 2H), 2.47-2.46 (m, 2H), 2.13-1.97 (m, 3H), 1.74-1.69 (m, 3H), 1.46 (s, 9H) ppm. LCMS (method A, ESI): RT=1.17 min, m/z=479.0 [M+H]+.

The synthetic route of 112257-19-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Epizyme, Inc.; Mitchell, Lorna Helen; Shapiro, Gideon; Chesworth, Richard; Boriack-Sjodin, Paula Ann; Moradei, Oscar Miguel; US2014/288140; (2014); A1;,
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Reference of 1015-89-0, 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 1015-89-0 as follows.

Phenanthridin-6(5H)-one (1; 1.017 g, 5.209 mmol) was placed in aSchlenk flask under argon. Freshly distilled CH2Cl2 (30 mL) was added,and the resulting solution was cooled to 0 C. Tf2O (3.00 g, 1.74 mL,10.6 mmol, 2.0 equiv) was added dropwise to the suspension. After40 min, the mixture became almost completely homogeneous. After afurther 20 min of stirring, pyridine (0.414 g, 423 muL, 5.233 mmol, 1.02equiv) was slowly added and a precipitate formed. The resulting mixturewas stirred at 0 C for 40 min. Next, H2O (20 mL) was added andthe mixture was extracted with CH2Cl2 (2 ¡Á 30 mL). The organic layerwas dried (Na2SO4), filtered, and concentrated on a rotary evaporator.The resulting residue was dissolved in Et2O (10 mL) and hexane (60mL) was added. Most of the volatiles were then slowly removed on arotary evaporator. The resulting suspension was filtered to give abeige solid; 1.551 g (91%); mp 82-83 C (Et2O-hexane); Rf = 0.57(hexane-EtOAc, 5:1).IR (CHCl3): 3082, 3047, 1629, 1615, 1467, 1426, 1244, 1216, 1137,1023, 607 cm-1.1H NMR (600 MHz, acetone-d6): delta = 9.00 (ddt, J = 8.3, 1.1, 0.6 Hz, 1 H,H-6), 8.89 (ddt, J = 8.1, 1.4, 0.6 Hz, 1 H, H-11), 8.34 (ddd, J = 8.3, 1.4,0.7 Hz, 1 H, H-3), 8.19 (ddd, J = 8.3, 7.1, 1.4 Hz, 1 H, H-5), 8.11 (ddd,J = 8.0, 1.5, 0.7 Hz, 1 H, H-14), 8.02 (ddd, J = 8.3, 7.1, 1.1 Hz, 1 H, H-4),7.94 (ddd, J = 8.0, 7.1, 1.4 Hz, 1 H, H-13), 7.90 (ddd, J = 8.1, 7.1, 1.5 Hz,1 H, H-12).13C NMR (151 MHz, acetone-d6): delta = 152.50 (C-2), 141.70 (C-8),137.27 (C-10), 134.08 (C-5), 130.96 (C-13), 130.10 (C-4), 129.92 (C-14), 129.35 (C-12), 125.53 (C-7), 124.73 (C-3), 124.02 (C-6), 123.93(C-11), 119.50 (q, JC-F = 320 Hz, CF3), 119.10 (C-9).MS (ESI): m/z (%) = 350.1 [M + Na]+ (100).HRMS (ESI): m/z [M + H]+ calcd for C14H9F3NO3S: 328.0250; found:328.0250.

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:
Article; Sonawane, Manoj R.; Vavra, Jan; ?aman, David; Cisa?ova, Ivana; Teply, Filip; Synthesis; vol. 47; 22; (2015); p. 3479 – 3488;,
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Adding a certain compound to certain chemical reactions, such as: 6228-73-5, name is Cyclopropanecarboxamide, 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 6228-73-5, Recommanded Product: Cyclopropanecarboxamide

Mix the compound obtained in Step 2 (350 mg, 1.24 mmol), cyclopropanecarboxamide (116 mg, 1.36 mmol), (+-)-2,2′-bis(diphenylphosphino)-1,1′-binaphthalene (BINAP, 77 mg, 0.124 mmol), Cs2CO3 (1.01 g, 3.1 mmol) in 1,4-dioxane (30 mL), then under N2 atmosphere, add tris(dibenzylideneacetone)dipalladium [Pd2(dba)3, 113 mg, 0.124 mmol]. Stir the reaction at 126 C. under N2 for 16 hrs. Cool the reaction mixture, filter, and concentrate the filtrate under reduced pressure to give the crude product. Purification by chromatography (silica gel, EtOAc_PE=1:1) affords the title compound (178 mg, 43.3%). MS: (M+1): 332.2.

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, Cyclopropanecarboxamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Zhang, Deyi; Zhang, Ruihao; Zhong, Boyu; Shih, Chuan; US2015/197511; (2015); A1;,
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Application of 53297-70-4, 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 53297-70-4 as follows.

General procedure: The chlorides 9a-j was dissolved in CH2Cl2 (20 mL) andadded dropwise to a stirred solution of 4-anilinesulfonamide(10.0 mmol) and NaHCO3 (1.26 g, 15.0 mmol) in CH3CN(80 mL). The mixture was heated at 70 C for 2h. The solution solutionwas evaporated, and poured to water, filtered to give asolid. This was purified by chromatography on silica gelusing CH2C12-MeOH (30: l) to give the title molecules 10a-t.The typical compound 10c was characterized with NMR andMS techniques. The detailed data is below.

According to the analysis of related databases, 53297-70-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Song, Zhendong; Wang, Ping; Huang, Shanshan; Wang, Changyuan; Wang, Rui-Rui; Yang, Liu-Meng; Zhen, Yuhong; Liu, Kexin; Zheng, Yong-Tang; Ma, Xiaodong; Medicinal Chemistry; vol. 13; 4; (2017); p. 398 – 405;,
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Reference of 563-83-7,Some common heterocyclic compound, 563-83-7, name is Isobutyramide, molecular formula is C4H9NO, 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 solution of 2-methylpropanamide (6.53 g, 75.0 mmol) and 2,4-bis(4- methoxyphenyl)-1 ,3-dithia-2,4-diphosphetane-2,4-disulfide (15.17 g, 37.51 mmol) in THF (100 ml.) was heated to reflux for 4 h. The reaction mixture was then cooled to rt and poured into saturated aqueous NaHCOs (200 ml_). The mixture was extracted with ether (4 x 100 ml_). The organic fractions were combined, dried over Na2SO4, filtered, and concentrated. Purification by flash column chromatography (20% EtOAc:hexanes) afforded 4.77 g (62%) of the title compound of Step A. 1H NMR (400 MHz, CDCI3) delta 7.63 (br s, 1 H), 6.90 (br s, 1 H), 2.88 (m, 1 H), and 1.27 (d, 6H, J = 6.8 Hz).

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

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2009/32667; (2009); A1;,
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Some common heterocyclic compound, 610302-03-9, name is tert-Butyl (3-hydroxycyclohexyl)carbamate, molecular formula is C11H21NO3, 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. Formula: C11H21NO3

XV.2 3-Methylamino-cyclohexanol Prepared analogously to XII.2 from 0.933 g (3-hydroxy-cyclohexyl)-carbamic acid tert-butyl ester. Yield: 0.203 g

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 610302-03-9, its application will become more common.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2011/217311; (2011); A1;,
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Reference of 57957-24-1,Some common heterocyclic compound, 57957-24-1, name is N-(1-Phenylvinyl)acetamide, molecular formula is C10H11NO, 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.

Example 12. Asymmetric hydrogenation of different unsaturated hydrocarbon compounds with chiral ligand 6 and [Rh(nbd)2]BF4 at room temperature.The following compounds were hydrogenated in presence of a catalyst of the invention (ligand 6 and [Rh(nbd)2]BF4) at room temperature.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route N-(1-Phenylvinyl)acetamide, its application will become more common.

Reference:
Amide – Wikipedia,
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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. 1118-69-0, name is N-Isopropylacetamide, A new synthetic method of this compound is introduced below., Safety of N-Isopropylacetamide

Under nitrogen atmosphere, add 1 -(4-amidogen-2, 6-difluoro-phenyl)-3-N,N-dimethylammonium-2-fluoro-2-acrylketone (IV) (2.5 g, 10 mmol), N-isopropyl acetamide (2.0 g, 20 mmol), phosphorus trichloride (2.0 g, 13 mmol) and methylbenzene 50 mE, 0-5 C., and add triethylamine (2.0 g, 20 mmol) while stirring, and then, raise the temperature to 105-115 C. and conduct stirring operations for 3-5 hours. Reduce the pressure and recycle the solvent, and dissolve the leftovers with dichlormethane 100 mE, and wash with saturated sodium bicarbonate and water, and use anhydrous sodium sulfate for drying and concentration, and obtain yellow solid N-[2,6-difluoro-4-(3-N,N-dimethylam- monium-2-fluoro-2-acrylketone- 1 -yl)phenyl] -N?-isopropylethanamidine (V) 2.8 g, the yield rate is 85.6%; mass spectrum (El): mlz 328 (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; SUZHOU MIRACPHARMA TECHNOLOGY CO., LTD.; Xu, Xuenong; (9 pag.)US2017/305884; (2017); A1;,
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Electric Literature of 518057-72-2, 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 518057-72-2 as follows.

To 5-amino-2-fluoro-benzamide (37 mg, 0.24 mmol) and diisopropylethylamine (124 mu, 0.71 mmol) in dichloromethane (390 mu) cooled at 0 C was added dropwise a solution of 2-fluoro-6-(4- fluorophenoxy)-3-(trifluoromethyl)benzoyl chloride (80 mg, 0.24 mmol) in dichloromethane (390 mu). The reaction was stirred at room temperature for 1 hour. The solvent was evaporated and the residue was partitioned between water and ethyl acetate. The organic phase was concentrated to dryness. The residue was dissolved in 1ml of DMSO and purified by reverse phase HPLC to afford N-(3 -carbamoyl -4-fluoro- phenyl)-2-fluoro-6-(4-fluorophenoxy)-3-(trifluoromethyl)benzamide (25.5 mg, 24%). ESI-MS m/z calc. 454.08, found 455.1 (M+l)+; retention time (Method B): 1.63 minutes (3 minute run). l NMR (400 MHz, DMSO-d6) delta 11.05 (s, 1H), 7.98 (dd, J = 6.4, 2.8 Hz, 1H), 7.89 – 7.74 (m, 3H), 7.71 (s, 1H), 7.40 – 7.25 (m, 5H), 6.79 (d, J = 8.9 Hz, 1H) ppm.

According to the analysis of related databases, 518057-72-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; AHMAD, Nadia; ANDERSON, Corey; ARUMUGAM, Vijayalaksmi; ASGIAN, Iuliana, Luci; CAMP, Joanne, Louise; FANNING, Lev Tyler, Dewey; HADIDA RUAH, Sara, Sabina; HURLEY, Dennis; SCHMIDT, Yvonne; SHAW, David; SHETH, Urvi, Jagdishbhai; THOMSON, Stephen, Andrew; (691 pag.)WO2019/14352; (2019); A1;,
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Adding a certain compound to certain chemical reactions, such as: 533-17-5, name is N-(2-chlorophenyl)acetamide, 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 533-17-5, Formula: C8H8ClNO

General procedure: A mixture of N-phenylacetamide(2a, 135 mg, 1.0 mmol), iodine (254 mg, 1 mmol), TBHP (387 mg, 3.0 mmol, 70% in water) and toluene (2.0 mL) was added successively in a round-bottom flask, and the resulting soln. stirred for 24 h at 80 C. The mixture was then subjected to purification by preparative thin-layer chromatography (PE-EtOAc, 10:3) to afford product 3aa.

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-(2-chlorophenyl)acetamide, other downstream synthetic routes, hurry up and to see.

Reference:
Conference Paper; Chen, Cui; Liu, Weibing; Zhou, Peng; Beilstein Journal of Organic Chemistry; vol. 12; (2016); p. 2250 – 2255;,
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