Category: amides-buliding-blocks

Some common heterocyclic compound, 3984-14-3, name is N,N-Dimethylsulfamide, molecular formula is C2H8N2O2S, 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: N,N-Dimethylsulfamide

1H-Indole-6-carboxamide, 2-bromo-3-cyclohexyl-N-[(dimethylamino)sulfonyl]-.; 1,1′-Carbonyldiimidazole (1.17 g, 7.2 mmol) was added to a stirred solution of 2-bromo-3-cyclohexyl-1H-indole-6-carboxylic acid (2.03 g, 6.3 mmol) in THF (6 mL) at 22 C. The evolution of CO2 was instantaneous and when it slowed the solution was heated at 50 C. for 1 hr and then cooled to 22 C. N,N-Dimethylsulfamide (0.94 g, 7.56 mmol) was added followed by the dropwise addition of a solution of DBU (1.34 g, 8.8 mmol) in THF (4 mL). Stirring was continued for 24 hr. The mixture was partitioned between ethyl acetate and dilute HCl. The ethyl acetate layer was washed with water followed by brine and dried over Na2SO4. The extract was concentrated to dryness to leave the title product as a pale yellow friable foam, (2.0 g, 74%, >90% purity, estimated from NMR). 1H NMR (300 MHz, DMSO-D6) delta ppm 1.28-1.49 (m, 3 H) 1.59-2.04 (m, 7 H) 2.74-2.82 (m, 1 H) 2.88 (s, 6 H) 7.57 (dd, J=8.42, 1.46 Hz, 1 H) 7.74 (d, J=8.78 Hz, 1 H) 7.91 (s, 1 H) 11.71 (s, 1 H) 12.08 (s, 1 H).; An alternative method for the preparation of 1H-indole-6-carboxamide, 2-bromo-3-cyclohexyl-N-[(dimethylamino)sulfonyl]- is described below.; To a 1 L four necked round bottom flask equipped with a mechanical stirrer, a temperature controller, a N2 inlet, and a condenser, under N2, was added 2-bromo-3-cyclohexyl-1H-indole-6-carboxylic acid (102.0 g, 0.259 mol) and dry THF (300 mL). After stirring for 10 min, CDI (50.3 g, 0.31 mol) was added portion wise. The reaction mixture was then heated to 50 oC for 2 h. After cooling to 30 oC, N,N-dimethylaminosulfonamide (41.7 g, 0.336 mol) was added in one portion followed by addition of DBU (54.1 mL, 0.362 mol) drop wise over a period of 1 h. The reaction mixture was then stirred at rt for 20 h. The solvent was removed in vacuo and the residue was partitioned between EtOAc and 1 N HCl (1:1, 2 L). The organic layer was separated and the aqueous layer was extracted with EtOAc (500 mL). The combined organic layers were washed with brine (1.5 L) and dried over MgSO4. The solution was filtered and concentrated in vacuo to give the crude product (111.0 g). The crude product was suspended in EtOAc (400 mL) at 60 oC. To the suspension was added heptane (2 L) slowly. The resulting suspension was stirred and cooled to 0 oC. It was then filtered. The filter cake was rinsed with small amount of heptane and house vacuum air dried for 2 days. The product was collected as a white solid (92.0 g, 83%). 1H NMR (MeOD, 300 MHz) delta 7.89 (s, H), 7.77 (d, J=8.4 Hz, 1H), 7.55 (dd, J=8.4 and 1.8 Hz, 1H), 3.01 (s, 6H), 2.73-2.95 (m, 1H), 1.81-2.05 (m, 8H), 1.39-1.50 (m, 2H); m/z 429 (M+H)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3984-14-3, its application will become more common.

Reference:
Patent; Bristol-Myers Squibb Company; US2008/188458; (2008); A1;,
Amide – Wikipedia,
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Related Products of 146651-75-4, A common heterocyclic compound, 146651-75-4, name is tert-Butyl (2-aminophenyl)carbamate, molecular formula is C11H16N2O2, 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 1: tert-Butyl 2-(6-chloronicotinamido)phenylcarbamate (94)To solution of (2-amino-phenyl)-carbamic acid tert-butyl ester (22) (Seto, C. T.; Mathias, J. P.; Whitesides, G. M.; J. Amer. Chem. Soc., (1993), 115, 1321-1329.) (1.56 g, 7.49 mmol) in MeCN (40 mL) is added triethylamine (2.60 mL, 18.7 mmol) and 6-chloronicotinic acid (1.42 g 8.99 mmol). The mixture is stirred for 18 h at r.t. Upon completion of the reaction, the solvent is removed in vacuo and the residue is partitioned between EtOAc and an NH4Cl solution. The organic phase is collected and the aqueous layer is then extracted with EtOAc; the combined organic layers are washed with brine, dried over MgSO4 and evaporated. The residue is purified by flash chromatography using EtOAc/Hexane (a gradient of 20:80 to 50:50) as an eluent, to afford the title compound 94 (2.39 g, 92% yield). 1H NMR (DMSO-d6) delta (ppm): 10.01 (s, 1H), 8.96 (d, J=2.0 Hz, 1H), 8.71 (s, 1H), 8.35 (dd, J=8.4, 2.4 Hz, 1H), 7.73 (d, J=8.0 Hz, 1H), 7.62 (d, J=8.0 Hz, 1H), 7.48 (d, J=7.6 Hz, 1H), 7.22 (td, J=7.8, 1.4 Hz, 1H), 7.13 (t, J=7.6 Hz, 1H), 1.44 (s, 9H). LRMS (ESI): (calc) 347.10 (found) 370.1 (M+Na+).

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; METHYLGENE INC.; US2008/227826; (2008); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

These common heterocyclic compound, 4815-28-5, name is 2-Amino-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxamide, 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. Quality Control of 2-Amino-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxamide

To a stirred solution of the appropriate aminothiophene (1 equiv. ) in 1,4-dioxane (5ml per mmol of aminothiophene) was added the appropriate acyl chloride (1.2 equiv. ). The reaction mixture was stirred at room temperature for 17 hours and then diluted with ether or hexane. The resultant precipitate was removed by filtration, washed with ether and air- dried to give the desired product. Compound No. 390 of Table 14 Using the additional general procedure 2- (2-chloroacetylamino)-4, 5,6, 7-tetrahydro- benzo [b] thiophene-3-carboxylic acid amide (Compound No. 390 of Table 14) was obtained from aminothiophene WO as an off-white solid in 52% yield. m. p. 242-245C (dec.).

The synthetic route of 2-Amino-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxamide has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; SYNGENTA LIMITED; WO2005/44008; (2005); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 54616-47-6, name is 2-Bromo-N,N-dimethylbenzamide, 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 54616-47-6, Recommanded Product: 54616-47-6

General procedure: To a stirred solution of 1 (0.23 g, 1.0 mmol) in THF (6 mL) at -78C was added n-BuLi (1.6 M in hexane; 1.0 mmol) dropwise. After 15 min, PhNCS(0.14 g, 1.0 mmol) was added and stirring was continued for an additional 5 min before addition of saturated aqueous NH4Cl (15 mL). The mixture was extracted with AcOEt (3 ¡Á 10 mL), and the combined extracts were washed with brine (10 mL), dried (Na2SO4) and concentrated by evaporation

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, 2-Bromo-N,N-dimethylbenzamide, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Kobayashi, Kazuhiro; Shigemura, Yuuho; Fujiwara, Daiki; Heterocycles; vol. 94; 6; (2017); p. 1152 – 1158;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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. 402-46-0, name is 4-Fluorobenzenesulfonamide, A new synthetic method of this compound is introduced below., COA of Formula: C6H6FNO2S

100 mg of 4-fluorobenzensulfonamide (0.71 mmol) dissolved with allylamine (434 muL, 5.71 mmol) in a sealed tube was heated at 110 C for 14 days. Then, the mixture was cooled to room temperature and was diluted with MeOH. The solvent was evaporated and the crude mixture was purified by combi-flash with the eluent petroleum ether/ethylacetate: 70/30, thereby obtaining compound 7 (62 mg, 51%) as an orange solid (mp: 74-76 C). 1H NMR (CD3COCD3, 400 MHz, ppm) d: 3.85 (td, CH2, J = 5.5 Hz, J = 1.7 Hz, H10), 5.12 (ddt, 1H, J = 10.3 Hz, J = 1.6 Hz, J = 1.6 Hz, H3′), 5.26 (ddt, 1H, J = 17.2 Hz, J = 1.8 Hz, J = 1.8 Hz, H3′), 5.89 (broad s, 1H, NH), 5.93 (m, CH, H2′), 6.16 (s, SO2NH2), 6.69 (d, 2CH, J = 8.9 Hz, H3 and H5), 7.60 (d, 2CH, J = 8.9 Hz, H2 and H6). 13C NMR (CD3COCD3, 100 MHz, ppm) d: 46.1 (CH2, C1′), 112.2 (2CH, C3 and C5), 116.1 (CH2, C30), 128.7 (2CH, C2 and C6), 131.7 (C1), 136.1 (CH, C2′), 152.5 (C4). MS (IES+, ACN): m/z 213 [M+H]+. HRMS (ESI, CH3OH): m/z 235.0518 (m/z theoretical: 235.05172) [M+Na]+.

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:
Article; Compain, Guillaume; Martin-Mingot, Agnes; Maresca, Alfonso; Thibaudeau, Sebastien; Supuran, Claudiu T.; Bioorganic and Medicinal Chemistry; vol. 21; 6; (2013); p. 1555 – 1563;,
Amide – Wikipedia,
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Electric Literature of 366-49-4, 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 366-49-4 as follows.

To a solution of N-(5-fluoro-2-methylphenyl)acetamide (XXV) (120 g, 717 mmol, 1.0 eq) in HOAc (3 L) was added a solution of Br2 (140 g, 876 mmol, 1.2 eq) in HOAc (1 L) dropwise. The mixture was stirred at 25 C for 3 h. LC/MS showed compound 2 was (XXV) completely consumed. The reaction mixture was quenched with water (8 L). The solid was filtered, washed with water and petroleum ether. The solid was dried in vacuo to give N-(4-bromo-5-fluoro- 2-methylphenyl)acetamide (XXVI) as a white solid (155 g, 629.9 mmol, 87.8% yield). NMR (CDC13, 400 MHz) delta ppm 2.20 (s, 6H), 7.07 (brs, 1H), 7.32 (d, J = 7.2 Hz, 1H), 7.85 (d, J = 10.8 Hz, 1H); ESIMS found C9H9BrFNO mlz 247.2 (M+l).

According to the analysis of related databases, 366-49-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SAMUMED, LLC.; KC, Sunil Kumar; WALLACE, David Mark; CAO, Jianguo; CHIRUTA, Chandramouli; HOOD, John; (265 pag.)WO2017/24010; (2017); A1;,
Amide – Wikipedia,
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Related Products of 1891-90-3, A common heterocyclic compound, 1891-90-3, name is 4-(Trifluoromethyl)benzamide, molecular formula is C8H6F3NO, 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.

First access in the microchannel reactor15 minutes of nitrogen replacement system air,Under full nitrogen protection conditions,Cool down at -30~-25C and start to join.95.5 g (0.5 mol, 99%)P-trifluoromethylbenzamide and 500a mixture of milliliters of methyl tert-butyl ether,At the same time, 0.323 liter (0.55 mol, 1.7 mol/L) was added dropwise.Tert-butyl lithium solution,The reaction solution is all introduced into a cryogenic collector to obtain a compound (III);Compound (III) and 66.1 g (0.6 mol, 99%) were then metered with a metering pump.The methyl methanesulfonate is kept between -30 and -25 C.Finished through the microchannel reactor for 1.5 hours,After the addition, the sample analysis did not detect trifluoromethylbenzamide.The reaction solution is slowly added to the person under nitrogen protection conditions.In ice water between 0-5 C,The solvent is removed by distillation under reduced pressure to give a yellow solid;Nuclear magnetic confirmation as the target product2-Methylsulfonyl-4-trifluoromethylbenzamide.The amount is 132 grams,97.8%,The yield was 96.7%.

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; Papanna (Beijing) Technology Co., Ltd.; Xing Wenlong; Fu Renji; (7 pag.)CN109705005; (2019); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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. 60144-53-8, name is tert-Butyl (4-fluorophenyl)carbamate, A new synthetic method of this compound is introduced below., Formula: C11H14FNO2

(4-Bromo-thiazol-2-yl)-(4-fluoro-phenyl)-carbamic acid tert-butyl ester; A mixture of (4-fluoro-phenyl)-carbamic acid tert-butyl ester (260 mg, 1.23 mmol), 2,4-dibromothiazole (100 mg, 0.41 mmol), copper powder (26 mg, 0.41 mmol), CuCl (41 mg, 0.41 mmol), and KOAc (40 mg, 0.41 mmol) in pyridine (4 ml) is heated at 1000C for 2 hours. The cooled mixture is diluted with EtOAc (30 ml) and washed with H2O (30 ml). The organic layer is dried over Na2SO4, filtered and concentrated in vacuum. The residue is purified by HPLC (C]8 column, eluted with CH3CN/H2O with 0.035% TFA) to give the title compound as solid: 1H NMR (DMSO-d6) delta 1.36 (s, 9H), 7.29 (t, 2H, J = 8.8 Hz), 7.37-7.43 (m, 3H); m/z [M+^t-Bu] 316.9.

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; IRM LLC; WO2007/16228; (2007); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 127828-22-2,Some common heterocyclic compound, 127828-22-2, name is tert-Butyl (2-(2-aminoethoxy)ethyl)carbamate, molecular formula is C9H20N2O3, 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 solution of 2-(2,6-dioxopiperidin-3 -yl)-5-fluoroisoindoline- 1,3 -dione (3-1,100mg, 0.362mmo1, 1 equiv)inNMP(1.8mL, 0.2 M) was added DIPEA (126 jiL, 0.724mmol, 2 equiv) and tert-butyl (2-(2-aminoethoxy)ethyl)carbamate (74 mg, 0.362 mmol, 1 equiv). The reaction mixture was heated to 90 C overnight and then cooled to room temperature. EtOAc (50 mL) was added. The organic layer was washed with water (30 mL) and brine (3 x 30 mL), dried over Na2504, filtered, and concentrated in vacuo. The residue was purified by flashcolumn chromatography on silica gel (eluting with 0 to 5% MeOH in CH2C12) to give the title compound 9-1 as a yellow solid (37 mg, 22%). ?H NIVIR (500 MHz, CDC13) 8.70 (s, 1H), 7.607.47 (m, 1H), 6.99 – 6.85 (m, 1H), 6.74 (d, J= 8.3 Hz, 1H), 5.06 -4.96 (m, 1H), 4.92 (dd, J= 12.0, 5.3 Hz, 1H), 3.72 – 3.63 (m, 2H), 3.58 – 3.48 (m, 2H), 3.33 – 3.24 (m, 4H), 2.95 – 2.66 (m, 3H), 2.09 (ddd, J= 10.5, 6.6, 3.2 Hz, 1H), 1.43 (s, 9H). MS (ESI) [M+H]: 461.2.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route tert-Butyl (2-(2-aminoethoxy)ethyl)carbamate, its application will become more common.

Reference:
Patent; DANA-FARBER CANCER INSTITUTE, INC.; BRADNER, James; BUCKLEY, Dennis; ISHOEY, Mette; WINTER, Georg; (195 pag.)WO2018/98280; (2018); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Related Products of 579474-47-8, 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. 579474-47-8, name is tert-Butyl 2-amino-4-fluorophenylcarbamate, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: 4-(8-Fluoro-2-oxo-2,3-dihydro-1H-benzo[b][1,4]diazepin-4-yl)picolinonitrile (1b). tert-Butyl (2-amino-4-fluorophenyl)carbamate (0.226g, 1mmol) and tert-butyl 3-(2-cyanopyridin-4-yl)-3-oxopropanoate (0.320g, 1.3mmol) were dissolved in toluene (5mL) and heated at reflux for 1h. The reaction mixture was cooled and the excess solvent was removed under reduced pressure. The crude intermediate was taken up in CH2Cl2 and TFA (1.14g, 10mmol) was added dropwise to it at 0C. The resulting reaction mixture was stirred at rt for 7h. The crude mixture was washed with sodium bicarbonate solution and the aqueous layer extracted with CH2Cl2. The combined organic layers were washed with water, then brine, and dried over Na2SO4. Evaporation of the solvent followed by column chromatography using hexanes:ethyl acetate (60:40) yielded the title compound.

The chemical industry reduces the impact on the environment during synthesis tert-Butyl 2-amino-4-fluorophenylcarbamate. I believe this compound will play a more active role in future production and life.

Reference:
Article; Dhanya, Raveendra Panickar; Herath, Ananda; Sheffler, Douglas J.; Cosford, Nicholas D.P.; Tetrahedron; vol. 74; 25; (2018); p. 3165 – 3170;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics