Author: Jessica.F

Electric Literature of 90-16-4, These common heterocyclic compound, 90-16-4, name is Benzo[d][1,2,3]triazin-4(3H)-one, 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 solution of l,2,3-benzotriazin-4(3H)-one (commercially available, 1.0 equiv.), 2- chloromethyl-oxirane (4.0 equiv.) and potassium carbonate (4.0 equiv.) in methyl ethyl ketone was refluxed for about 16 hours. The reaction mixture was concentrated under vacuum; the residue was taken in water and extracted with ethyl acetate. The organic layer was washed with water, dried and concentrated. The residue was purified by silica gel column chromatography using mixture of ethyl acetate and hexane as eluent to form 3- (oxiran-2-ylmethyl)-l,2,3-benzotriazin-4(3H)-one. Yield: 75%

The synthetic route of 90-16-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RANBAXY LABORATORIES LIMITED; WO2006/117760; (2006); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 112257-19-9, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 112257-19-9 name is tert-Butyl methyl(2-(methylamino)ethyl)carbamate, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Step 6 tert-Butyl (2-(((3-iodo-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-4-yl)methyl)(methyl)amino)ethyl)(methyl)carbamate A mixture of 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*300 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]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, tert-Butyl methyl(2-(methylamino)ethyl)carbamate, and friends who are interested can also refer to it.

Reference:
Patent; Epizyme, Inc.; Mitchell, Lorna Helen; Shapiro, Gideon; Chesworth, Richard; Moradei, Oscar Miguel; US2014/288128; (2014); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 224789-21-3, 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 224789-21-3 as follows.

Example 5 Preparation of 2-(2-ethoxy-5-chlorosulfonyl)-phenyl-5-methyl-7-n-propyl-3H-imidazolo[5,1-f][ 1,2,4]triazine-4-one Chlorosulfuric acid (50ml)was added into a 100ml three-neck flask with a stirrer, 2-(2-ethoxy)-phenyl-5-methyl-7-n-propyl-3H-imidazolo[5,1-f][1,2,4]triazine-4-one (31.2g (0.1mol))was added in batches under stirring in an ice bath. The reaction was exothermic and was performed for 12 hrs. The reaction solution was slowly poured into icy water (100g), a white solid was separated out, filtered, dried. A white solid (30g)was obtained with a yield of 76%.

According to the analysis of related databases, 224789-21-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Zhejiang Dade Pharmaceutical Group Co., Ltd.; WANG, Jianping; WANG, Jianguo; EP2666776; (2013); A1;,
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 402-46-0 as follows. name: 4-Fluorobenzenesulfonamide

General procedure: To a round-bottom flask (500 mL) that contained a solution of aryl sulfonamide (6 mmol), 4-dimethyaminopyridine (DMAP, 13 mmol), and 1-[3-(dimethyamino)-propyl]-3-ethylcarbodiimide hydrochloride (EDCI, 13 mmol) in CH2Cl2 (150 mL) was added the synthesized cinnamic acid (6 mmol) at room temperature. The resulting mixture was stirred at room temperature for 12 h, then cooled to 5 C, 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 (9a-16e) (Scheme 1).

According to the analysis of related databases, 402-46-0, the application of this compound in the production field has become more and more popular.

Reference:
Article; Luo, Yin; Qiu, Ke-Ming; Lu, Xiang; Liu, Kai; Fu, Jie; Zhu, Hai-Liang; Bioorganic and Medicinal Chemistry; vol. 19; 16; (2011); p. 4730 – 4738;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 32428-71-0, name is 2-Chloro-N-(2-ethyl-6-methylphenyl)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 32428-71-0, Formula: C11H14ClNO

A. 1-[(2-Ethyl-6-methylphenyl)carbamoylmethyl]-2-methyl-2-imidazoline. In a manner similar to Ex. IA react 21.17 gm. (0.1 M) of 2-chloro-2′-ethyl-6′-methylacetanilide and 42.1 gm. (0.5 M) of lysidine in 250 ml. of nitromethane, to obtain the title compound: NMR (CDCl3): delta=1.16(t,3), 1.97(s,3), 2.18(s,3), 2.54 (q,2), 3.10-3.70(m,4), 3.87(s,2), 7.15 (s,3) and 8.78(bs,1)ppm.

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; Berlex Laboratories, Inc.; US4353921; (1982); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Some common heterocyclic compound, 147751-16-4, name is tert-Butyl methylsulfonylcarbamate, molecular formula is C6H13NO4S, 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. Recommanded Product: tert-Butyl methylsulfonylcarbamate

Example 243: t-ButylN-[4-[(4-chlorophenyl)sulfonyl]-4-(2,5-difluorophenyl)-3-methylbutyl]-N-methylsulfonylcarbamate The 4-[(4-chlorophenyl)sulfonyl]-4-(2,5-difluorophenyl)-3-methyl-1-butanol (97.2 mg, 0.259 mmol) obtained in Example 239, t-butyl N-methylsulfonylcarbamate (101 mg, 0.518 mmol) and triphenylphosphine (138 mg, 0.518 mmol) were dissolved in tetrahydrofuran (3 ml), followed by the addition of diisoopropyl azodicarboxylate (102 mul, 0.518 mmol) at room temperature.. The reaction mixture was stirred at room temperature for 18 hours.. The reaction mixture was diluted with ethyl acetate, washed with a saturated aqueous solution of ammonium chloride, water and brine, dried over magnesium sulfate and then concenetrated.. The residue thus obtained was subjected to flash chromatography on a silica gel column, and the fraction obtained from the hexane:ethyl acetate=3:2 elude was concentrated, whereby the title compound (136 mg, 0.246 mmol, 95%) was obtained as a colorless amorphous substance.1H-NMR (400 MHz, CDCl3) delta: 1.33(3H,d,J=6.8Hz), 1.35-1.45(1H,m), 1.52(9H,s), 1.99-2.08(1H,m), 2.70-2.78(1H,m), 3.27(3H,s), 3.65-3.76(2H,m), 4.45(1H,d,J=7.6Hz), 6.77(1H,td,J=9.0,4.6Hz), 6.91-6.97(1H,m), 7.32(2H,d,J=8.5Hz), 7.38-7.45(1H,m), 7.50(2H,d,J=8.5Hz). MS m/z: 552 (M++H), 574 (M++Na). FAB-MS: 552.1070 (Calcd for C23H29ClF2NO6S2: 552.1093), 574.0875 (Calcd for C23H28ClF2NO6S2Na: 574.0912).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 147751-16-4, its application will become more common.

Reference:
Patent; DAIICHI PHARMACEUTICAL CO., LTD.; EP1466898; (2004); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 87905-98-4, name is Benzyl (5-hydroxypentyl)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 87905-98-4, category: amides-buliding-blocks

To a solution of oxalyl chloride (814 mul, 9.62 mmol, 2.3 equiv.) in dried dichloromethane (25 ml) under an inert atmosphere was slowly added a solution of dimethylsulfoxyde (1.3 ml, 18.2 mmol, 4.3 equiv.) in dried dichloromethane (10 ml). The solution was stirred for 5 min at -70C then a suspension of benzyl ((5-hydroxypentyl)carbamate) [21] (1 g, 4.22 mmol, 1 equiv.) in dried dichloromethane (25 ml) was transferred via canula. The mixture was stirred for 25 min at -70C then triethylamine (11.7 ml, 8.44 mmol, 20 equiv.) was slowly added. The reaction mixture was stirred for 20 min at -70C and 15 min at room temperature and then quenched by addition to 600 ml of water. The aqueous phase was extracted with diethylether (3×100 ml) and the combined organic layers were dried over magnesium sulfate, filtered and concentrated to dryness under reduced pressure to obtain the aldehyde (1.1 g) used in the next step without purification. To a suspension of potassium cyanide (249 mg, 3.83 mmol, 1 equiv.) in water (520 mul) were added ammonium chloride (203 mg, 3.83 mmol, 1 equiv.) and ammonium hydroxide 33% (1.32 ml; 20.3 mmol, 5.3 equiv.). The reaction mixture was stirred for 15 min at 0C then a solution of the aldehyde (900 mg, 3.83 mmol, 1 equiv.) in dioxane (1.35 ml) was added dropwise over 20 min. The mixture was stirred for 20 h and then quenched by addition of water (10 ml) and diethyl ether (30 ml). The aqueous phase was acidified with HCl 1 M (50 ml), washed with diethyl ether (3×20 ml), basified to pH = 12 with NaOH 1 M (20 ml) and then extracted with dichloromethane (4×10 ml). The combined organic layers were dried over magnesium sulfate, filtered and concentrated to dryness under reduced pressure to obtain the protected aminonitrile; yield: 905 mg (91%). 1H NMR (MeOD-d4, 300 MHz) delta 1.52 (m, 4H, H4, H5), 1.71 (m, 2H, H3), 3.14 (t, 2H, H6), 3.71 (t, 2H,H2), 5.06 (s, 2H, H8), 7.34 (m, 5H, H10-H12); 13C NMR (MeOD-d4, 75 MHz) . 23.9 (C4), 30.4 (C5), 35.9 (C3), 41.5 (C6), 44.2 (C2), 67.4(C8), 123.1 (C1), 128.8-129.6 (C10-C12), 138.6 (C9), 159.0 (C7) (seeSI, Figs. S3 and S4).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Benzyl (5-hydroxypentyl)carbamate, and friends who are interested can also refer to it.

Reference:
Article; Bordier, Franck; Stam, Mark; Darii, Ekaterina; Tricot, Sabine; Fossey, Aurelie; Rohault, Johanna; Debard, Adrien; Mariage, Aline; Pellouin, Virginie; Petit, Jean-Louis; Perret, Alain; Vallenet, David; Salanoubat, Marcel; Weissenbach, Jean; Vergne-Vaxelaire, Carine; De Berardinis, Veronique; Zaparucha, Anne; Journal of Molecular Catalysis B: Enzymatic; vol. 107; (2014); p. 79 – 88;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 72505-21-6, 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. 72505-21-6, name is 4-(Trifluoromethyl)thiobenzamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: Appropriate thiobenzamides or thioacetamides (1 mmol) and alpha-chloroacetoacetate 3 (150 mg, 1.2 mmol) were added to absolute ethanol (15 mL). The reaction mixture was heated at reflux for 24 h. After removal of solvent under reduced pressure, the residue was purified by silica gel chromatography using hexanes-ethyl acetate (7:3) to provide the desired compounds.

The synthetic route of 4-(Trifluoromethyl)thiobenzamide has been constantly updated, and we look forward to future research findings.

Reference:
Article; Mayhoub, Abdelrahman S.; Khaliq, Mansoora; Botting, Carolyn; Li, Ze; Kuhn, Richard J.; Cushman, Mark; Bioorganic and Medicinal Chemistry; vol. 19; 12; (2011); p. 3845 – 3854;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 51-06-9, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 51-06-9 name is 4-Amino-N-(2-diethylaminoethyl)benzamide, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

A mixture of p-SCN-Bn-NOTA (0.05 g, 0.09 mmol) and 4-amino-N-(2-(diethylamino)ethyl)benzamide (0.030 g, 0.11 mmol) in CHCl3 (1 mL) containing TEA (45 muL, 0.27 mmol) was stirred 24 h at room temperature. The solvent was evaporated under reduced pressure. The resulting product was purified by semi-preparative HPLC (gradient 10% of H2O for 5 min and 10-70% of MeCN for 30 min; flow rate, 2 mL/min; 240 nm; tR, 12 min) to give SCN-NOTA-BZA as a pale yellow solid (46 mg, 75%). MS (FAB) m/z 686, (M+H)+; HRMS of C33H48N7O7S 686.3336 (calculated) and 686.3340 (observed); 1H NMR (500 MHz, D2O): delta 7.68 (d, 1H), 7.34 (d, 2H), 7.20 (m, 4H), 3.67-3.65 (br, 2H), 3.54-3.50 (br, 2H), 3.39-3.29 (br, 4H), 3.20-3.12 (br, 6H), 3.09-2.99 (br, 8H), 2.92-2.52 (br, 3H), 1.20-1.14 (br, 8H); 13C NMR (125 MHz, D2O): delta 179.3, 178.5, 176.3, 174.4, 169.8, 142.0, 136.8, 136.1, 130.3, 130.0, 129.8, 128.8, 128.2, 126.0, 125.6, 124.5. 60.6, 57.8, 57.6, 57.2, 57.1, 52.4, 52.1, 51.6, 50.6, 47.6, 46.6, 46.0, 43.5, 34.9, 33.7, 33.6, 8.2, 8.1.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Amino-N-(2-diethylaminoethyl)benzamide, and friends who are interested can also refer to it.

Reference:
Article; Kim, Hee-Jung; Kim, Dong-Yeon; Park, Jeong-Hoon; Yang, Seung-Dae; Hur, Min-Goo; Min, Jung-Joon; Yu, Kook-Hyun; Bioorganic and Medicinal Chemistry; vol. 20; 16; (2012); p. 4915 – 4920;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Related Products of 7150-72-3, A common heterocyclic compound, 7150-72-3, name is tert-Butyl vinylcarbamate, molecular formula is C7H13NO2, 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: A 10 mL round-bottomed flask equipped with a rubber septum and a magnetic stir bar was charged with 1 (1.0 equiv), 2 (2.5 equiv), 3 (2.0 equiv), and fac-Ir(ppy)3 (0.01 equiv). The flask was evacuated and backfilled 3 times with N2. DMSO was then added with syringe under N2. The mixture was then irradiated by white LED strips. After completion of the reaction (6 h, as judged by TLC analysis), the mixture was poured into a separatory funnel containing sat. aq NaHCO3 (20mL) and EtOAc (20 mL). After extraction with EtOAc, the organic layer was separated, dried (Na2SO4), and concentrated under reduced pressure after filtration. The crude product was purified by flash chromatography on silica gel to afford the desired product 4.

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; An, Xiao-De; Yu, Shouyun; Synthesis; vol. 50; 17; (2018); p. 3387 – 3394;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics