Tag: M.W=100-200

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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121492-06-6, 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. 121492-06-6 name is N-Boc-(2-Aminoethyl)-N-methylamine, 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 l-(benzo[d][l,3]dioxol-5-yl)-3-(4-chloro-6-methylpyrimidin-2-yl)urea (280) (82 mg, 0.27 mmol) and 2-propanol (0.5 mL) was treated with N-(2-aminoethyl)-N- methyl carbamic acid tert-butyl ester (0.06 mL, 0.32 mmol), and triethylamine (0.06 mL, 0.40 mmol) and this was heated to 80 C with stirring overnight. Upon cooling the reaction was diluted with MeOH (3mL) and the precipitate formed was filtered to give the title compound (287) (85 mg, 72%). LC/MS: Method 4: Rt = 2.14 min, m/z = 445.3 [MH+].

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

Reference:
Patent; CURTANA PHARMACEUTICALS, INC.; BEATON, Graham; TUCCI, Fabio C.; RAVULA, Satheesh B.; MCHARDY, Stanton F.; RUIZ, Francisco Xavier, III; LOPEZ, Ambrosio, Jr.; CAMPOS, Bismarck; WANG, Hua-Yu Leo; (241 pag.)WO2016/138479; (2016); A1;,
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711007-44-2, Name is 2,3-Diaminobenzamide, 711007-44-2, belongs to amides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows.

To a solution of 2,3-diamino-benzamide (302 mg, 2 mmol) in ether (12 mL) and DCM(9mL), methyl 2,2,2-trichloroacetimidate (0.44 mL, 2.5 mmol) and TFA (1.0 mL, 12.8 mmol)were added. The reaction mixture was stirred at room temperature for 6 h. After evaporation, andchromatography (DCM/methanol=70:1) gave the title compound 5 as a white solid (340 mg,61.3%).

Statistics shows that 2,3-Diaminobenzamide is playing an increasingly important role. we look forward to future research findings about 711007-44-2.

Reference:
Article; Zhou, Jie; Ji, Ming; Zhu, Zhixiang; Cao, Ran; Chen, Xiaoguang; Xu, Bailing; European Journal of Medicinal Chemistry; vol. 132; (2017); p. 26 – 41;,
Amide – Wikipedia,
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A common heterocyclic compound, 17193-28-1, name is 1-Amino-1-cyclopentanecarboxamide, molecular formula is C6H12N2O, 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. 17193-28-1.

To a solution of 1-aminocyclopentane-l-carboxamide (1.15 g, 8.97 mmol) and DCM (32 mL) was added acetic anhydride (1.191 g, 11.66 mmol). The reaction mixture was stirred at RT for 18 hours. Reaction was concentrated and used without further purification in the next step. Intermediate 110a (1.53 g, 8.99 mmol, 100 % yield). LC-MS (Method A2) RT = 0.43 min, MS (ESI) m/z: 171.1 (M+H)+. 1H NMR (400 MHz, CDCl3) delta 7.09 – 6.89 (m, 1H), 5.72 (br s, 1H), 5.38 – 5.19 (m, 1H), 2.40 – 2.30 (m, 2H), 2.07 – 1.98 (m, 5H), 1.86 – 1.75 (m, 4H)

The synthetic route of 1-Amino-1-cyclopentanecarboxamide has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UNIVERSITE DE MONTREAL; BRISTOL-MYERS SQUIBB COMPANY; PRIESTLEY, Eldon, Scott; REZNIK, Samuel, Kaye; RUEDIGER, Edward, H.; GILLARD, James, R.; HALPERN, Oz, Scott; JIANG, Wen; RICHTER, Jeremy; RUEL, Rejean; TRIPATHY, Sasmita; YANG, Wu; ZHANG, Xiaojun; (642 pag.)WO2018/5591; (2018); A1;,
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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. 1120-16-7 name is Dodecanamide, 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. 1120-16-7

General procedure: For the synthesis of amide carboxylic acid (1-2 mM) wasdissolved in toluene (10 ml) then solution of borane tetrahydrofuran(THF) (1 M) was added at 0 oC. After additionof borane THF complex reaction mixture is kept at roomtemperature for 1 h. DAA was added to the reaction mixtureand reaction mixture refluxed for 5-10 h. Then reactionmixture was cooled to room temperature and acidifies with1M HCl, and extracted with ethyl acetate. Wash with water2-3 times. Organic phase was dried over anhydrous Na2SO4and concentrate under reduced pressure. Purification ofproduct was accomplished by column chromatographyusing silica gel (hexane: ethyl acetate). (+)-N-(dodecanoyl)-dehydroabietylamine (2) Rf: 0.627(hexane/ethylacetate, 9:1) State: gummy, Yield:93.15%, [alpha]D26: -18.42 (C=0.0403, CHCl3), HRMS-ESI:calcd for C32H54NO (M+H)+ 468.4205, found 468.4179,IR (cm-1): 3303 (N-H stretching), 2923 (C-H), 2856(C-H),1647 (C=O), 1548 (N-H bending), 1460 (CH2 bending),1375 (CH3 bending), 719 (CH2 long chain band). UV: lambdamax241, 254, 276. 1HNMR (400MHz, CDCl3) delta ppm: 0.86(3H, t, J = 6.0 Hz, H-12?), 0.98 (3H, s, H-19), 1.23 (24H, Brs, H-16, and 17, 3?-11?), 1.95 (1H, t, J = 5.6 Hz, H-5), 2.32(4H, t, J = 7.6 Hz, H-1, and 2?), 2.86 (2H, m, H-3), 2.98(1H, m, H-15), 3.17 (1H, dd, J = 6.4 and 13.6 Hz, H-18a),3.28 (1H, dd, J = 6.4 and 13.6 Hz, H-18b), 7.28 (1H, d, J =8.0 Hz, H-12), 7.39 (1H, d, J = 8.0 Hz, H-11), 7.83 (1H, s,H-14). 13CNMR (100MHz, CDCl3) delta ppm: 14.1 (C-12?),18.5 (C-2), 18.7 (C-19), 18.9 (C-6), 22.6 (C-11?), 24.7 (C-16 and 17), 25.2 (C-20), 29.5-29.3 (C-3?-9?), 31.8 (C-10?),33.5 (C-15), 33.7 (C-2?), 35.7 (C-3), 37.3 (C-4), 37.4 (C-10), 38.3 (C-1), 44.5 (C-5), 49.7 (C-18), 123.6 (C-12),124.9 (C-11), 132.6 (C-14), 134.7 (C-8), 145.6 (C-13),147.1 (C-9), 173.5 (C-1?).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Dodecanamide, and friends who are interested can also refer to it.

Reference:
Article; Mustufa, Muhammad Ayaz; Aslam, Afshan; Ozen, Cigdem; Ali Hashmi, Imran; Naqvi, Naim ul Hasan; Ozturk, Mehmet; Ali, Firdous Imran; Medicinal Chemistry Research; vol. 26; 7; (2017); p. 1367 – 1376;,
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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 67442-07-3 as follows. 67442-07-3

1. 2-Imidazol-1-yl-N-methoxy-N-methyl-acetamide 60percent sodium hydride in oil (0.296 g, 7.4 mol) was washed with tetrahydrofuran and suspended in additional tetrahydrofuran (10 ml). To this was added imidazole (0.506 g, 7.43 mol) followed by stirring at 25¡ã C. for 1 hour. To the mixture was added a solution of 2-chloro-N-methoxy-N-methyl-acetamide (1.02 g, 7.4 mmol, prepared per Tetrahedron Letters Vol. 30, No. 29, pp3779-80, 1989.) followed by stirring at 25¡ã C. for 15. The mixture was filtered, and the filtrate was evaporated to an oil in vacuo and purifide by chromatography on silica gel eluted with a gradient of chloroform to 10percent methanol:chloroform giving a solid 0.46 g, 37percent yield.

According to the analysis of related databases, 67442-07-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Denny, William Alexander; Hutchings, Richard H; Johnson, Douglas S; Kaltenbronn, James Stanely; Lee, Ho Huat; Leonard, Daniele Marie; Milbank, Jared Bruce John; Repine, Joseph Thomas; Rewcastle, Gordon William; White, Andrew David; US2004/44057; (2004); A1;,
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Amide – an overview | ScienceDirect Topics

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. 630-22-8 name is 2,2-Dimethylpropanethioamide, 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. 630-22-8

N-Bromosuccinimide (107mg, 0.60mmol) was added to a solution of tert-bv yl (3-(2-(2- chloropyrimidin-4-yl)acetyl)-2-fluorophenyl)carbamate (200. Omg, 0.54mmol) in dimethylacetamide (5.5mL). The reaction mixture was stirred at room temperature for lh then 2,2,2-Trimethylthioacetamide (70mg, 0.60mmol) was added. After stirring at room temperature for lh, the medium was heated at 50C overnight. The mixture was poured onto water and the suspension was filtered. The solid was dried under vacuum to afford the title (220mg, 86%). LC/MS (ES+): 463.3-465.3 (M+l).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2,2-Dimethylpropanethioamide, and friends who are interested can also refer to it.

Reference:
Patent; CELLIPSE; PRUDENT, Renaud; PAUBLANT, Fabrice; (74 pag.)WO2018/55097; (2018); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

402-46-0, Adding a certain compound to certain chemical reactions, such as: 402-46-0, name is 4-Fluorobenzenesulfonamide, 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 402-46-0.

General procedure: A solution of compound 9, 12a-12g or 16a-16g (1.0eq),substituted sulfonyl chloride (1.1eq) or substituted acyl chloride(1.1eq) and TEA(1.5eq) were added into DMF(5 ml. And then themixture was stirred at room temperature for 6 h. Upon completion,ethyl acetate (20 ml) and H2O (5 ml) were added. The aqueous layerwas extracted with ethyl acetate for several times, the combinedorganic layers were washed with H2O for several times, and thenwashed with brine, dried over MgSO4 and evaporated to give theproducts. The crude residue was purified by silica gel columnchromatography eluted with a mixture of petroleum ether andethyl acetate (2:1) to obtain target compound.

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; Jian-Song; Gao, Qiu-Lei; Wu, Bo-Wen; Li, Dong; Shi, Lei; Zhu, Ting; Lou, Jian-Feng; Jin, Cheng-Yun; Zhang, Yan-Bing; Zhang, Sai-Yang; Liu, Hong-Min; European Journal of Medicinal Chemistry; vol. 183; (2019);,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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. 1520-70-3 name is Ethanesulfonamide, 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. 1520-70-3

EXAMPLE 154 N-(4-fluorobenzyl)-8-hydroxy-5-[methyl(methylsulfonyl)amino]-1,6-naphthyridine-7-carboxamide To a mixture of methyl-methanesulfonamide (1.06 g, 9.65 mmol), 5-bromo-N-(4-fluorobenzyl)-8-hydroxy-1,6-naphthyridine-7-carboxamide (1.21 g, 3.22 mmol), and Cu2O (0.46 g, 3.22 mmol) under an atmosphere of argon was added pyridine (25 mL) and the suspension was stirred at reflux for 16 hr. The reaction was allowed to cool to room temperature and the solvent evaporated in vacuo. The residue was treated with DMF (12 mL) and TFA (0.5 mL) and filtered to remove the solids. The filtrate was purified by reverse phase HPLC. (Waters PrePak 500 cartridge C18, Gradient elution with Water: Acetonitrile 95:5 to 5:95 with 0.1percent TFA at 75 mL/min over 45 mins). Lyophilization of the pure fractions afforded the title compound as an off white solid. 1H NMR (d6DMSO, 400 MHz) delta 13.80 (1H, s), 9.66 (1H, t, J=6.4 Hz), 9.19 (1H, d, J=4.2 Hz), 8.62 (1H, d, J=8.4 Hz), 7.88 (1H, dd, J=8.4 and 4.2 Hz), 7.41 (2H, dd, J=8.6 and 5.7 Hz), 7.18 (2H, t, J=8.9 Hz), 4.61 (2H, d, J=6.4 Hz) 3.38 (3H, s), 3.19 (3H, s) ppm. FAB MS calcd for C18H17FN4O4S 405 (MH+), found 405.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Ethanesulfonamide, and friends who are interested can also refer to it.

Reference:
Patent; Anthony, Neville J.; Gomez, Robert P.; Young, Steven D.; Egbertson, Melissa; Wai, John S.; Zhuang, Linghang; Embrey, Mark; Tran, LeKhanh; Melamed, Jeffrey Y.; Langford, H. Marie; Guare, James P.; Fisher, Thorsten E.; Jolly, Samson M.; Kuo, Michelle S.; Perlow, Debra S.; Bennett, Jennifer J.; Funk, Timothy W.; US2003/55071; (2003); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

These common heterocyclic compound, 4664-01-1, name is 3,4-Pyridinedicarboximide, 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. 4664-01-1

Preparation 18 3-Aminopyridine-4-carboxylic acid To an ice cold mixture of 3,4-pyridinedicarboximide (5.2 g, 35.11 mmol) in 10% sodium hydroxide (85 mL) was added bromine (1.84 mL, 35.8 mmol), dropwise. The resulting solution was heated to 80 C. for 1 hour, cooled on ice, and the acidity was carefully adjusted to pH 5.5 with acetic acid. The precipitate was collected, washed well with water and air dried to afford 3-aminopyridine-4-carboxylic acid (2.74 g, 57%). 1H NMR (DMSO d6) delta8.20 (s,1 H), 7.72 (d, J=5 Hz, 1 H), 7.45 (d, J=5 Hz, 1 H). The material was used without purification.

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 4664-01-1.

Reference:
Patent; Pfizer Inc; US6323208; (2001); B1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics