Author: tianli

A common heterocyclic compound, 239074-29-4, name is tert-Butyl (trans-4-(hydroxymethyl)cyclohexyl)carbamate, molecular formula is C12H23NO3, 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. 239074-29-4.

A suspension of 7-chloro-8-hydroxy-l-methyl-l,5-naphthyridin-2(lH)-one (1 g, 4.75 mmol) (for a synthesis see WO2008006648 Example l(c)) in THF (24 ml) was stirred at rt and treated with 1,1-dimethylethyl [trans-4-(hydroxymethyl)cyclohexyl]carbamate (1.089 g, 4.75 mmol, for a preparation see Example l(g)), triphenylphosphine (1.619 g, 6.17 mmol) and DIAD (1.215 ml, 6.17 mmol). The resulting yellow suspension was stirred for 30 min then heated at 8O0C for 3.5 hours. Additional triphenylphosphine (0.8 g, 3.05 mmol) and DIAD (0.6 ml, 3.05 mmol) were added and the suspension (now orange) was heated to 8O0C for 2 hours. The suspension was cooled and stirred at rt overnight. The solvent was evaporated under vacuum and to deliver an orange gum. Chromatography on silica, eluting with 0-50% DCM/CH3CN gave a white solid that contained residual triphenylphosphine oxide. Diethylether (50 mL) was added and the resulting suspension was stirred for 30 minutes, filtered under vacuum. The precipitate was dissolved in DCM, filtered and the filtrate was evaporated to give the title compound (1.16 g, 42%). MS (ES+) m/z 422 [MH+].

The synthetic route of tert-Butyl (trans-4-(hydroxymethyl)cyclohexyl)carbamate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; JONES, Graham, Elgin; MARKWELL, Roger, Edward; HENNESSY, Alan Joseph; MILES, Timothy; PEARSON, Neil David; WO2010/45987; (2010); A1;,
Amide – Wikipedia,
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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. 3144-09-0, name is Methylsulfonamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 3144-09-0

e) Boc-N-(4-Benzylsulfanyl-5-nitro-thiophen-3-ylmethyl)-methanesulfonamide Triethylamine (22.0 mL, 158 mmol), di-tert-butyl dicarbonate (27.5 g, 126 mmol), and 4-(N,N-dimethylamino)pyridine (1.28 g, 10.5 mmol) were added sequentially to a solution of methanesulfonamide (10.0 g, 105 mmol) in dichloromethane (300 mL) at 25 C. The mixture was stirred at 25 C. for 2 h, and then was concentrated in vacuo to ~40 mL volume. Ethyl acetate (350 mL) was added and the mixture was washed with 1.0 M aqueous hydrochloric acid solution (300 mL). The aqueous layer was extracted with ethyl acetate (250 mL) and the combined organic layers were dried over sodium sulfate, filtered and were concentrated in vacuo to afford Boc-N-methanesulfonamide (17.1 g, 87.6 mmol, 83%) as a white solid. 1H NMR (400 MHz, CDCl3) delta: 1.53 (9H, s), 3.27 (3H, s).

The synthetic route of 3144-09-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Anadys Pharmaceuticals, Inc.; US2009/306057; (2009); A1;,
Amide – Wikipedia,
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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. 6973-09-7 name is 5-Amino-2-methylbenzenesulfonamide, 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. 6973-09-7

Example 69 5-({4-[(2,3-dimethyl-2H-indazol-6-yl)(methyl)amino]pyrimidin-2-yl}amino)-2-methylbenzenesulfonamide To a solution of Intermediate Example 13 (200 mg, 0.695 mmol) and 5-amino-2-methylbenzenesulfonamide (129.4 mg, 0.695 mmol) in isopropanol (6 ml) was added 4 drops of conc. HCl. The mixture was heated to reflux overnight. The mixture was cooled to rt and diluted with ether (6 ml). Precipitate was collected via filtration and washed with ether. HCl salt of 5-({4-[(2,3-dimethyl-2H-indazol-6-yl)(methyl)amino]-pyrimidin-2-yl}amino)-2-methylbenzenesulfonamide was isolated as an off-white solid. 1H NMR (400 MHz, d6DMSO+NaHCO3) delta 9.50 (br s, 1H), 8.55 (br s, 1H), 7.81 (d, J = 6.2 Hz, 1H), 7.75 (d, J = 8.7 Hz, 1H), 7.69 (m, 1H), 7.43 (s, 1H), 7.23 (s, 2H), 7.15 (d, J = 8.4 Hz, 1H), 6.86 (m, 1H), 5.74 (d, J = 6.1 Hz, 1H), 4.04 (s, 3H), 3.48 (s, 3H), 2.61 (s, 3H), 2.48 (s, 3H). MS (ES+, m/z) 438 (M+H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Amino-2-methylbenzenesulfonamide, and friends who are interested can also refer to it.

Reference:
Patent; Novartis AG; Boloor, Amogh; Cheung, Mui; Davis, Ronda; Harris, Philip Anthony; Hinkle, Kevin; Mook, Robert Anthony Jr; Stafford, Jeffery Alan; Veal, James Martin; EP2311825; (2015); B1;,
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A common heterocyclic compound, 6331-71-1, name is 4-Amino-N,N-dimethylbenzamide, molecular formula is C9H12N2O, 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. 6331-71-1.

A solution of 26.4 g of 4-amino-N,N-dimethylbenzamide in 500 ml toluene and 60 g acetonylacetone is refluxed for 16 hours under a Dean-Stark water separator. The solution is washed with water and brine, dried over MgSO4, filtered and the solvent evaporated at 60 and reduced pressure. The residue is crystallized from ether-hexane 1:1 to yield 1-(4-dimethylcarbamoylphenyl)-2,5-dimethyl-1H-pyrrole, m.p. 102-104.

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

Reference:
Patent; Ciba-Geigy Corporation; US4960787; (1990); A;,
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108468-00-4,Some common heterocyclic compound, 108468-00-4, name is 1-(N-Boc-aminomethyl)-4-(aminomethyl)benzene, molecular formula is C13H20N2O2, 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 solution of 4-(Boc-aminomethyl)benzylamine (1) (1.0 mmol)and TEA (3.0 mmol) in anhydrous DCM (8 mL) was cooled with anice bath, then the corresponding sulfochloride (1.1 mmol, dissolvedin 2mL anhydrous DCM) was added dropwise. The reactionmixture was allowed to stir at 0 C for 1 h. After removing thecooling bath, the resulting mixture was stirred for 5 h at roomtemperature, then diluted with saturated aqueous NaHCO3 andextracted with DCM (10 mL) for three times. The combined organiclayer was sequentially washed with water and brine, dried withanhydrous Na2SO4, and concentrated in vacuo. The crude was purifiedby column chromatography with DCM/methanol (150:1, v/v)to yield the product as a white solid [5].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 108468-00-4, its application will become more common.

Reference:
Article; Bai, Renren; Sun, Jian; Liang, Zhongxing; Yoon, Younghyoun; Salgado, Eric; Feng, Amber; Oum, Yoonhyeun; Xie, Yuanyuan; Shim, Hyunsuk; European Journal of Medicinal Chemistry; vol. 150; (2018); p. 195 – 205;,
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2675-89-0, A common compound: 2675-89-0, name is 2-Chloro-N,N-dimethylacetamide, belongs to amides-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

EXAMPLE 18; N,N-Dimethylaminocarbonylmethyl 3-Aminosulfonyl-5-butylamino-4- phenoxybenzoate (Bumetanide N,N-Dimethylglycolamido Ester); [0481] Bumetanide (1.2g, 3.29 mmol) was dissolved in dimethylformamide (DMF, 10 mL) and 2- chloro-N,N-dimethylacetamide (410 muL, 3.9 mmol) was added followed by triethylamine (0.70 mL) and sodium iodide (545 mg, 3.6 mmol). The reaction was heated to 50C for 10 hours, TLC and LC/MS indicated the reaction was complete. The solvent was removed under reduced pressure and the residue was dissolved in ethyl acetate and washed with saturated sodium bicarbonate, water, and brine and dried over anhydrous magnesium sulfate. The ethyl acetate was removed under reduced pressure and the product was purified via flash chromatography on silica gel to yield 685 mg (60%) of pure N,N- dimethylaminocarbonylmethyl 3-aminosulfonyl-5-butylamino-4-phenoxybenzoate.

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-Chloro-N,N-dimethylacetamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NEUROTHERAPEUTICS PHARMA, INC.; WANAKSI, Stephen; PARTRIDGE, John, J.; COLLINS, Stephen; WO2010/85352; (2010); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

102-93-2, 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. 102-93-2 name is 3-Phenylpropanamide, 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.

DCM (20 mL) was added to a flask containing Lawesson?s reagent (2.022 g, 5.00 mmol). 3-Phenylpropanamide (1 .492 g, 10.00 mmol) was dissolved in DCM (20 mL), added tothe suspension, and stirred at room temperature for 16 hours. The mixture was concentrated under reduced pressure and purified by column chromatography (DCM) to afford the title compound (1 .07 g 1H NMR (500 MHz, ODd3) O 7.30 (t, 2H), 7.24 – 7.21 (m, 3H), 3.12 (t, 2H), 2.95 (t, 2H)

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Phenylpropanamide, and friends who are interested can also refer to it.

Reference:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; BLUM, Francesca; CARR, James Lindsay; SHAH, Pritom; DEL MAR JIMENEZ QUESADA, Maria; FARRE GUTIERREZ, Irene; (213 pag.)WO2016/124938; (2016); A1;,
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Some common heterocyclic compound, 609-66-5, name is 2-Chlorobenzamide, molecular formula is C7H6ClNO, 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. 609-66-5

General procedure: (Diacetoxyiodo) benzene (5 mmol, 1.61g) and NaHSO4.H2O (1mmol, 0.138g) were stirred for 10-15 min, at room temperature in aqueous solution of acetonitrile (5 ml water and 5 mlacetonitrile). In this reaction mixture benzamide (1mmol) was added and stirring was continuing till reaction goes to completion (TLC). After completion of reaction, the reaction mixture was quenched with water and further extracted with chloroform (3¡Á10 ml). The combined chloroform layers were washed with water (3¡Á20ml) dried over Na2SO4, and concentrated on rota-evaporator to get the crude residue. The residue was further purified by column chromatography on silica gel using ethyl acetate: hexane (1:9) as an eluent to afford pure benzoquinone.

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

Reference:
Article; Sasane, Kulbhushan A.; Telvekar, Vikas N.; Synthetic Communications; vol. 44; 4; (2014); p. 468 – 473;,
Amide – Wikipedia,
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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 3984-14-3 as follows. 3984-14-3

Step 16: Synthesis of N-[17-[2-(3-isopropylpyrazo]-l-yl)-7-methoxy-8-methylquinolin- 4-yloxy]-13-methyl-2,14-dioxo-3,13-diazatricyclo[13.3.0.Cf’6]octadec-7-ene-4- carbonyl](dimethylamino)sulfonamide (29).; A mixture of 27 (181 mg, 0.29 mmol) and CDI (117 mg, 0.72 mmol) in dry THF (15 mL) was heated at reflux under nitrogen for 50 min. LCMS analysis showed one peak of the intermediate 28, which if needed, can be isolated by column chromatography or can be reacted with the appropriate sulfonamide in a one- pot reaction. The reaction mixture was cooled down to room temperature and dimethylaminosulfonamide (98 mg, 0.79 mmol) was added. Then, DBU (141 mg, 0.92 mmol) was added and the reaction mixture was heated to 550C. After 12 h, the solvent was evaporated, and the residue partitioned between AcOEt and acidic water (pH = 4). The organic layer was EPO dried (Na2SO4) and evaporated under reduced pressure to give a crude material, which was purified by column chromatography (AcOEtZCH2Cb, 25:75) to give 70 mg (33 %) of the target compound 29 as a white powder: m/z = 736 (M+H)+. 1H NMR (CDCl3): 1.20-1.50 (m, 10H), 1.60- 1.75 (m, IH), 1.79-1.91 (m, 2H), 1.92-2.03 (m, IH), 2.19-2.48 (m, 3H), 2.52-2.63 (m, 5H), 2.89-2.96 (m, 7H), 3.03 (s, 3H), 3.04-3.14 (m, IH), 3.35-3.42 (m, 2H), 3.97 (s, 3H), 4.60 (dt, J = 13.2 Hz, J = 2.2 Hz, IH), 5.05 (t, / = 10.4 Hz, IH), 5.26-3.35 (m, IH), 5.64-5.70 (m, IH), 6.26 (s, IH), 6.32 (d, J = 2.5 Hz, IH), 7.11-7.15 (m, IH), 7.30 (s, IH), 7.95 (d, / = 9.1 Hz, IH), 8.69 (d, / = 2.5 Hz, IH), 10.6 (br s, IH).

According to the analysis of related databases, 3984-14-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TIBOTEC PHARMACEUTICALS LTD.; MEDIVIR AB; WO2007/14925; (2007); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Some common heterocyclic compound, 116091-63-5, name is 2-Methoxy-5-(2-oxopropyl)benzenesulfonamide, molecular formula is C10H13NO4S, 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. 116091-63-5

Preparation of R,R-2-Methoxy-5-[2-(1-phenylethylamino)-propyl]benzenesulfonamide, hydrochloride (Formula IV) (3-sulfonamido-4-methoxyphenyl)-2-propanone obtained from Example 1 was added to methanol (300 ml) and activated Raney Ni (1.5 g) in a hydrogenation flask. R(+)-1-phenyl ethylamine (1 g) was added and hydrogen gas was applied at a pressure of 3.5 bar. Temperature was raised to 50 C. and pressure raised to 5.5. bar. The reaction mixture was cooled to room temperature and Raney Ni filtered through hyflo bed. The filtrate was concentrate under reduced pressure at 50 C. and toluene (10 ml) was added. The resultant solution was concentrated at 50-60 C. under reduced pressure to recover toluene completely and get a thick oil (3 g approx.) of the title compound.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 116091-63-5, its application will become more common.

Reference:
Patent; Ranbaxy Laboratory Limited; US6894188; (2005); B1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics