Month: March 2021

Related Products of 1172623-95-8,Some common heterocyclic compound, 1172623-95-8, name is tert-Butyl (1-(methoxy(methyl)amino)-1-oxopent-4-yn-2-yl)carbamate, molecular formula is C12H20N2O4, 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.

Under N2 protection, 2,5-difluorobromobenzene (15.05 g, 78 mmol) was dissolved in dry toluene (50 ml), cooledto -10C or lower in an ice salt bath, and a solution of isopropyl magnesium chloride/lithium chloride in tetrahydrofuran(66 ml, 1.3 mol/l) was added dropwise, followed by stirring at about -10C for 1 hour. 1D (10 g, 39 mmol) was dissolvedin dry tetrahydrofuran (100 ml), and added dropwise to the reaction solution while the temperature was maintained at-10C. When the addition was complete, the reaction was allowed to proceed at room temperature for 4 hours. Thetemperature was lowered to about -10C, and a saturated ammonium chloride solution (40 ml) was added dropwise,followed by stirring for 10 min. The pH was adjusted to 5 to 6 with a 3 mol/l hydrochloric acid solution, to allow settlingand partitioning. The aqueous phase was extracted with methyl t-butyl ether (50 ml32). The organic phases werecombined, washed with a saturated sodium chloride solution (30 ml32), dried by addition of anhydrous sodium sulfatethereto, filtered, concentrated, and separated by column chromatography (petroleum ether/ethyl acetate (v/v) = 50:1 to8:1), to obtain a light yellow solid 1E (10.1 g, yield 83.5%).MS m/z (ESI): 210.1 [M-99].

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 (1-(methoxy(methyl)amino)-1-oxopent-4-yn-2-yl)carbamate, its application will become more common.

Reference:
Patent; Sichuan Haisco Pharmaceutical Co., Ltd.; ZHANG, Chen; WANG, Jianmin; LI, Caihu; WEI, Yonggang; (64 pag.)EP3159344; (2017); A1;,
Amide – Wikipedia,
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Synthetic Route of 104060-23-3, A common heterocyclic compound, 104060-23-3, name is N-Boc-2-(4-Aminophenyl)ethanol, molecular formula is C13H19NO3, 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.

Compound 11A (2.5 g, 10.5 mmol, 1.00 equiv) was dissolved in 25 mL of DCM then cooled to -78C. A Dess-Martin Periodinane solution (DMP, 6.71 g, 15.8 mmol, 1.5 equiv) in DCM (10 mL) was added drop-wise. The cold bath was removed and agitation continued for 1 hour at ambient temperature. The reaction was neutralised with60 mL of a 50/50 mixture of sodium bicarbonate-saturated aqueous solution and Na2S2O3-saturated aqueous solution. The resulting solution was extracted 3 times with 30 mL of EtOAc. The organic phases were combined, washed twice with NaC1- saturated aqueous solution, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified on silica gel (EtOAc/PE1/15) to yield 1.0 g (40 %) of compound 11B in the form of a pale yellow solid.

The synthetic route of 104060-23-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PIERRE FABRE MEDICAMENT; PEREZ, Michel; RILATT, Ian; LAMOTHE, Marie; WO2014/174060; (2014); A1;,
Amide – Wikipedia,
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Electric Literature of 53250-82-1, 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. 53250-82-1, name is 4-(Methylsulfonamido)aniline belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Take a 250mL three-necked bottle, add 1.86g of p-methylsulfonylaminoaniline, 0.22g of palladium acetate and 1.00g of molecular sieve.2.04 g of methyl 2-oxopropanoate, 0.60 g of acetic acid and 100 mL of dimethyl sulfoxide were injected, followed by a 200 mL oxygen balloon, and stirred at 70 C for 18 hours.After the reaction was completed, 200 mL of ethyl acetate was added to dilute the reaction solution, and the filtered saline 100 mL was washed twice.The organic phase was separated and the aqueous phase was extracted 1time with ethyl acetate.Column chromatography yielded 2.15 g of pure methyl 5-methanesulfonylamino-1H-indole-2-carboxylate in a yield of 80%.

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

Reference:
Patent; Chinese Academy Of Medical Sciences Pharmaceutical Institute; Xiao Zhiyan; Ren Long; Tang Yanbo; Yang Ying; (27 pag.)CN109748840; (2019); A;,
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. 85006-25-3, name is tert-Butyl (tert-butoxycarbonyl)oxycarbamate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Product Details of 85006-25-3

To a suspension of sodium hydride (60% in mineral oil, 10 mg, 0.250 mmol) in 0.5 mL of DMF , N,O-diBoc-hydroxylamine (55.6 mg, 0.230 mmol) was added. The mixture was stirred for 30′ at 0C then a solution of 3-[3′- Adamantan-1 -yl-4′-(2-bromo-ethoxy)-biphenyl-4-yl]-acrylic acid ferf-butyl ester (103 mg, 0.192 mmol) in 2 mL of DMF was slowly added. After having stirred at room temperature overnight, DMF was evaporated, the residue was poured into saturated solution of NH4CI and extracted with ethyl acetate. The organic phase was dried and evaporated. Purification by flash chromatography (Hexane/Ethyl acetate 90:10) gave 109 mg (81 %) of the desired compound as white solid; m.p. 165C, Rf(Hexane/Ethyl acetate 90:10) 0.26.1H-NMR (300 MHz, CDCI3) delta:7.61 (1 H, d, J = 16.1 Hz); 7.57.7.50 (4H, m); 7.47 (1 H, d, J = 2.21 Hz); 7.39 (1 H, dd, J = 8.46, 2.21 Hz); 6.93 (1 H, d, J = 8.46 Hz); 6.38 (1 H, d, J = 16.1 Hz); 4.27-4.17 (2H, m); 4.16-4.01 (2H, m); 2.22-2.02 (9H, m), 1 .86- 1 .70 (6H, m), 1 .54 (9H, s); 1 .52 (9H, s); 1.49 (9H, s).

The synthetic route of 85006-25-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BIOGEM S.CA.R.L.; PISANO, Claudio; DALLAVALLE, Sabrina; CINCINELLI, Raffaella; MERLINI, Lucio; (56 pag.)WO2018/60354; (2018); A1;,
Amide – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 1943-79-9, name is Phenyl methylcarbamate, 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 1943-79-9, Recommanded Product: 1943-79-9

Production Example 19-7 5-((2-Aminopyridin-4-yl)oxy)-6-(difluoromethoxy)-N-methyl-1H-indole-1-carboxamide 4-((6-(Difluoromethoxy)-1H-indol-5-yl)oxy)pyridin-2-amine described in Production Example 19-6 (4.4 mg, 0.015 mmol) was dissolved in N,N-dimethylformamide (500 muL), then 50-72% oily sodium hydride (4.1 mg) was added under nitrogen atmosphere at 0 C., and the mixture was stirred at room temperature for 30 minutes. The mixture was cooled to 0 C. again and phenyl methylcarbamate described in Production Example 1-7 (16.4 mg, 0.108 mmol) was added, and the mixture was stirred at room temperature for 50 minutes. Water and ethyl acetate were added to the reaction mixture for partition. The organic layer was washed with a saturated saline solution, then dried over anhydrous sodium sulfate and filtered, and then the filtrate was concentrated under vacuum. The residue was dissolved in dichloromethane and the resultant was purified with NH silica gel column chromatography (n-heptane:ethyl acetate=1:1-0:1-ethyl acetate_methanol=99:1-9:1), and then the target fraction was concentrated under vacuum to obtain the title compound (4.3 mg, 82%). 1H-NMR Spectrum (CDCl3) delta (ppm): 3.08 (3H, d, J=4.8 Hz), 4.44 (2H, brs), 5.49 (1H, brs), 5.91 (1H, d, J=1.8 Hz), 6.26 (1H, dd, J=6.2, 2.2 Hz), 6.50 (1H, t, J=74.0 Hz), 6.61 (1H, d, J=3.7 Hz), 7.35 (1H, s), 7.41 (1H, d, J=3.7 Hz), 7.92 (1H, d, J=5.9 Hz), 8.23 (1H, s).

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; Eisai R&D Management Co., Ltd.; Funasaka, Setsuo; Okada, Toshimi; Tanaka, Keigo; Nagao, Satoshi; Ohashi, Isao; Yamane, Yoshinobu; Nakatani, Yusuke; Karoji, Yuki; US2014/235614; (2014); A1;,
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Adding a certain compound to certain chemical reactions, such as: 6325-93-5, name is 4-Nitrobenzenesulfonamide, 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 6325-93-5, HPLC of Formula: C6H6N2O4S

General procedure: A mixture of nitroarene (1 mmol), PdCu/graphene (6 mg) and sodium borohydride (2 mmol) were taken in a 25 mL reaction tube. 3 mL of EtOH:H2O (1:2 in volume ratio) was added by a syringe at 0 C. After 10 min the reaction mixture was placed in an oil bath at 50 C. The reaction was monitored by TLC. On completion, the reaction mixture was extracted with ethylacetate and dried ove ranhydrous Mg2SO4. Evaporation of the combined organic layer andfollowed by column chromatography over silica gel (60-120 mesh) afforded desired corresponding amines.

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:
Article; Feng, Yi-Si; Ma, Jing-Jing; Kang, Yu-Mei; Xu, Hua-Jian; Tetrahedron; 36; (2014); p. 6100 – 6105;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 180079-94-1, name is tert-Butyl 3-aminophenethylcarbamate, 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 180079-94-1, Formula: C13H20N2O2

Production Example 30 Production of 3′,4′-dihydro-2’H-spiro[cyclobutane-1,1′-isoquinolin]-6′-amine 2 mL of 85 % phosphoric acid was added to 350 mg of the compound obtained in Production Example 29-2), and stirred at 70C for 1 hour. Further, 0.144 mL of cyclobutanone was added to it, and reacted at 140C for 3 hours, using a microwave reactor. The reaction liquid was diluted with water, then potassium carbonate was added to it, and extracted with ethyl acetate. This was washed with saturated saline water, dried with anhydrous magnesium sulfate, and the solvent was evaporated away. The crude product was purified through basic silica gel column chromatography (hexane/ethyl acetate) to obtain 157 mg of the entitled compound as a colorless oily compound. 1H-NMR (CDCl3) delta: 7.28 (1H, d, J=8.3 Hz), 6.59 (1H, dd, J=8.3, 2.9 Hz), 6.37 (1H, d, J=2.4 Hz), 3.54 (2H, s), 3.03 (2H, t, J=5.9 Hz), 2.68 (2H, t, J=6.1 Hz), 2.47-2.40 (2H, m), 2.18-2.07 (3H, m), 2.02-1.92 (1H, m)

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, tert-Butyl 3-aminophenethylcarbamate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Banyu Pharmaceutical Co., Ltd.; EP2168966; (2010); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 4943-86-6, 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. 4943-86-6, name is 2-Amino-N-(4-chlorophenyl)benzamide, This compound has unique chemical properties. The synthetic route is as follows.

The reaction flask was added 1l (2mmol, 493mg),and then added tert-butyl nitrite (6mmol, 0.72mL),followed by tetrabutylammonium iodide (5mol%,37 mg of) and acetonitrile (20mL). Then the system was heated for 12 hours at 60 deg C. for air, vacuum spin dry acetateAfter the nitrile with petroleum ether / ethyl acetate = 6/1 mixed solvent of a simple column chromatography to give the product 2L, 86% yield. yellowsolid,

The chemical industry reduces the impact on the environment during synthesis 2-Amino-N-(4-chlorophenyl)benzamide. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Zhengzhou Institute of Light Industry; Yan, Yi zhe; Shi, Miao miao; Liu, Yan qi; Zhi, Huan huan; He, Yuan; Niu, Bin; (18 pag.)CN105418525; (2016); A;,
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Electric Literature of 142-78-9, 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. 142-78-9, name is N-(2-Hydroxyethyl)dodecanamide, This compound has unique chemical properties. The synthetic route is as follows.

33 mg (4.5 mol %) of KBr (co-catalyst) was dissolved in 6 mL of water. Tetrahydrofuran solvent THF (31 mL), AA-TEMPO catalyst (25 mg, 2.5 mol %) and 1.5 g N-lauroylethanolamide (LMEA) were added with stirring to give a homogeneous water-white solution. Sodium hypochloride oxidizing agent (22 mL of 11.5% aq. Solution, 6.5 equivalents) and 2.3 mL of 2 NaOH (to maintain pH above 7) were mixed. The combined solution was added dropwise to the solution of LMEA and catalyst over a period of 1.5 hour. A separate aqueous layer immediately formed upon addition of the sodium hypochlorite solution. The pH of the aqueous layer was 12.7 after addition of the first 3.5 ml. The temperature was maintained below 32 C. with an ice-water bath. The reaction was stirred for 0.5 hr. more until complete conversion of LMEA to LG as determined by reversed-phase High Pressure Liquid Chromatography, abbreviated HPLC. The pH at end of the reaction was 7.6.At completion of the reaction, the mixture was acidified to pH 3.0 (to get the purified carboxylic acid) by addition of 8.5 mL of 1 N HCl, and the layers were separated. The lower aqueous layer was extracted with 30 mL THF, and the combined THF layers were concentrated on a rotary evaporator and dried in vacuo to give N-lauroylglycine in 116% yield (residual water present); Example 2 Oxidation of LMEA with 3.25 eq. of NaOCl, and Acid Work-UpThe procedure in Example 1 was followed, except that the amount of sodium hypochlorite was decreased to 3.25 equivalents. The isolated yield was 103% (includes residual water), showing that the oxidation works with the lower sodium hypochlorite amount; Example 4Oxidation of LMEA in THF with 6.5 eq. of NaOCl, Drowning Procedure at pH=2.6The procedure of Example 1 was followed except for the isolation step. After completion of the reaction, the mixture was acidified to pH=2.6 with 9.25 mL of 1 N HCl. The entire reaction mixture (both THF and water phases) were poured in 240 mL of water with vigorous stirring. The precipitated product was isolated by gravity filtration, and washed with 200 mL water. After air-drying, and further drying in vacuo, the product was obtained in 77% yield. The yield can be improved by better filtration techniques, e.g. by pressure filtration through a 0.45 mum or less filter; Example 5Oxidation of LMEA in THF with 3.25 eq. of NaOCl, Drowning Procedure, Effect of pH on YieldThe procedure of Example 2 was followed except for the isolation step. After completion of the reaction, the mixture was only partially acidified (to pH=5.2 with 3.6 mL of 1 N HCl.) The entire reaction mixture (both THF and water phases) were poured in 240 mL of water with vigorous stirring. The precipitated product was isolated by gravity filtration, and washed with 240 mL water. After drying in vacuo overnight, the product was obtained in 59% yield (based on free carboxylic acid), and 55% (based on the sodium carboxylate). The lower yield than Example 4 is attributed to the larger proportion of the water-soluble sodium carboxylate at the higher pH.

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

Reference:
Patent; Conopco, Inc.; US7307187; (2007); B1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 75175-77-8,Some common heterocyclic compound, 75175-77-8, name is 3-(4-Fluorophenyl)-N,N-dimethylacrylamide, molecular formula is C11H12FNO, 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: General procedure: A mixture of appropriately substituted arylmethyl ketone (4 mmol) and DMF-DMA (20 mmol)was refluxed for8-12 h and monitored by TLC. After complete consumption ofsubstituted methyl ketone, the mixture was subjected to rotaryevaporation under reduced pressure to remove the excess of DMFDMAand the liberated methanol. After that DMSO (6-8 mL) and 4-azidobenzenesulfonamide (4 mmol) were added to reactionmixture. After addition, reaction mixture was allowed to stir at 90C for 8-10 h in silicon oil bath. After completion, reaction mixturewas poured into water to afford required product (7a-7j). Crudeproduct thus obtained was recrystalized with ethanol.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-(4-Fluorophenyl)-N,N-dimethylacrylamide, its application will become more common.

Reference:
Article; Kumar, Rajiv; Vats, Lalit; Bua, Silvia; Supuran, Claudiu T.; Sharma, Pawan K.; European Journal of Medicinal Chemistry; vol. 155; (2018); p. 545 – 551;,
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Amide – an overview | ScienceDirect Topics