Tag: M.W=200-300

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., Computed Properties of C11H14FNO2

To a solution of 4-fluorophenylcarbamic acid terf-butyl ester (1.02 g, 4.6 mmol) in tetrahydrofuran (15 mL) was added sodium hydride (60% dispersion in mineral oil, 206 mg, 5.1 mmol). After the initial gas evolution had ceased, the reaction was allowed to stir for 15 minutes. Tetra-n-butylammonium iodide (189 mg, 0.5 mmol) was then added followed by the addition of 1-(4-chloromethyl-thiazol-2-yl)-piperidine (1.1 g, 5.1 mmol) prepared above. The mixture was heated to reflux for 1 hour. After cooling, the reaction was carefully neutralized with cold saturated sodium bicarbonate (10 ml_) and extracted with ethyl acetate (2 x 20 mL). The organic layers were combined, dried over anhydrous sodium sulfate, filtered and the solvent removed under reduced pressure to provide an oil. Flash chromatography (silica gel; 10% ethyl acetate in hexanes) provided (4-fluorophenyl)-(2-piperidin-1-yl-thiazol-4- ylmethyl)-carbamic acid te/t-butyl ester (1.25 g, 3.2 mmol) as a white solid.

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; WYETH; WO2008/73461; (2008); A2;,
Amide – Wikipedia,
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Reference of 121-30-2,Some common heterocyclic compound, 121-30-2, name is 4-Amino-6-chlorobenzene-1,3-disulfonamide, molecular formula is C6H8ClN3O4S2, 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.

1 kg of 4-amino-6-chloro-1,3-benzenedisulfonamide was mixed with 10 kg of purified water, stirred and heated to 80 C, and 0.5 kg of formaldehyde was added dropwise, and the addition was completed in about two hours. And reacted at 100 C for 0.5 hour. Cooling to 15 , adding 0.3 kg of sodium hydroxide, 0.07 kg of medicinal charcoal, 60 C stirring for 30 minutes, insulation filter. The filtrate stirring to adjust the pH value of 5.5, cooling down to 20 below the centrifugal dehydration, and with a small amount of purified water leaching, drying wet boutique. After drying crushed and packaged, the product of hydrochlorothiazide.The product was white crystalline powder and was detected by high performance liquid chromatography, which was consistent with the retention time of the main peak of the hydrochlorothiazide standard. The UV spectrum was detected at 273nm and 323nm, and the absorbance at the wavelength of 273nm was the same as that at 323nm The absorbance ratio was 5.7; consistent with the infrared absorption profile of the hydrochlorothiazide standard.The residual methanol in the product does not exceed 0.3%, the ethanol does not exceed 0.5%, the weight loss is not more than 0.5%, the ignition residue does not exceed 0.1%, the pH, chloride, heavy metal and microbial limit are in accordance with the provisions of the Chinese Pharmacopoeia 2010 edition The Calculated according to dry goods, C7H8ClN3O4S2 content of 99.2%.

The synthetic route of 121-30-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Anyang Jiuzhou pharmaceutical Co., Ltd; Cao, Junhua; (4 pag.)CN103396381; (2016); B;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Some common heterocyclic compound, 141449-85-6, name is tert-Butyl hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate, molecular formula is C11H20N2O2, 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: 141449-85-6

Example 90A 5-(6-Chloro-pyridazin-3-yl)-hexahydro-pyrrolo[3,4-c]pyrrole-2-carboxylic Acid tert-butyl Ester The product of Example 6c (1.5 g, 7.1 mmol) was dissolved in 1,4-dioxane (35 mL). 3,6-Dichloropyridazine (Aldrich, 1.37 g, 9.2 mmol), tris(dibenzylideneacetone)dipalladium (0) (Pd2(dba)3, Strem, 0.28 g, 0.31 mmol), 1,3-bis(2,6-di-1-propylphenyl)imidazolium chloride (Strem, 0.38 g, 0.90 mmol), and Cs2CO3 (6.97 g, 21.2 mmol) were added and the mixture was stirred at 85 C. for 18 h, then cooled to room temperature, filtered and concentrated under vacuum. The residue was triturated with 80% EtOAc-hexanes (50 mL) and the resulting solid was filtered and dried under vacuum to give 0.81 g of the title compound (2.5 mmol, 35% yield). MS (DCl/NH3) m/z 325 (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 141449-85-6, its application will become more common.

Reference:
Patent; Basha, Anwer; Bunnelle, William H.; Dart, Michael J.; Gallagher, Megan E.; Ji, Jianguo; Li, Tao; Pace, Jennifer M.; Ryther, Keith B.; Tietje, Karin R.; Mortell, Kathleen H.; Nersesian, Diana L.; Schrimpf, Michael R.; US2005/101602; (2005); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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. 127828-22-2, name is tert-Butyl (2-(2-aminoethoxy)ethyl)carbamate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Formula: C9H20N2O3

Step 1t-Butyl (2-(2-aminoethoxy)ethyl)carbamate (204 mg, 1 mmol) was dissolved in saturated aq. NaHCO3 (1 0 mL). The solution was cooled to 0 C. Methyl-2,5-dioxo-2,5- dihydro-1 H-pyrrole-1 -carboxylate (155 mg, 1.0 mmol) was then added. The reaction was stirred for 1 .5 h at 0 C. The pH was adjusted to 1 -2 with 2M HCl, and the mixture was extracted with EtOAc (3 X 20 mL). The combined organic phases was washed with brine, dried over MgSO4, filtered, and concentrated. The residue was purified by ISCO using a 0-4% gradient of MeOH in DCM to obtain tert-butyl (2-(2-(2,5-dioxo-2,5-dihydro-1 H-pyrrol- 1 -yl)ethoxy)ethyl)carbamate. 1H NMR (400 MHz, CD3OD): 6.82 (s, 2H), 3.68 (t, J = 5.4 Hz, 2H), 3.59 (t, J = 5.4 Hz, 2H), 3.46 (t, J = 5.6 Hz, 2H), 3.1 8-3.14 (m, 2H), 1.43 (s, 9H). MS m/z 1 85.1 (M+1 -Boc). Retention time 0.918 min.

The synthetic route of 127828-22-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; GEIERSTANGER, Bernhard; GRUNEWALD, Jan; OU, Weijia; PAN, Shifeng; UNO, Tetsuo; WAN, Yongqin; WANG, Xing; WO2015/189791; (2015); A1;,
Amide – Wikipedia,
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Electric Literature of 362670-09-5,Some common heterocyclic compound, 362670-09-5, name is N1-Boc-5-methoxy-1,2-benzenediamine, molecular formula is C12H18N2O3, 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.

Example M51 {5-Methoxy-2-[3-oxo-3-(3-pyridin-3-yl-phenyl)-propionylamino]-phenyl}-carbamic acid tert-butyl ester The title compound was prepared from (2-Amino-5-methoxy-phenyl)-carbamic acid tert-butyl ester (Example J12) (179 mg, 0.75 mmol) and 3-oxo-3-(3-pyridin-3-yl-phenyl)-propionic acid tert-butyl ester (Example K1) (223 mg, 0.75 mmol) according to the general procedure M. Obtained as a light brown foam (256 mg). MS (ISN) 460.3 [(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 N1-Boc-5-methoxy-1,2-benzenediamine, its application will become more common.

Reference:
Patent; Adam, Geo; Goetschi, Erwin; Wichmann, Juergen; Woltering, Thomas Johannes; US2003/166639; (2003); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 478837-18-2, name is tert-Butyl 3-hydroxy-8-azabicyclo[3.2.1]octane-8-carboxylate, 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 478837-18-2, HPLC of Formula: C12H21NO3

tert-Butyl 3-hydroxy-8-azabicyclo[3.2.1 ]octane-8-carboxylate as obtained in step 1 (100 mg, 2.0 mmol), acetonitrile (2 mL) and 4 M hydrogen chloride in 1,4-dioxane (2 mL) were combined and stirred at 700C for 15 minutes. The reaction mixture was concentrated and dried to give 8-azabicyclo[3.2.1]octan-3-ol hydrochloride salt (71 mg, 100% yield). MS (EI) for C7H13NO: 128 (MH+).

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; EXELIXIS, INC.; AAY, Naing; BLAZEY, Charles, M.; BOWLES, Owen, Joseph; BUSSENIUS, Joerg; CURTIS, Jeffry, Kimo; DEFINA, Steven, Charles; DUBENKO, Larisa; HARRIS, Jason, R.; JACKSON-UGUETO, Eileen, E.; KIM, Angie, Inyoung; MANALO, Jean-claire, Limun; PACK, Michael; PETO, Csaba, J.; RICE, Kenneth, D.; TSANG, Tsze, H.; WANG, Longcheng; WO2010/138490; (2010); A1;,
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Amide – an overview | ScienceDirect Topics

Reference of 72505-21-6,Some common heterocyclic compound, 72505-21-6, name is 4-(Trifluoromethyl)thiobenzamide, molecular formula is C8H6F3NS, 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.

5.0 g of Methyl 3-oxoheptanoate were dissolved in 80 ml dry dichloromethane. 2.82 ml Sulfurylchloride was added and the reaction mixture was stirred at room temperature for thirty minutes. Water was added and the mixture was extracted five times with dichloromethane (30 ml). The combined organic extracts were washed with water and brine and dried over MgSO4. The solvent was evaporated in vacuo to obtain 6.0 g 2-Chloro-3-oxo-heptanoic acid methyl ester as crude material. 6.0g 2-Chloro-3-oxo-heptanoic acid methyl ester was dissolved in 50 ml ethanol and 6.4 g 4-(Trifluoromethyl)thiobenzamide was added. The mixture was heated under reflux overnight. The cooled reaction mixture was evaporated in vacuo and column chromatography (n-heptane:ethyl acetate = 100:1 => 60:1) of the residue gave 7.4 g 4-Butyl-2-(4-trifluoromethyl-phenyl)-thiazole-5-carboxylic acid methyl ester as yellow oil. C16H16F3NO2S (343.37), MS(ESI): 344.1 (M+H+), Rf(n-heptane:ethyl acetate = 4:1) = 0.62.

The synthetic route of 72505-21-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Aventis Pharma Deutschland GmbH; EP1586573; (2005); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

These common heterocyclic compound, 4093-29-2, name is Methyl 4-acetamido-2-methoxybenzoate, 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. Safety of Methyl 4-acetamido-2-methoxybenzoate

At room temperature,Compound 64A (2.2 g, 10.0 mmol)Suspended in three volts of acetic anhydride, stirred until fully cooled to -10 C,Concentrated nitric acid (4 mL, 50 mmol) was slowly added dropwise at this temperature.After the dropwise addition, the temperature was raised to room temperature, and stirring was continued for 3 hours, and then the reaction liquid was poured into ice water.Extract with ethyl acetate (100 mL ¡Á 3), combine the organic phases, and dry.Concentration under reduced pressure gave compound 64B (2.8 g, 67%).

The synthetic route of Methyl 4-acetamido-2-methoxybenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Jiangsu Xiansheng Pharmaceutical Co., Ltd.; Chen Huanming; Liang Bo; Cao Wenjie; Zhang Guiping; Zhao Zhongqiang; Jiang Zhaojian; Zuo Gaolei; Xu Wanmei; Gong Hongju; Zhang Peng; Wang Jianghuai; Li Qingsong; Gao Chunhua; (79 pag.)CN104045552; (2019); B;,
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. 88612-71-9, name is Ethyl 4-oxo-4H-quinolizine-3-carboxylate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Quality Control of Ethyl 4-oxo-4H-quinolizine-3-carboxylate

EXAMPLE 1 To a solution of 3-ethoxycarbonyl-4H-quinolizin-4-one (2.17 g) in methanol (65.2 ml) was added dropwise 6 N aqueous sodium hydroxide (6.5 ml) at room temperature. After stirring for 20 minutes, water (10 ml) was added. After stirring for 20 minutes, water (30 ml) was also added. After stirring for an hour, the reaction mixture was acidified to pH 3 with 4N aqueous hydrochloric acid. The precipitate was filtered and washed with water to give 4H-quinolizin-4-one-3-carboxylic acid (1.75 g) as pale yellow crystal. mp 233 C. IR (Nujol): 1730, 1610, 1585, 1320 cm-1 NMR (DMSO-d6) delta: 7.26 (d, 1H, J=9 Hz), 7.50-7.95 (m, 1H), 8.00-8.20 (m, 2H), 8.41 (d, 1H, J=9 Hz), 9.20-9.40 (m, 1H)

The synthetic route of 88612-71-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Fujisawa Pharmaceutical Co., Ltd.; US4698349; (1987); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 51-06-9, name is 4-Amino-N-(2-diethylaminoethyl)benzamide, 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 51-06-9, Computed Properties of C13H21N3O

Example V 4-[(Butylsulfonyl)amino]-N-[2-(diethylamino)ethyl]benzamide hydrobromide To 100 ml of methylene chloride add 6.52 g (36.2 mmole) of 4-amino-N-[2-(diethylamino)ethyl]benzamide and cool to -78 C. under nitrogen atmosphere. To this solution slowly add 5.61 g (36.2 mmole) of n-butanesulfonyl chloride. When the addition is complete, allow the reaction mixture to warm to room temperature and monitor by thin layer chromatography on silica gel (acetonitrile:ammonium hydroxide, 9:1). Upon completion of the reaction remove the solvent in vacuo. To the resulting oil add 50 ml H2 O followed by 50% sodium hydroxide until pH=14. Extract the aqueous layer with 3*50 ml diethyl ether and 2*25 ml of methylene chloride. To the aqueous layer add concentrated HCl to bring the pH to 8.5. Extract the aqueous solution with 3*75 ml of methylene chloride. Combine the extracts and dry over sodium sulfate. Filter the drying agent and remove the solvent in vacuo. Dissolve the resulting oil in acetonitrile. Bubble HBr gas through the solution until pH=1. Remove the solvent in vacuo. Triterate the resulting oil in diethyl ether and ethyl acetate to yield a precipitate. Isolate by filtration and recrystallize from MeOH/ethyl acetate to afford the title compound. NMR (DMSO-d6): delta=0.82(t,3), 1.22(t,6), 1.34(m,2), 1.63 (m,2), 3.23(m,8), 3.57(m,2), 7.26 (d,2), 8.67(t,1), 9.22(br s,1) and 10.19(s,1)ppm.

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:
Patent; Schering A.G.; US4544654; (1985); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics