Tag: M.W=200-300

239074-29-4, name is tert-Butyl (trans-4-(hydroxymethyl)cyclohexyl)carbamate, 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. category: amides-buliding-blocks

To a solution of tert-butyl N-[4-(hydroxymethyl)cyclohexyl]carbamate (S9, 0.92 g, 4.00mmol) and N,N-diisopropylethylamine (1.05 mL, 6.00 mmol) in CH2Cl2 (20 mL, 0.2 M) cooledto 0 C was added methanesulfonyl chloride (0.34 mL, 4.40 mmol) dropwise. After 5 min thereaction was warmed to 23 C and stirred for 2 h. A saturated solution of aqueous NaHCO (30mL) was added to quench the reaction. The organic phase was separated and the aqueous phasewas extracted with CH2Cl2 (2 ¡Á 10 mL). The combined organics were dried over MgSO4,filtered, and the filtrate was concentrated under reduced pressure. The crude material was driedunder hi-vac to afford crude [4-(tert-butoxycarbonylamino)cyclohexyl]methyl methanesulfonate(S10, 1.24 g, >99% yield) which was used without further purification.

The synthetic route of 239074-29-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Allegretti, Paul A.; Horton, Timothy M.; Abdolazimi, Yassan; Moeller, Hannah P.; Yeh, Benjamin; Caffet, Matthew; Michel, Guillermina; Smith, Mark; Annes, Justin P.; Bioorganic and Medicinal Chemistry; vol. 28; 1; (2020);,
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Related Products of 956434-30-3,Some common heterocyclic compound, 956434-30-3, name is tert-Butyl 8-chloro-2,3-dihydropyrido[3,2-f][1,4]oxazepine-4(5H)-carboxylate, molecular formula is C13H17ClN2O3, 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.

(Step 1) A solution of the compound (0.500 g) obtained in Example 29, step 1, 4-benzyloxyphenylboronic acid (0.600 g) and potassium carbonate (0.243 g) in DME (10 mL) and water (1 mL) was degassed with argon gas, tetrakis(triphenylphosphine)palladium(0) (Pd(PPh3)4) (0.203 g) was added, and the reaction container was irradiated in a microwave reaction apparatus at 150C for 10 min. The reaction mixture was poured into water, and the resultant product was extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate, and concentrated. The obtained solid was recrystallized from a mixed solution of ethyl acetate and hexane to give tert-butyl 8-[(benzyloxy)phenyl]-2,3-dihydropyrido[3,2-f][1,4]oxazepine-4(5H)-carboxylate (0.483 g, 64%) as a white powder. 1H-NMR(CDCl3): delta 1.32(9H,brs), 3.74(2H,brs), 4.24(2H,brs), 4.47(2H,brs), 5.17(2H,s), 7.09(2H,d,J=8.7Hz), 7.31-7.52(5H,m), 7.58(1H,m), 7.71(1H,m), 7.97(2H,d,J=8.7Hz) MS(ESI+):433(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 tert-Butyl 8-chloro-2,3-dihydropyrido[3,2-f][1,4]oxazepine-4(5H)-carboxylate, its application will become more common.

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP2018863; (2009); A1;,
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Related Products of 885-70-1, 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. 885-70-1, name is 5,11-Dihydropyrido[2,3-b][1,4]benzodiazepin-6-one belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 6 5,11-Dihydro-11-[6-(1-piperidinyl)hexyl]-6H-pyrido-[2,3-b][1,4]benzodiazepin-6-one To a suspension of 33.2 g (0.157 mol) of 5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one in 875 ml of anhydrous dioxan, 173 ml (approx. 0.45 mol) of a 2.6 molar solution of n-butyl-lithium in n-hexane was added dropwise at ambient temperature and the resulting mixture was then stirred for another hour at the same temperature. It was then heated to 70 C. and at a reaction temperature of not more than 75 C. 83.0 g (0.034 mol) of 1-bromo6-(1-piperidinyl)hexane were added dropwise, then to complete the reaction the mixture was stirred for a further 4 hours at 80 C. After cooling, the solvent was distilled off in a water jet vacuum, the residue was adjusted to pH 7 with dilute aqueous hydrochloric acid and the mixture was then filtered. The filtrate was made alkaline with concentrated aqueous potassium hydroxide solution and extracted exhaustively with dichloromethane. The dichloromethane extracts were dried over sodium sulphate and then evaporated down and the residue remaining was digested with 100 ml of boiling diethyl ether and filtered while hot. The residue remaining after the ether had been removed was purified by chromatography on silica gel (Macherey-Nagel, 0.2-0.5 mm) using dichloromethane/methanol/cyclohexane/ethyl acetate/conc. ammonia 59/7.5/7.5/25/1 (v/v/v/v/v) as eluant. By evaporating the desired fractions and subsequently recrystallising from acetonitrile, a colourless crystalline product with a m.p. of 131 to 132 C. was obtained in a yield of 11.29 g (19% of theory). The hydrochloride melted at 223 C. (ethanol).

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, 5,11-Dihydropyrido[2,3-b][1,4]benzodiazepin-6-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Karl Thomae GmbH; US5006522; (1991); A;,
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Application of 1314538-55-0,Some common heterocyclic compound, 1314538-55-0, name is Potassium (((tert-butoxycarbonyl)amino)methyl)trifluoroborate, molecular formula is C6H12BF3KNO2, 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.

[01262] A mixture of 5- [2-chloro-5-(trifluoromethoxy)pyridin-4-yl] -2-(trifluoromethyl)pyrimidine (390 mg, 1.13 mmol, 1.00 equiv), potassium tert-butyl N-[(trifluoroboranuidyl)methyl]carbamate (350 mg, 1.47 mmol, 1.30 equiv), sodium carbonate (359 mg, 3.38 mmol, 2.98 equiv), and Pd(PPh3)2C12 (79 mg, 0.11 mmol, 0.09 equiv) in ethanol (5 mL)/water (0.5 mL) was stirred for 12 hours at 90C under nitrogen. The solid was filtered off. The filtrate was diluted with water, extracted with ethyl acetate, washed with brine, dried over anhydrous sodium sulfate, and concentrated under vacuum. The residue was purified by a silica gel colunm eluting with ethyl acetate/petroleum ether (2/1) to afford the title compound (200mg, 40%) as a light yellow solid. LCMS [M+H] 439.

The synthetic route of 1314538-55-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; ESTRADA, Anthony; VOLGRAF, Matthew; CHEN, Huifen; KOLESNIKOV, Aleksandr; VILLEMURE, Elisia; VERMA, Vishal; WANG, Lan; SHORE, Daniel; DO, Steven; YUEN, Po-wai; HU, Baihua; WU, Guosheng; LIN, Xingyu; LU, Aijun; (537 pag.)WO2016/128529; (2016); A1;,
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These common heterocyclic compound, 83948-54-3, name is tert-Butyl (5-bromopentyl)carbamate, 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. Formula: C10H20BrNO2

A solution of 4,5-dichlorobenzene-l,2-diamine (350 mg, 1.99 mmol), tert-butyl N-(5-bromopentyl)carbamate (1.05 g, 3.94 mmol), potassium carbonate (819 mg, 5.93 mmol), and sodium iodide (297 mg, 1.99 mmol) in DMF (20 mL) stirred for 18 h at 80 C. The resulting solution was cooled to room temperature, diluted with 50 mL of water, and extracted with 3×40 mL of ethyl acetate. The combined organic phases were washed with 2×30 mL of brine, dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum. The residue was purified via column chromatography with silica gel (eluting with dichloromethane/methanol (20: 1)) to give tert-butyl 5-(2-amino-4,5-dichlorophenylamino)pentylcarbamate (339 mg, 44%) as brown oil. MS: (ESI, m/z): 362[M+H]+.

The synthetic route of tert-Butyl (5-bromopentyl)carbamate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FORMA THERAPEUTICS, INC.; H. LEE MOFFITT CANCER CENTER AND RESEARCH INSTITUTE, INC.; LEE, Jennifer; BURNETTE, Pearlie; CHELLAPPAN, Srikumar; BARCZAK, Nicholas; CONTI, Chiara; ESCOBEDO, Jaime A.; HAN, Bingsong; LANCIA, David R., Jr.; LIU, Cuixian; MARTIN, Matthew W.; NG, Pui Yee; RUDNITSKAYA, Aleksandra; THOMASON, Jennifer R.; ZHENG, Xiaozhang; (322 pag.)WO2018/75959; (2018); A1;,
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Amide – an overview | ScienceDirect Topics

1314538-55-0, name is Potassium (((tert-butoxycarbonyl)amino)methyl)trifluoroborate, 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. COA of Formula: C6H12BF3KNO2

[01299] A mixture of 4-chloro-5 -(trifluoromethyl) -2-[2-(trifluoromethyl)pyrimidin-5 -yl]pyrimidine (300 mg, 0.91 mmol, 1.00 equiv), Pd(PPh3)2C12 (128 mg, 0.18 mmol, 0.20 equiv), sodium carbonate (193 mg, 1.82 mmol, 1.99 equiv), and potassium tert-butyl N-[(trifluoro-lambda4- boranyl)methyl]carbamate (216 mg, 0.91 mmol, 0.99 equiv) in t-butanol (10 mL)/water (1 mL) was stirred for 2 hours at 80C under nitrogen. The resulting solution was diluted with brine, extracted with ethyl acetate, washed with brine, dried over anhydrous sodium sulfate, and concentrated under vacuum. The residue was purified by a silica gel colunm eluting with ethyl acetate/petroleum ether (1/8) to afford the title compound (230 mg, 60%) as white solid. LCMS [M+H] 424.

The synthetic route of 1314538-55-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; ESTRADA, Anthony; VOLGRAF, Matthew; CHEN, Huifen; KOLESNIKOV, Aleksandr; VILLEMURE, Elisia; VERMA, Vishal; WANG, Lan; SHORE, Daniel; DO, Steven; YUEN, Po-wai; HU, Baihua; WU, Guosheng; LIN, Xingyu; LU, Aijun; (537 pag.)WO2016/128529; (2016); A1;,
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Amide – an overview | ScienceDirect Topics

25625-57-4, name is 2-Bromo-N-(3-(trifluoromethyl)phenyl)acetamide, 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. COA of Formula: C9H7BrF3NO

Example 6: 2-[3-(4-Bromophenyl)-2-oxo-7-oxa-1 ,4-diazaspiro[4.4]non-3-en-1 -yl]-N-[3- (trifluoromethyl)phenyl]acetamide; 3-(4-Bromophenyl)-7-oxa-1 ,4-diazaspiro[4.4]non-3-en-2-one (D21 ) (0.6g) in DMF (4ml) was cooled to ice bath temp and treated with sodium hydride (81 mg) under argon. The mixture was stirred for 30 minutes when 2-bromo-N-[3-(trifluoromethyl)phenyl]acetamide (D16) (631 mg) in DMF (3ml) was added over 2 hours by syringe pump. The mixture was then allowed to warm to room temp overnight. The solvent was partially removed then in vacuo and then poured into water and extracted with ethyl acetate. The ethyl acetate layer was dried with brine and sodium sulphate and the solvent was removed. The mixture was purified by MDAP and then crystallised by stirring with ether to give the title compound. (414mg) 1H NMR (CDCI3) delta: 2.4-2.6 (2H, m), 3.96 (1 H, m), 4.06 (1 H, m), 4.22 (1 H, m), 4.35 (3H, m), 7.4 (2H, m), 7.65 (3H, m), 7.88 (1 H, m), 8.33 (2H, m) 8.75 (1 H, br) 19F NMR (DMSO) delta: -62.8 (s), Mass Spectrum (Electrospray LC/MS): Found 496/8 (MH+). Ret. time 3.08 min.

The synthetic route of 25625-57-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; UNIVERSITY OF NOTTINGHAM; WO2008/92877; (2008); A2;,
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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 885-70-1 as follows. Recommanded Product: 5,11-Dihydropyrido[2,3-b][1,4]benzodiazepin-6-one

(a) 5,11-Dihydro-11-(prop-2-ynyl)-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one To a suspension of 7.4 g (0.035 mol) of 5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one in 150 ml of anhydrous tetrahydrofuran, 44.8 ml (approx. 0.07 mol) of a 15% solution of n-butyl-lithium in n-hexane was added dropwise with stirring at a reaction temperature of from 0 to +10 C. After it had all been added, the mixture was stirred for 30 minutes at ambient temperature before a solution of 4.16 g (0.035 mol) of 3-bromo-prop-1-yne in 25 ml of anhydrous tetrahydrofuran was added dropwise. The resulting mixture was stirred for a further 2 hours at ambient temperature, added to 1 liter of saturated aqueous saline solution and the resulting mixture was extracted exhaustively with ethylacetate. The combined ethylacetate extracts were washed twice more with 100 ml of saturated saline solution, dried over sodium sulphate with the addition of 1 g of activated charcoal and evaporated down in vacuo. The residue was purified on silica gel by chromatography using dichloromethane/ethyl acetate 95/5 (v/v) as eluant. 8.5 g (97% of theory) of colourless crystals were obtained, m.p. 199 C. (decomposition).

According to the analysis of related databases, 885-70-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Karl Thomae GmbH; US5006522; (1991); A;,
Amide – Wikipedia,
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Synthetic Route of 1939-27-1, 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. 1939-27-1 name is N-(3-(Trifluoromethyl)phenyl)isobutyramide, 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 3, put a 100ml three-necked bottle with mechanical stirring and thermometer into the ice machine, add 23ml of concentrated sulfuric acid, stir,Addition of 10.75g of iso – butyramide benzotrifluoride until the solid dissolves, keeping the temperature at -5 C, adding 2.3ml of 95% fuming HN03, stirring 3h; Step 4, the above reaction was poured into a certain amount of ice water mixture, was sticky solid, add 80g toluene, stirring,Separation, the upper organic phase was washed three times with 3% sodium bicarbonate solution, followed by three washes, and the solvent was removed by rotary evaporation to give a yellow solid; Step 5, the above yellow solid was added to the flask, 20 ml of ethanol was added, and the mixture was heated to reflux, solid 1% of activated carbon was added, stirred for 5 minutes, and hot filtered.The filtrate was cooled to room temperature, and petroleum ether was slowly added thereto until the solution became turbid. The solution was refrigerated at 0C for 3 hours, filtered, and dried at 60C to obtain flunitamide as a pale yellow solid.

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

Reference:
Patent; Xuzhou Nuokefei Pharmaceutical Technology Co., Ltd.; Zhao Qingling; Li Weixin; (7 pag.)CN108003051; (2018); A;,
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6292-59-7, name is 4-(tert-Butyl)benzenesulfonamide, 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. Product Details of 6292-59-7

A solution of compound 13 (2.0 g, 4.36 mmol) and commercially available4-tert-butylbenzenesulfoamide (1.0 g, 4.79 mmol) in toluene (30 mL) was treated withK2CO3 (723 mg, 5.23 mmol) and tetra-n-butylammonium bromide (142 mg,0.44 mmol). The reaction mixture was warmed at 100 C for 18 h and cooled downto ambient temperature. The resulting mixture was filtered through a pad of Celite,and the filtrate was diluted with EtOAc (100 mL); washed with aqueous 1N HCl,water, and brine; dried over anhydrous MgSO4; and concentrated under reducedpressure to provide the crude product. Flash chromatography (SiO2, 3percent MeOH?CH2Cl2) to provide 14 as a green foam (1.75 g, 63percent)

The synthetic route of 6292-59-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Lee, Chung Ryul; Lee, Sang Yeul; Nam, Tae-Gyu; Synthetic Communications; vol. 44; 17; (2014); p. 2488 – 2493;,
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