Tag: M.W=100-200

Reference of 6274-22-2,Some common heterocyclic compound, 6274-22-2, name is 4-Amino-N-methylbenzamide, molecular formula is C8H10N2O, 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 5 Method H: 4-(4-(5,6,7,8-tetrahydro-7,7-dimethyl-4-oxo-4H-thiazolo[5,4-c]azepin-2-yl)pyridin-2-ylamino)-N-methylbenzamide (I-5) 2-(2-chloropyridin-4-yl)-5,6,7,8-tetrahydro-7,7-dimethylthiazolo[5,4-c]azepin-4-one (70 mg, 1.0 Eq.), 4-amino-N-methyl-benzamide (41 mg, 1.2 Eq.), NaOtBu (61 mg, 2.8 Eq.), Pd(OAc)2 (5 mg, 0.1 Eq.) were suspended/dissolved in dry toluene and degassed (vacuum/N2 cycles*5). 2-Di-tert-butylphosphino)biphenyl (143 mg, 0.2 Eq.) was then added. The resultant mixture was then refluxed overnight. A further portion of NaOtBu (61 mg, 2.8 Eq.), Pd(OAc)2 (5 mg, 0.1 Eq.) and 2-(di-tert-butylphosphino)biphenyl (14 mg, 0.2 Eq.) were added, followed by dry dioxane (0.5 mL). The resultant mixture was refluxed for a further night. The reaction mixture was allowed to cool to RT, partitioned between EtOAc/MeOH (3:1)/NH4Cl, and then extracted into EtOAc/MeOH (3:1) (3*50 mL). The combined organic layers were washed with brine (1*20 mL), dried over Na2SO4, filtered and concentrated under reduced pressure. Purification was achieved using column chromatography (10% MeOH/90% DCM) to obtain the title compound as a bright yellow powder (18.6 mg, 19% yield); 1H NMR (DMSO D6) 1.0 (6H, s), 2.8 (3H, d), 3.0 (2H, s), 3.0 (2H, m), 7.3 (1H, m), 7.5 (1H, s), 7.8 (4H, s), 8.2 (1H, m), 8.3 (2H, m), 9.6 (1H, s); LC/MS M+1 (obs.) 422.20; LC/MS M-1 (obs.) 420.30.

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-methylbenzamide, its application will become more common.

Reference:
Patent; Vertex Pharmaceuticals Incorporated; US2009/281082; (2009); A1;,
Amide – Wikipedia,
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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. 148890-63-5, name is 5-Amino-2H-benzo[b][1,4]oxazin-3(4H)-one, A new synthetic method of this compound is introduced below., category: amides-buliding-blocks

Synthesis of 3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-5-sulfonyl chloride Into a 500 ml 3-necked round-bottom flask, was placed a solution of 5-amino-2H-benzo[b][1,4]oxazin-3(4H)-one (5 g, 28.96 mmol, 1.00 equiv 95%) in CH3CN (300 mL). To the above was added HOAc (24.9 g) dropwise with stirring, while cooling to a temperature of 0 C. To the above was added HCl (16.2 g, 36.5%) dropwise with stirring, while cooling to a temperature of 0 C. This was followed by the addition of a solution of NaNO2 (2.52 g, 36.52 mmol, 1.20 equiv) in H2O (2 mL), which was added dropwise with stirring, while cooling to a temperature of 0 C. The resulting solution was allowed to react with stirring, for 30 min while the temperature was maintained at 0 to 5 C. in a bath of H2O/ice. This was followed by and maintained with an atmosphere of sulfur dioxide, the resulting solution was allowed to react, with stirring, for an additional 2 h while the temperature was maintained at 0–5 C. in a bath of H2O/ice. To the mixture was added CuCl2.2H2O (5.11 g, 29.97 mmol, while cooling to a temperature of 0 to 5 C. The resulting solution was allowed to react, with stirring, maintained with an atmosphere of sulfur dioxide for an additional 2 h while the temperature was maintained at 0–5 C. in a bath of H2O/ice. The resulting solution was allowed to react, with stirring, overnight while the temperature was maintained at 25 C. The reaction progress was monitored by TLC (PE:EtOAc=1:1). The reaction mixture was then quenched by the adding 200 mL of H2O/ice. The resulting solution was extracted 3 times with 300 mL of dichloromethane and the organic layers combined. The resulting mixture was washed 5 times with 200 mL of brine. The mixture was dried over MgSO4. The residue was purified by eluding through a column with a 1:15 EtOAc/PE solvent system. This resulted in 0.9 g (11%) of 3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-5-sulfonyl chloride as a light yellow solid. LC-MS (ES, m/z): [M+C5H11N2-Cl]+ calcd for C13H17N3O4S 312, found 312 1H NMR (CDCl3, 300 MHz, delta): 9.06(1H,s), 7.69(1H,d), 7.36(1H,m), 7.18(1H,d), 4.75(2H),s)

The synthetic route of 148890-63-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MEMORY PHARMACEUTICALS CORPORATION; US2008/200471; (2008); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 147751-16-4, 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 147751-16-4 as follows.

LiAlH4 (9.0 mL of a 1 M solution in THF, 9.0 mmol) was added dropwise to a suspension of 2-ethylpyridine-3-carboxylic acid (500 mg, 3.31 mmol) in THF (5 mL) under N2 with cooling in an ice bath. The resulting solution was stirred for 1 hour, then quenched by the careful addition of water (0.35 mL) then aqueous NaOH (0.25 mL of a 15% w/v solution) then water (1 mL). After stirring for 10 minutes the mixture was filtered and the filtrate concentrated in vacuo to give a colourless oil (250 mg); MS m/z: 138 (M+H)+. This material was dissolved in DCM (10 mL) and tert-butyl N-methylsulfonylcarbamate (630 mg, 3.23 mmol) and PPh3 (950 mg, 3.62 mmol) were added followed by DEAD (500 muL, 3.04 mmol). The reaction mixture was stirred at ambient temperature for 18 hours, then partitioned between EtOAc and saturated aqueous sodium bicarbonate solution. After stirring for 5 minutes the organic phase was isolated using a phase separation cartridge. The solvent was removed in vacuo and the residue purified by column chromatography (silica, DCM-EtOAc elution) to give an oil that was taken up in HCl (10 mL of a 3 M solution in MeOH). PtO2 (150 mg, 0.66 mmol) was added and the mixture shaken in a Parr hydrogenator for 18 hours under 60 psi of H2 pressure. The reaction mixture was poured onto a pre-wetted ion-exchange cartridge, washing with MeOH then eluting the product with 2 M methanolic NH3 solution. The filtrate was concentrated in vacuo to give N-((2-ethylpiperidin-3- yl)methyl)methanesulfonamide A74 as a colourless oil (70 mg) that was taken directly on to the next reaction without further purification; MS m/z: 221 (M+H)+.

According to the analysis of related databases, 147751-16-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK PATENT GMBH; VERTEX PHARMACEUTICALS INCORPORATED; BAYLY, Andrew; BLEICH, Matthew; CHARRIER, Jean-Damien; DODD, James; DURRANT, Steven; ENO, Meredith Suzanne; ETXEBARRIA I JARDI, Gorka; EVERITT, Simon; FRAYSSE, Damien; KELLY, Shazia; KNEGTEL, Ronald; MOCHALKIN, Igor; MORTIMORE, Michael; NORTH, Kiri; PORICHIS, Filippos; PULLIN, Robert; RUTHERFORD, Alistair; STORCK, Pierre-Henri; TWIN, Heather Clare; XIAO, Yufang; (1159 pag.)WO2019/148132; (2019); A1;,
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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 14719-21-2 as follows. category: amides-buliding-blocks

Vl.j .dN-[3-(6-Benzyloxy-pyridazin-3-yl)-prop-2-vnyl1-2,2,2-trifluoro-acetamide; 16.7 g (50.0 mmol) Trifluoro-methanesulfonic acid 6-benzyloxy-pyridazin-3-yl ester and 15.1 g (100.0 mmol) 2,2,2-trifluoro-N-prop-2-ynyl-acetamide are dissolved in 150 ml THF and 75 ml triethyl amine. 1.4 g (2.0 mmol) bis-(triphenylphosphine)palladiumdichloride and 1.40 g (7.35 mmol) copper-(l)-iodide are added at -5C. The mixture is stirred for 20 hours at RT. After that time the solvent is evaporated. The residue is taken up in ethyl acetate and washed with water. The organic phase is dried over sodium sulphate, the solvent is evaporated. The product is washed with tert-butyl methyl ether and dried at 80C. Yield: 9.50 g (57% of theory),Rf value: 0.50 (silica gel, methylene chloride/ethyl acetate = 5:1 ) M. p. 163-166C C-IeH-I2FsNsO2

According to the analysis of related databases, 14719-21-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BOEHRINGER INGELHEIM PHARMA GMBH & CO. KG; WO2007/48802; (2007); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 2227-79-4, These common heterocyclic compound, 2227-79-4, name is Benzothioamide, 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.

General procedure: To a stirred solution of aryl thioamide or amidine (1 mmol) in 5 mL distilled water was added alpha-tosyloxyketone (1 mmol) and the reaction mixture stirred at 60 C or 80 C till completion. Progress of the reaction was monitored by thin layer chromatography. After completion of the reaction, product was readily filtered and recrystallized from ethanol (3a-k, 3p-o and 4a-e). In some cases (3l-m and 4f-i) product was extracted with dichloromethane (25 mL), washed with brine (25 mL), the organic layers were combined, dried over anhydrous Na2SO4 and distilled off in vacuum. The residue so obtained was purified by column chromatography on silica gel (100-200 mesh) (EtOAc/Hexane) to give pure product.

Statistics shows that Benzothioamide is playing an increasingly important role. we look forward to future research findings about 2227-79-4.

Reference:
Article; Kumar, Dalip; Kumar, N. Maruthi; Patel, Gautam; Gupta, Sudeep; Varma, Rajender S.; Tetrahedron Letters; vol. 52; 16; (2011); p. 1983 – 1986;,
Amide – Wikipedia,
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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. 5900-59-4, name is 2-Amino-4-chlorobenzamide, A new synthetic method of this compound is introduced below., name: 2-Amino-4-chlorobenzamide

Reference example 2: 7-chloro-4(3H)-quinazolone 2-Amino-4-chlorobenzamide (25.6 g, 0.150 mol) obtained in Reference example 1 was dissolved in trimethyl orthoformate (560 ml), and to this added was concentrated hydrochloric acid (15 ml), and the mixture was stirred at room temperature for 1 hour. After completion of the reaction, the reaction solution was filtered, and the crude crystal filtered was suspended in water (250 ml) and neutralized with 3N NaOH aqueous solution. The neutralized solution was filtered, the solid being washed with water on the funnel to give 20.9 g (yield 77percent) of the title compound as white crystal.

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; Japan Energy Corporation; EP1229025; (2002); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 154350-29-5, 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 154350-29-5 as follows.

To a solution of Boc-D-beta-vinyl cyclopropane amino acid (4.5g) in DMF was added CDI (3.97g). The reaction mixture was stirred at 4O0C for Ih and then added cyclopropylsulfonamide (4.66g) and DBU (5.78ml). The reaction mixture was stirred overnight at 4O0C. The reaction mixture was extracted with EtOAc. The organic extracts were washed with IM NaHCO3, brine, dried over Na2SO4, filtered and concentrated. The residue was desolved in 4NHCL/Dioxane. The reaction was stirred at RT for lhour and then concentrated in vacuo. The resulted solid was carrired out to next step without further purification. MS (ESI): m/z = 231.10 [M+H].

According to the analysis of related databases, 154350-29-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ENANTA PHARMACEUTICALS, INC.; WO2009/79352; (2009); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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. 7150-72-3, name is tert-Butyl vinylcarbamate, A new synthetic method of this compound is introduced below., Application In Synthesis of tert-Butyl vinylcarbamate

In a Schlenck tube, tert-butyl N-ethenylcarbamate 7a (1.74 eq., 100 mg, 0.698 mmol) andtBuOK (1.91 eq., 86 mg, 0.766 mmol) were dissolved in DMSO (1 mL) under air atmosphereat 55 C. The mixture was stirred for 1 minute. Then 1,10-phenanthroline (2.6 eq., 188 mg, 1.05mmol) and ((thiophene-2-carbonyl)oxy)copper (1.29 eq., 99 mg, 0.519 mmol) were added. Theresulting mixture was stirred for another minute. Finally (2-bromoethynyl)benzene 8a (1 eq.,72.8 mg, 0.05 mL, 0.402 mmol) as a DMSO solution (1 mL) was added to the mixture. After10 minutes, the reaction was complete as judged by TLC (99:1, petroleum ether:ethyl acetate).The mixture was diluted with EtOAc, filtered over a pad of silica gel, washed with water andthen the organic layer was dried over MgSO4. After filtration, the solvent was removed undervacuum. The crude oil was purified by silica gel chromatography (100:0 to 95:5, petroleum ether:ethyl acetate) to give tert-butyl N-ethenyl-N-(2-phenylethynyl)carbamate 5a (69.5 mg,0.286 mmol, 74%) as slightly yellow oil.

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:
Article; Le Fouler, Vincent; Duret, Guillaume; Bisseret, Philippe; Blanchard, Nicolas; Tetrahedron Letters; vol. 59; 36; (2018); p. 3349 – 3352;,
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. 513-74-6, name is Ammonium carbamodithioate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. category: amides-buliding-blocks

Methyl Dithiocarbamate (I) [2] In a 500mL three-necked flask, provided with a gas-inlet tube, a stirrer, and a gas outlet combined with a thermometer, are placed dry THF(140mL) and carbon disulfide (16.7g, 0.22mol). Ammonia is then introduced with continuous stirring, the flow of ammonia being adjusted in such a way that a slow stream is leaving the flask. The temperature is allowed to rise to 40-45 °C and is kept at that level by occasional cooling. When, after 1h, no more heat is evolved and the temperature has dropped to 35 °C, the flask is evacuated (rotary evaporator) to remove some dissolved ammonia. Water (25mL) is then added to dissolved the white precipitate. To the resultant mixture of THF and aqueous ammonium dithiocarbamate, dimethylsulfate (25.2g, 0.2mol) is added with vigorous stirring. During the addition (which requires 30min), the temperature of the mixture is allowed to rise to 45-50 °C and is maintained at that level for 15 min by occasional cooling. Then, concentrated aqucous ammonia (5mL) is added to destroy excess dimethyl sulfate and stirring is continued for 15min. The upper layer is separated and dried with magnesium sulfate (without being washed). The aqueous layer is extracted with EA (3*20mL) and the organic phases are combined. The solution is concentrated in a water-pump vacuum and the last traces of solvent are removed at 0.5-1 torr by means of an oil pump to leave nearly pure methyl dithiocarbamate(I); yield: 20g (93percent, calculated on dimethyl sulfate).

The synthetic route of 513-74-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shin Nippon Biomedical Laboratories, Ltd.; SUZUKI, Nobuyuki; YAMASHITA, Hidetoshi; (156 pag.)EP3018125; (2016); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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. 1118-69-0, name is N-Isopropylacetamide, A new synthetic method of this compound is introduced below., SDS of cas: 1118-69-0

A 100 mL Schlenk flask fitted with a reflux condenser was charged with tetrakis(dimethylamido)zirconium (0.200 g, 0.748 mmol) and toluene (10 mL). A solution of N-isopropylacetamide (0.302 g, 2.99 mmol) in toluene (10 mL) was added slowly and the resultant mixture was refluxed for 3 h. Upon cooling to room temperature, the volatile components were removed under reduced pressure and sublimation of the crude solid at 110 C/0.05 Torr afforded 3 as colorless crystals (0.188 g, 51%): mp 206-209 C; IR (Nujol, cm-1) 1576 (s), 1456 (s), 1403 (s), 1363 (s), 1342 (s), 1319 (m), 1186 (s), 1170 (m), 1126 (m), 1051 (m), 987 (m), 886 (m), 822 (m), 814 (m), 614 (s), 582 (s); 1H NMR (C6D6, 23 C, delta) 3.34 (septet, J = 6.2 Hz, 4H, CH(CH3)2), 1.71 (s, 12H, CH3), 1.24 (d, J = 6.2 Hz, 24H, CH(CH3)2); 13C{1H} NMR (C6D6, 23 C, ppm) 183.00 (s, C=O), 48.94 (s, CH(CH3)2), 23.86 (s, CH(CH3)2), 17.06 (s, CH3). Anal. Calcd for C20H40N4O4Zr: C, 48.85; H, 8.20; N, 11.39. Found: C, 48.69; H, 8.06; N, 11.44.

The synthetic route of 1118-69-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Karunarathne, Mahesh C.; Baumann, Joseph W.; Heeg, Mary Jane; Martin, Philip D.; Winter, Charles H.; Journal of Organometallic Chemistry; vol. 847; (2017); p. 204 – 212;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics