Tag: M.W=200-300

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 21440-97-1 as follows. SDS of cas: 21440-97-1

Example 16 General Procedure for Examples 16 to 30; A mixture of the appropriate aryl bromide (2.0 mmol), alkylene (2.2 mmol), N,N-dicyclohexylmethylamine (470 muL, 2.2 mmol) and tri-tert-butylphosphine (24 mg, 0.12 mmol) in dioxane (5 mL) was purged with nitrogen. Tris(dibenzylideneacetone)dipalladium (0) (55 mg, 0.06 mmol) was added and the mixture again purged with nitrogen and then stirred at room temperature. The reaction was monitored by LC/MS. If necessary, more catalyst was added. The reaction was diluted with ethyl acetate and filtered through a small amount of silica gel. The silica gel was rinsed with ethyl acetate and then methanol. The filtrates were kept separate and each concentrated under reduced pressure. The residues from the filtrates were analyzed for product by use of LC/MS. The product was purified by the methods described.; Step 3: (2E)-3-(2-Oxo-1,2-dihydrospiro[3,1-benzoxazine-4,1′-cyclohexan]-6-yl)but-2-enamide6-Bromospiro[4H-3,1-benzoxazine-4,1′-cyclohexan]-2(1H)-one (592 mg, 2.0 mmol), prepared in the previous step, and (E)-but-2-enamide (187 mg, 2.2 mmol) were reacted according to the General Procedure described above. By LC/MS, the methanol filtrate contained the product. The methanol filtrate was concentrated under reduced pressure to remove the solvent. The residue was taken up in ethyl acetate. Upon standing some solid precipitated. The solid was collected by filtration and dried under reduced pressure. By nuclear magnetic resonance (NMR) analysis, the solid contained ethyl acetate. The solid was taken up in methanol-methylene chloride and concentrated under reduced pressure. It was then taken up in methylene chloride and again concentrated under reduced pressure. This process was repeated two additional times and then the solid was dried under reduced pressure to give the title compound (50 mg, 8%) as a white solid, mp 204-207 C. (dec), MS m/z 301, MS m/z 299.

According to the analysis of related databases, 21440-97-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Wyeth; US2009/197878; (2009); A1;,
Amide – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 713-41-7, name is 2-Amino-4-(trifluoromethyl)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 713-41-7, Quality Control of 2-Amino-4-(trifluoromethyl)benzamide

Production Example 3 (1) 0753] A mixture of 1.0 g of 2-amino-4-trifluromethylbenzamide, 813 mg of 2-ethylsulfanylbenzaldehyde, 764 mg of sodium bisulfite and 4 ml of DMA was stirred at 150C for 8 hours. A saturated aqueous sodium bicarbonate solution and water were added to the cooled reaction mixture, and the precipitated solid was filtered. The resulting solid was washed with water and n-hexane and then dried to obtain 1.49 g of 2-(2-ethylsulfanylphenyl)-7-trifluoromethyl-3H-quinazolin-4 -one. 2-(2-Ethylsulfanylphenyl)-7-trifluoromethyl-3H-quinaz olin-4-one [0754] 1H-NMR(CDCl3)delta: 10.46(1H, brs), 8.43(1H, d), 8.11(1H, s), 7.91(1H, dd),7.72(1H, dd), 7.54 (1H, dd),7.50(1H, td), 7.41(1H, td), 2.92(2H, q), 1.28(3H, t).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Amino-4-(trifluoromethyl)benzamide, and friends who are interested can also refer to it.

Reference:
Patent; SUMITOMO CHEMICAL COMPANY LIMITED; TAKAHASHI, Masaki; ITO, Mai; NOKURA, Yoshihiko; TANABE, Takamasa; SHIMIZU, Chie; EP2865671; (2015); A1;,
Amide – Wikipedia,
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Application of 127828-22-2, 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 127828-22-2 as follows.

General procedure: To a solution of mono-Boc protected diamine linker (0.1 mmol, 1 eq) and Dasatinib- COOH (50 mg, 0.1 mmol, 1 eq) in DMF (1 mL), COMU (43 mg, 0.1 mmol, 1 eq) and DIPEA (48 mL) were added. The reaction mixture was stirred at room temperature for 1 hour, then quenched with ice cold water. Volatiles were removed in vacuum and the crude mixture was purified by preparative HPLC (METHOD 2). Fractions containing the desired product were evaporated under reduced pressure and the reside was dissolved in DCM (1 mL) and treated with a solution of anhydrous HC1 in dioxane (4M, 1 mL). After 1 hour, volatiles were removed under reduced pressure and the reside was freeze dried in order to remove any excess of acid.

According to the analysis of related databases, 127828-22-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; UNIVERSITY OF DUNDEE; CIULLI, Alessio; TESTA, Andrea; HUGHES, Scott; BUTCHER, Steven Peter; (183 pag.)WO2019/238816; (2019); 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. 141449-85-6, name is tert-Butyl hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C11H20N2O2

A round-bottom flask was charged with triphosgene (1.68 g, 5.66 mmol) and DCM (200 mL). Hexafluoroisopropanol (1.93 mL, 18.4 mmol) was added dropwise over 1 min. DIPEA(4.9 mL, 28.0 mmol) was added dropwise over 3 min. The flask contents were stirred at rt for 2 h. tert-Butyl hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate (3.00 g, 14.2 mmol) was added in one portion, and the reaction mixture was allowed to stir for 18 h at rt. The reaction mixture was then washed with 1 N HCl and brine. The organics were dried over anhydrous NazS04 and concentrated. The resulting oil was chromatographed on a silica column with a gradient (100% hexanes to 80% hexanes/20% acetone) to provide 2-tert-butyl5-(1,1,1,3,3,3-hexafluoropropan-2-yl) tetrahydropyrrolo[3,4-c]pyrrole-2,5(1H,3H)-dicarboxylate (5.74 g, 82%). 1H NMR (400 MHz,Chloroform-d) 0 5.87-5.66 (m, 1H), 3.85-3.70 (m, 2H), 3.70-3.55 (m, 2H), 3.46-3.37 (m,2H), 3.37- 3.17 (m, 2H), 2.96 (br s, 2H), 1.52 (s, 9H). ). LCMS (ESI, m/z): 429.0 [M+Ht.

The synthetic route of 141449-85-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ABIDE THERAPEUTICS, INC.; JONES, Todd, K.; CISAR, Justin, S.; GRICE, Cheryl, A.; WANG, Dong-Hui; WEBER, Olivia, D.; WO2015/3002; (2015); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 123986-64-1, 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 123986-64-1 as follows.

General procedure: The solution of (R)-1-(6-(4-(1-(3-hydroxybenzyl)-3-methyl-1H-thieno[2,3-c]pyrazole-5-carbonyl)-2-methylpiperazinmethylpiperazin-1-yl)pyridin-3-yl)ethanone (9b) (0.059 g, 120 mumol) in THF (1.0 mL)was added to tert-butyl(2-hydroxyethyl)carbamate (29.0 mg, 180 mumol), polymer supported PPh3(3 mmol/g, 120 mg) and di-2-methoxyethyl azodicarboxylate (0.051 g, 216 mumol).The mixture was stirred at room temperature for 2 h. Then, polymer supportedPPh3 (3 mmol/g, 60 mg) and the solution of di-2-methoxyethylazodicarboxylate (0.051 g, 216 mumol) in THF (0.10 mL) were added to thereaction mixture. The mixture was stirred at room temperature for 1 h. Thesolvent was evaporated by blowing away with the air at 50 C. The residue waspoured into toluene (3.0 mL) and water (1.0 mL), and stirred for 5 min. Theorganic layer was filtered on Top-Phase Separation Filter Tube, and thefiltrate was evaporated by blowing away with the air at 60 C. The residue waspurified by preparative HPLC (Actus Triart C18, eluted with MeCN/10 mM NH4HCO3aq. 10:90?100:0). Pure fractions were combined and concentrated byblowing away with the air at 50 C. The intermediate was dissolved into EtOAc(0.50 mL) and 4M HCl-EtOAc (1.0 mL) was added to the solution at room temperature.The mixture was shaken at room temperature for 10 min. Then the mixture wasevaporated by blowing away with the air at 50 C. The solution of BODIPY FLpropionic acid 1 (0.020 g, 69 mumol)in DMA (0.50 mL) and the solution of WSC(HCl) (0.016 g, 84 mumol) and HOBt(0.011 g, 84 mumol) in DMA (0.500 mL) and iPr2NEt(84 mL, 480 umol) were added to the mixture. The mixturewas stirred at room temperature for 2 h. The reaction mixture was diluted withEtOAc (3.0 mL) and quenched with water (1.0 mL), and stirred for 2 min. Theorganic layer was separated and then the aqueous layer was extracted with EtOAc(2.0 mL). The combined organic layer was evaporated by blowing away with theair at 50 C. The residue was purified by preparative HPLC (Actus Triart C18,eluted with MeCN/10 mM NH4HCO3 aq. 5:95?100:0). Purefractions were combined and concentrated by blowing away with the air at 50 Cto give the product 10 (8 mg, 9.9 mmol, 1 %).

According to the analysis of related databases, 123986-64-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Katoh, Taisuke; Yoshikawa, Masato; Yamamoto, Takeshi; Arai, Ryosuke; Nii, Noriyuki; Tomata, Yoshihide; Suzuki, Shinkichi; Koyama, Ryoukichi; Negoro, Nobuyuki; Yogo, Takatoshi; Bioorganic and Medicinal Chemistry Letters; vol. 27; 5; (2017); p. 1145 – 1148;,
Amide – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 676371-64-5, name is Methyl 3-((tert-butoxycarbonyl)amino)bicyclo[1.1.1]pentane-1-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 676371-64-5, SDS of cas: 676371-64-5

To a stirring solution of methyl 3-((tert- butoxycarbonyl)amino)bicyclo[1 .1 1 ]pentane-1 -carboxylate (0.2 g, 0.829 mmol) in THF (3.0 ml_), under nitrogen, in an ice bath was slowly added methylmagnesium bromide (3 M in Et20, 5 ml_, 3.32 mmol). After addition, the reaction mixture was stirred in the ice bath for ~10 min and then at rt for ~30 mins. The reaction was quenched with sat. aq. ammonium chloride and extracted with ethyl acetate. The organic phase was washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure to give crude tert- butyl (3-(2-hydroxypropan-2-yl)bicyclo[1 .1 1 ]pentan-1 -yl)carbamate (187 mg, 0.775 mmol, 93 % yield) as a colorless oil. 1H NMR (400 MHz, CD3SOCD3) d ppm 7.39 (br. s., 1 H), 4.1 1 (s, 1 H), 1 .70 (s, 6 H), 1 .37 (s, 9 H), 1 .03 (s, 6 H).

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, Methyl 3-((tert-butoxycarbonyl)amino)bicyclo[1.1.1]pentane-1-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; DEATON, Dave Norman; CADILLA, Rodolfo; (152 pag.)WO2019/116256; (2019); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

These common heterocyclic compound, 7326-73-0, name is 3-(N,N-Dimethylsulfamoyl)benzoic acid, 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. Product Details of 7326-73-0

To a mixture of HATU (36.25 mg, 95.35 pmol) and 3-(dimethylsulfamoyl)benzoic acid (20.04 mg, 87.40 pmol) in DCM (2.0 mL) was added DIPEA (41 .07 mg, 317.82 pmol) in one portion at 20 C under N2. The mixture was stirred at 20 C for 10 min. Then (2S)-2-amino-N-(4-phenylthiazol-2-yl)pentanamide (50.0 mg, 128.41 pmol, TFA salt) was added and the mixture was stirred at 20 C for 2 hours. The reaction mixture was concentrated under reduced pressure to give a residue. The residue was purified by prep-HPLC (TFA condition; column: Boston pH-lex 150*25 10 pm; mobile phase: [water (0.1 %TFA)- ACN]; B%: 57%-76%, 8 min) and lyophilized to give compound 17 as a white solid. 1 H NMR (400MHz, DMSO-de) d 12.52 (s, 1 H), 9.05 (d, J = 7.6 Hz, 1 H), 8.29-8.27 (m, 2H), 7.93-7.90 (m, 3H), 7.81 -7.79 (m, 1 H), 7.64 (s, 1 H), 7.54-7.39 (m, 2H), 7.38-7.27 (m, 1 H), 4.76-4.70 (m, 1 H), 2.68-2.65 (m, 6H), 1 .86-1 .83 (m, 2H), 1 .58-1 .31 (m, 2H), 0.96-0.92 (m, 3H) ppm. LCMS (ESI) m/z: [M+H]+ = 487.1. Chiral HPLC: Amycoat-MeOH(DEA)-40-7min-3mL, 2.022 min.

The synthetic route of 3-(N,N-Dimethylsulfamoyl)benzoic acid has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FOGHORN THERAPEUTICS INC.; ANTHONY, Neville, John; MILLAN, David, Simon; VASWANI, Rishi, G.; SCHILLER, Shawn, E.R.; (239 pag.)WO2019/152437; (2019); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 224309-64-2, These common heterocyclic compound, 224309-64-2, name is tert-Butyl (4-hydroxycyclohexyl)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.

To a stirred solution of tert-butyl (4-hydroxycyclohexyl)carbamate (25.0 g, 116.1 mmol, 1eq) in dry dicloromethane (250 ml_) was added triethylamine (32.2 ml_, 232.3 mmol) at 0 C under N2 atmosphere at room temperature. Mesyl chloride (10 ml_, 127.7 mmol) was added drop wise to the above reaction mixture after 15 min. Then reaction mixture was stirred at room temperature for 16 hour. The reaction mixture was quenched with aq. sodium bicarbonate, extracted with dichloromethane. The combined extracts were washed with water, brine and dried over anhydrous sodium sulphate, filtered and solvents evaporated from the filtrate under reduced pressure to obtain crude product which was purified by column chromatography to yield 25.0 g (73.5 %) of 4-((tert- butoxycarbonyl)amino)cyclohexyl methanesulfonate (INT-2). The final product was characterized by NMR.

Statistics shows that tert-Butyl (4-hydroxycyclohexyl)carbamate is playing an increasingly important role. we look forward to future research findings about 224309-64-2.

Reference:
Patent; PRIMETIME LIFE SCIENCES, LLC; JANAK, Khimchand Padia; (274 pag.)WO2019/50850; (2019); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 94838-59-2, A common heterocyclic compound, 94838-59-2, name is tert-Butyl 4-aminophenethylcarbamate, molecular formula is C13H20N2O2, 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.

A mixture of 2-(pyrrolidin-l-yl)acetic acid(l94 mg, 1.5 mmol), HATU (627 mg, l .65mmol) and DIPEA (582 mg, 4.5 mmol) in DCM (10 mL) was stirred at room temperature for 0.5 h. Then tert- butyl 4-aminophenethylcarbamate (354 mg, 1.5 mmol) was added and the reaction was stirred at room temperature overnight. TLC showed the reaction completed. The reaction mixture was concentrated and purified by column chromatography to afford the title compound as yellow solid (220 mg, 42.3 % yield). NMR (500 MHz, DMSO-riri) d: 9.74 (s, 1H), 7.53 (d, J= 8.3 Hz, 2H), 7.12 (d, J= 8.3 Hz, 2H), 6.86 (t, J= 5.3 Hz, 1H), 3.37 (s, 2H), 3.10 (dd, J= 13.9, 6.5 Hz, 2H), 2.70 (d, J= 3.3 Hz, 4H), 2.66 – 2.60 (m, 2H), 1.78 (dd, J= 6.1, 3.0 Hz, 4H), 1.37 (s, 9H).

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; ZHEJIANG VIMGREEN PHARMACEUTICALS, LTD; SUN, Sanxing; ZHAO, Long; HU, Chongbo; CHEN, Zhengshu; YE, Jinqi; (0 pag.)WO2020/2969; (2020); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Some common heterocyclic compound, 54468-86-9, name is 2-Amino-N,N-dimethylbenzenesulfonamide, molecular formula is C8H12N2O2S, 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: C8H12N2O2S

General procedure: To a solution of 2-(isopropylsulfonyl)aniline (3.0 g,15.1 mmol) in DMF (80 mL) was added sodium hydride (1.2 g,30.1 mmol, 60% in mineral oil) at 0 C. After stirring for 30 min,2,4,5-trichloropyrimidine was added to the reaction mixture followedby warming the mixture to room temperature. After stirringfor 2 h, the reaction mixture was quenched with ice and dilutedwith excess water. The precipitate was filtered and the solid wasdried by blowing nitrogen gas to obtain 3c as an off-white solid(3.75 g, 72%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 54468-86-9, its application will become more common.

Reference:
Article; Jang, Jaebong; Son, Jung Beom; To, Ciric; Bahcall, Magda; Kim, So Young; Kang, Seock Yong; Mushajiang, Mierzhati; Lee, Younho; Jaenne, Pasi A.; Choi, Hwan Geun; Gray, Nathanael S.; European Journal of Medicinal Chemistry; vol. 136; (2017); p. 497 – 510;,
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Amide – an overview | ScienceDirect Topics