Month: February 2021

Synthetic Route of 2618-96-4, 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. 2618-96-4, name is Dibenzenesulfonimide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: Under N2, ynamide 1a (0.300 mmol, 108.7 mg) and diphenylsulfonimide (2a; 0.600 mmol, 178.4 mg, 2.00 equiv) were dissolved in CH2Cl2 (4.00 mL). The reaction mixture was allowed to stir at r.t. After the consumption of 1a (4.5 h, TLC, eluent: PE-EtOAc, 4:1), the mixture was concentrated, and the residue was purified by flash chromatography on silica gel (eluent: PE-EtOAc, 6:1 ? 4:1) to afford 3a.

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, Dibenzenesulfonimide, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Yu, Lian; Deng, Yuan; Cao, Jian; Synthesis; vol. 47; 6; (2015); p. 783 – 788;,
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. 57561-39-4, name is tert-Butyl (2-hydroxyethyl)(methyl)carbamate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. category: amides-buliding-blocks

Example 6 tert-Butyl (‘2-(7-r2-r4-cvanophenoxy>>ethyll-9-oxa-3.7-diazabicvclo[3.3.11non-3- yl } ethyDmethylcarbamateOxalyl chloride (0.544 g, 0.4 mrnol) was added at -78C to a solution of DMSO (0.7 g, 0.9 mmol) in dry dichloromethane (10 mL). The resulting mixture was EPO stirred for 15 min before tert-butyl (2-hydroxyethyl)methylcarbamate (0.5 g,0.3 mmol; prepared by reaction of 2-methylaminoethanol with di-tert-butyl dicarbonate under standard conditions, using DCM as solvent), dissolved in dry dichloromethane, was added dropwise at -78C. Stirring was continued for 3 h at the same temperature, before triethylamine was added (at -78C) and the reaction mixture was warmed to -3O0C. The reaction was quenched with citric acid solution and extracted with dichloromethane. The organic layer was washed with brine and dried over sodium sulfate. Solvent evaporation yielded (0.35 g) of crude aldehyde (tert-butyl (2-oxoethyl)methylcarbamate). The crude aldehyde was then taken in DCM (10 mL). 4-[2-(9-Oxa-3,7- diazabicyclo[3.3.1]non-3-yl)ethoxy]benzonitrile (0.221 g, 0.8 mmol; see WO 01/28992), followed by acetic acid (0.182 g, 0.3 mmol), was added. After stirring for 1 h, NaBH3CN (0.188 g, 0.3 mmol) was added. The reaction mixture was stirred at RT overnight, quenched with water and extracted with dichloromethane. The organic layer was washed with water and brine and dried over sodium sulfate. Solvent evaporation under reduced pressure, followed by purification by column chromatography over silica gel using 2.5% methanol in dichloromethane as eluent, yielded 80 mg of the title compound as a pale yellow, gummy liquid. 1H NMR (300 MHz, CDCl3): delta 7.58 (2H, dd), 7.00 (2H5 dd), 4.33 (2H, t) 4.20 (2H, bs), 3.79 (2H, b), 3.58 (2H, m), 3.35 (2H, d), 3.23 (2H, d), 3.1 (6H, m), 2.92 (3H5 s), 1.41(9H, s).

The synthetic route of 57561-39-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; WO2006/135316; (2006); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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 148017-28-1 as follows. category: amides-buliding-blocks

Step b: (2R3Ry4R,5R)-2-fr(Aminosulfonyl)(f¡ãr^-butoxycarbonyl)amino1methyl}-5-(6- cMoro-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate[0462] (2R,3R,4R,5R)-2-(6-chloro-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diyl di-acetate (425.0mg, 0.001146mol), N-Boc-sulf amide (337.4mg, 0.001720mol) and triphenylphosphine (360.8mg, 0.001376mol) were dissolved in ethyl acetate (10 mL) under nitrogen and diisopropyl azodicarboxylate (338.6 muL, 0.001720mol) was added dropwise as a solution in ethyl acetate (2mL). The solution was stirred at room temperature under nitrogen for 3h. The solution was concentrated in vacuo and the residue purified by flash chromatography (DCM/ EtOAc 10% to 50%) to give product, contaminated with triphenylphosphine oxide (502mg).[0463] LCMS: R.t. 1.49 min ES+ 549 (formic acid)

According to the analysis of related databases, 148017-28-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MILLENNIUM PHARMACEUTICALS, INC.; WO2006/84281; (2006); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 154350-29-5,Some common heterocyclic compound, 154350-29-5, name is Cyclopropanesulfonamide, molecular formula is C3H7NO2S, 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 6: preparation of [18-(tert-Butyl-dimethyl-silanyloxy)-4-cyclopropanesulfonylaminocarbonyl-2,15-dioxo-3,16-diaza-tricyclo[14.3.0.04,6]nonadec-7-en-14-yl]-carbamic acid tert-butyl ester 14-tert-Butoxycarbonylamino-18-(tert-butyl-dimethyl-silanyloxy)-2,15-dioxo-3,16-diaza-tricyclo[14.3.0.04,6]nonadec-7-ene-4-carboxylic acid (500 mg, 0.86 mmoL) was dissolved in 25 mL of THF and treated with CDI (180 mg, 1.12 mmoL). (Care was taken to avoid moisture by using oven dried glassware and maintaining a dry N2 atmosphere). After refluxing the reaction mixture for two hours, it was cooled to rt and treated sequentially with cyclopropylsulfonamide (135 mg, 1.12 mmoL) and DBU (170 mg, 1.12 mmoL). After stirring for 4 h at rt, the THF was removed by rotary evaporation. The residue was partitioned between ethyl acetate and pH 4 buffer. The organic phase was dried (MgSO4), filtered, and concentrated in vacuo to give the crude product. It was then purified by flash column, eluting with 33percent ethyl acetate in hexane to isolate a white solid (300 mg, 51percent). 1H NMR (300 MHz, CD3OD) delta ppm 1H 0.07 (s, 3H), 0.08 (s, 3H), 0.85 (s, 9H), 0.87-1.49 (m, 21H), 1.73-1.95 (m, 3H), 2.08-2.16 (m, 1H), 2.25-2.36 (m, 2H), 2.42-2.56 (m, 1H), 2.85-2.93 (m, 1H), 3.65-3.74(dd, J=10.61, 3.66 Hz, 1H), 3.89 (d, J=10.25 Hz, 1H), 4.34 (m, J=9.70, 9.70 Hz, 1H), 4.43 (t, J=7.87 Hz, 1H), 4.57 (s, 1H), 4.94-5.01 (m, 1H), 5.10 (d, J=8.78 Hz, 1H), 5.66-5.75 (m, 1H), 6.55 (s, 1H), 10.13 (s, 1H). MS m/z 683 (M++1).

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

Reference:
Patent; Bristol-Myers Squibb Company; US2009/285773; (2009); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 149990-27-2, A common heterocyclic compound, 149990-27-2, name is tert-Butyl but-3-yn-1-ylcarbamate, molecular formula is C9H15NO2, 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 Cpd.4-5? (5.40 g, 12.9 mmol, 1.0 eq) and Cpd.2 (2.18 g, 12.9 mmol, 1.0 eq) in Et3N(110 mL) was added Cul (49.2 mg, 258 umol, 0.02 eq), PdCI2(PPh3)2 (181 mg, 258 umol, 0.02 eq) atC under N2 and stirred at 25 C for 16 hrs. TLC (petroleum ether/ethyl acetate = 1/1, Rf = 0.3) showthat the reaction was complete. Then aq.NH4CI (200 mL) was added, extracted with EtOAc (200mL*3), the combined organic layers were washed with brine, dried over Na2SO4 and filtered. Thefiltrate was concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel eluted with petroleum ether: EtOAc (10:1, 1:1) to give Cpd.4-6 (3.0048% yield) as yellow oil.1H NMR: ET5008-32-Plbl 400 MHz CDCI3 [17.41-7.34 (m, 1H), 7.23-7.06 (m, 3H), 4.97-4.87(m, 1H), 3.97 (s, 2H), 3.53 (t, i = 6.8 Hz, 2H), 3.43-3.33 (m, 2H), 2.72 (t, i = 8.0 Hz, 2H), 2.64 (i = 8.0 Hz,2H), 1.69-1.59 (m, 4H), 1.55-1.43 (m, 22H).

The synthetic route of 149990-27-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; OMEICOS THERAPEUTICS GMBH; MAX DELBRUeCK-CENTRUM FUeR MOLEKULARE MEDIZIN; FISCHER, Robert; SCHUNCK, Wolf-Hagen; MUeLLER, Dominik; WESSER, Tim; KONKEL, Anne; LOSSIE, Janine; (115 pag.)WO2017/168007; (2017); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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. 108-13-4, name is Malonamide, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C3H6N2O2

EXAMPLE 3 4,6-Dihydroxy-2-trifluoromethylpyrimidine, Compound VI, starting material for Step 2 Sodium hydride (900 g, 57.5% dispersion in mineral oil; 518 g active NaH; 22.5M) was stirred with 7.5 L toluene in a 22 L round-bottomed flask. Butanol was added over 5 hr. so that the pot temperature was maintained at 40. The mixture was stirred an additional 16 hr. Malonamide (765 g; 7.5 M) was added, followed by ethyl trifluoroacetate (1065 g; 7.5 M). The ensuing reaction was exothermic; the mixture was then heated on a steam-bath for 3.5 hrs. It was then stirred at 23-25 for an additional 16 hrs. The mixture was extracted with water (1*4 L and 1*2 L). The combined aqueous extracts were treated with activated charcoal and filtered. The filtrate was maintained at 10-15 as it was acidified to pH 1-2 with 37% hydrochloric acid. The mixture was chilled to 5. The solid was isolated by filtration and dried at 50 in vacuo to give 600 g (44.4% yield) VI m.p. 255-256 (Lit. 265).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 108-13-4.

Reference:
Patent; Bristol-Myers Squibb Co.; US4963678; (1990); A;,
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. 121492-06-6, name is N-Boc-(2-Aminoethyl)-N-methylamine belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Formula: C8H18N2O2

To a well stirred solution of BoC-NMe-CH2CH2-NH2 (265 mg, 1.52 mmol) in acetone (15 mL) was added a solution of Fmoc-OSu (564 mg, 1.67 mmol in 15 mL acetone). The mixture was then stirred for 2 hours at ambient temperature. TLC analysis of the reaction mixture at this stage showed formation of Boc-NMe-CH2CH2-NH-Fmoc (Rf = 0.35; 3:7 EtOAc: hexanes, UV 254 nm, TLC developed by heating with 3% (w/v) solution of ninhydrin in EtOH).After evaporation of acetone the product was purified by flash-chromatography (40 g Isco-silica column, 40 mL/min, 254 nm, 3:7 EtOAc-hexanes, 18 mL fractions collected, fractions 15-24 had pure product) to give Boc-NMe-CH2CH2-NH-Fmoc as foam (520 mg, yield = 86%). BoC-NMe-CH2CH2-NH-FmOC (520 mg, 1.31 mmol) was treated with TFA-water (15 ml, 95:5, v/v) for 1 hour at ambient temperature, when TLC analysis showed complete Boc- deprotection. TFA-water was removed under reduced pressure and the resulting oil dissolved in DCM (30 mL). To this solution, succinic anhydride (131 mg, 1.31 mmol) was added followed by DIPEA (to pH ~10 by moist pH paper). The mixture was then stirred for 30 min. The reaction mixture was then acidified (pH = 1) with HCI (1 M) and extracted with EtOAc (100 mL x 3). The combined EtOAc layers were washed with brine (100 mL x 2) and dried over Na2SO4. The EtOAc was removed under reduced pressure to give the title compound as a colorless oil. ES-MS (MeOH-direct infusion) Calculated MH+ (C23H26N2O5H+) = 411.10, Observed MH+ 411.09.

The synthetic route of 121492-06-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; APPLERA CORPORATION; WO2007/87534; (2007); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 104060-23-3, 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 104060-23-3 as follows.

Compound hA (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 with 60 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 overanhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified on silica gel (EtOAc/PE 1/15) to yield 1.0 g (40 %) of compound 11B in the form of a pale yellow solid.

According to the analysis of related databases, 104060-23-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PIERRE FABRE MEDICAMENT; JOUHANNEAUD, Alexandra; GOETSCH, Liliane; BROUSSAS, Matthieu; BEAU-LARVOR, Charlotte; CHAMPION, Thierry; ROBERT, Alain; HAEUW, Jean-Francois; RILATT, Ian; PEREZ, Michel; (244 pag.)WO2017/72196; (2017); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 1386861-46-6, 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. 1386861-46-6, name is 2-Chloro-6-methyl-N-phenylbenzamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Under an inert atmosphere, to a mixture of Example 2b (13.7 g, 55.9 mmol) in THF (100 mL) was added n-BuLi (2.5 mol/L, 44.7 mL, 111.8 mmoL) dropwise over 30 mm at -30C, which was stirred at room temperature for 1 hour. The resulting solution was used for next step directly. To a solution of Example 2c (cas: 87694-49-3, 19.5 g, 83.9 mmol) in THF (100 mL) was added i-PrMgC1 (1 mol/L, 92.2 mL, 92.2 mmol) dropwise over 30 mm. The reaction mixture was stirred at -3 0C for 1 hour, which was then added to the above mixture dropwise at -3 0C. The resulted solution was stirred at -15C for 3 hours, and then quenched with water (120 mL), followed by addition of EtOAc (300 mL). The organic layer was washed with NH4C1 (sat.), and brine, and concentrated in vacuo to give yellowish oil, which was used for next step directly without further purification. To the solution of above yellowish oil in methanol (90 mL) was added concentrated HC1 (90 mL) at room temperature. The resulting solution was stirred at 95C for 16 hours and then cooled to room temperature. The mixture was washed with brine, and concentrated in vacuo. The residue was extracted with EtOAc, and the organic layers were basified with NaHCO3 powder to pH = 8.5, and then extracted with DCM. The combined organic phases were washed with brine, concentrated and the residue was purified by silica gel chromatography (DCM/MeOH = 10/1) to give the desired product Example 2d (8.0 g, yield 48%) as a light yellow solid.?HNMR (400 MHz, Chloroform-d) 7.47 (m, 6H), 7.26 (d, J= 6.7 Hz, 2H), 6.70 (s, 1H), 3.70 (q, J 6.5 Hz, 1H), 1.25 (d, J 6.5 Hz, 3H).

The synthetic route of 2-Chloro-6-methyl-N-phenylbenzamide has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FRONTHERA U.S. PHARMACEUTICALS LLC; JIN, Bohan; DONG, Qing; HUNG, Gene; (106 pag.)WO2019/28395; (2019); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 1032350-06-3, 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. 1032350-06-3, name is tert-Butyl (1-(4-bromophenyl)cyclobutyl)carbamate, This compound has unique chemical properties. The synthetic route is as follows.

Potassium acetate (2.41 g) and 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(1,3,2-dioxaborolane) (6.25 g) are sequentially added to a DMF (25 mL) solution of the product (3.21 g) of Reference Example 56(3), and the mixture was placed in a nitrogen atmosphere. [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane complex (360 mg) was added thereto, and the mixture was stirred at 80 C. for 10 hours. The reaction mixture was cooled to room temperature, and water was added thereto, followed by extraction with ethyl acetate. The combined organic layer was washed with saturated sodium chloride, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel chromatography (hexane:ethyl acetate) to give the desired product (3.20 g, yield: 87%) as a colorless solid. 1H-NMR (CDCl3) delta: 7.79 (2H, d, J=8.0 Hz), 7.43 (2H, d, J=8.0 Hz), 5.07 (1H, br s), 2.59-2.31 (4H, m), 2.14-2.03 (1H, m), 1.90-1.78 (1H, m), 1.36 (9H, s), 1.34 (12H, s) ESI-MS m/z 374 (MH+)

The chemical industry reduces the impact on the environment during synthesis tert-Butyl (1-(4-bromophenyl)cyclobutyl)carbamate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; TAIHO PHARMACEUTICAL CO., LTD.; Nakamura, Masayuki; Niiyama, Kenji; Kamijo, Kaori; Ohkubo, Mitsuru; Shimomura, Toshiyasu; US2014/5185; (2014); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics