Author: Jessica.F

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;,
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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;,
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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. 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;,
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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;,
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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;,
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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;,
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Some common heterocyclic compound, 198211-38-0, name is tert-Butyl 3-azabicyclo[3.1.0]hexan-6-ylcarbamate, molecular formula is C10H18N2O2, 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 tert-Butyl 3-azabicyclo[3.1.0]hexan-6-ylcarbamate

General procedure: Intermediate C17.ii (130 mg) and K2C03 (69 mg) were suspended with DMF. 6-(Boc-amino)-3-azabicyclo[3. 1.0]hexane (81 mg; commercial) was added portionwise and themixture was stirred at rt for 1 day. The mixture was concentrated under reduced pressure and the residue was portioned between EA and water. The aq. layer was extracted with EA and the combined org. layers were washed with water and brine, dried over Mg504 and concentrated under reduced pressure. The title compound was obtained, after purificationby CC (Combiflash; Hept/EA 0:1 to 1:0), as a yellow oil (108 mg; 62% yield). M53 (ESI, mlz): 457.10 [M+H+]; tR = 0.73 mm.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 198211-38-0, its application will become more common.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; CREN, Sylvaine; FRIEDLI, Astrid; RUEEDI, Georg; ZUMBRUNN, Cornelia; (200 pag.)WO2016/59097; (2016); A1;,
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Synthetic Route of 4424-80-0,Some common heterocyclic compound, 4424-80-0, name is 4,5-Dihydro-1H-benzo[b]azepin-2(3H)-one, molecular formula is C10H11NO, 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 Production of 2,3,4,5-tetrahydro-1H-benzo[b]azepine Lithium aluminum hydride (100 mg) was suspended in tetrahydrofuran (10 mL), 1,3,4,5-tetrahydrobenzo[b]azepin-2-one (245 mg) was added under ice-cooling by small portions. After heating under reflux for 5.5 hrs, water (0.1 mL), 15% aqueous sodium hydroxide (0.1 mL) and water (0.3 mL) were successively added under ice-cooling, and the mixture was stirred at room temperature. The mixture was dried over anhydrous sodium sulfate, and concentrated to give the title compound (301.6 mg) as a yellow oil.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4,5-Dihydro-1H-benzo[b]azepin-2(3H)-one, its application will become more common.

Reference:
Patent; Japan Tobacco Inc.; US2008/64871; (2008); A1;,
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Synthetic Route of 16375-88-5,Some common heterocyclic compound, 16375-88-5, name is N-(4-(Hydroxymethyl)phenyl)acetamide, molecular formula is C9H11NO2, 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: Bismuth vanadate (32.3 mg, 100 mmol) was added to a Schlenkflask containing benzyl alcohol stock solution (1 mL, 0.1 mmol inacetonitrile) and acetonitrile (9 mL). The mixture was left to stirfor 30 min to disperse the catalyst under a dioxygen atmospherevia a balloon. The mixture was then irradiated with a 30W blueLED array at a distance of 2 cmwith an irradiance of 245mWcm2.The mixture reached ca. 40 C by the end of the reaction and afterirradiation, the catalyst was removed using centrifugation at4000 rpm for 30 min. For GC analysis, 1 mL of supernatant wastaken and 1 lL injected. For NMR analysis, the supernatant wasreduced in volume using a rotary evaporator at 65 mbar at 20 C,and the residue dissolved in d6-DMSO containing maleic acid asan internal standard.

The synthetic route of 16375-88-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Unsworth, Christopher A.; Coulson, Ben; Chechik, Victor; Douthwaite, Richard E.; Journal of Catalysis; vol. 354; (2017); p. 152 – 159;,
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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. 2675-89-0, name is 2-Chloro-N,N-dimethylacetamide, A new synthetic method of this compound is introduced below., HPLC of Formula: C4H8ClNO

A solution of 4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-lH-pyrazole (0.8 g, 4.1 mmol), cesium carbonate (2.0 g, 6.2 mmol), and 2-chloro-N,N-dimethylacetamide (0.47 rnL, 4.5 mmol) in DMF (14 mL) was heated in a microwave at 900C for 1 hr. The crude reaction mixtures were then diluted with water (300 mL) and extracted with ethyl acetate (3 x 50 mL). Product was purified by silica gel column using DCM/EtOAc/MeOH (8/1.5/0.5) as eluent to provide N,N-dimethyl-2-(4-(4,4,5 ,5-tetramethyl- 1 ,3 ,2-dioxaborolan-2-yl)- 1 H-pyrazol- 1 – yl)acetamide (1.3 g) as a light yellow oil. ESI-MS:m/z 280.3 (M+H)+.

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; TAKEDA PHARMACEUTICAL COMPANY LIMITED; BRESSI, Jerome, C.; CHU, Shaosong; ERICKSON, Philip; KOMANDLA, Mallareddy; KWOK, Lily; LAWSON, John, D.; STAFFORD, Jeffrey, A.; WALLACE, Michael, B.; ZHANG, Zhiyuan; DAS, Sanjib; WO2010/19899; (2010); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics