Month: September 2021

Application of 121492-06-6,Some common heterocyclic compound, 121492-06-6, name is N-Boc-(2-Aminoethyl)-N-methylamine, molecular formula is C8H18N2O2, 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 mixture of tert-butyl 2-aminoethyl(methyl)carbamate (17.68 mg, 0.101 mmol), Hunig’sBase (0.053 mL, 0.304 mmol) and DMAP (1.240 mg, 10.15 muiotaetaomicron) in DCM (1 mL) was added methyl 4-((lR,3aS,5aR,5bR,7aR,l laS,l lbR,13aR,13bR)-3a- (chlorocarbonyl)-5a,5b,8,8,l la-pentamethyl-l-(prop-l-en-2-yl)- 2,3,3a,4,5,5a,5b,6,7,7a,8,l l,l la,l lb,12,13,13a,13b-octadecahydro-lH- cyclopenta[a]chrysen-9-yl)benzoate (60 mg, 0.101 mmol) in DCM (1 mL). The reaction mixture was stirred for 1 hour. LCMS indicated the formation of desired product. The reaction mixture was quenched with distilled water, extracted with DCM (3 x 3 mL). All the extracts were combined, dried over sodium sulfate, filtered and concentrated under reduced pressure to provide the desired product as white solid (65 mg, 88%). LCMS: m/e 729.61 (M+H)+, 2.72 min (method 1).

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

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; REGUEIRO-REN, Alicia; LIU, Zheng; SWIDORSKI, Jacob; MEANWELL, Nicholas A.; SIT, Sing-Yuen; CHEN, Jie; CHEN, Yan; SIN, Ny; WO2011/153319; (2011); A1;,
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Synthetic Route of 116861-31-5, These common heterocyclic compound, 116861-31-5, name is tert-Butyl (3-chloropropyl)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.

EXAMPLE 1 5-[(tert-butoxy)carbonyl]amino-2-ethoxycarbonyl-pentanoic acid ethyl ester (I: R1 =R2 =Et; R=–(CH2)3 –NHY; Y=Boc) Sodium metal (2.5 g, 0.1 mol) is dissolved in absolute ethyl alcohol (70 ml) while keeping the reaction mixture under nitrogen atmosphere. The temperature is then brought to 60 C. and malonic acid di-ethyl ester (35 g, 0.2 mol) is gradually dripped in. N-[(tert-butoxy)carbonyl]-3-chloro-propylamine (12.2 g, 0.1 mol) is gradually added, at room temperature, to the resulting solution. Stirring is continued at room temperature for 2 hours and then at the reflux temperature for 6 hours. The reaction mixture is poured into an ethyl acetate/water (1/1, v/v) mixture (400 ml) and the organic phase is recovered, washed several times with water and dried over MgSO4. The organic solvent is removed under vacuum (0.5 mBar) at 100 C., yielding a pale yellow oil (27.7 g, 87%), N.M.R. analysis of this product confirms the assigned structure.

The synthetic route of 116861-31-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Eniricerche S.p.A.; Sclavo S.p.A.; US4914226; (1990); A;,
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Application of 2675-89-0, 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 2675-89-0 as follows.

To a suspension of NaH (344 mg, 60% dispersion in mineral oil) in THF (17 mL) was added allyl alcohol (2) (500 mg, 8.6 mmol) at 0 C. After 1 h at the same temperature, chloroacetamide 1 (0.97 mL, 9.5 mmol) was added and the mixture was stirred for 24 h. The mixture was quenched with saturated aqueous NH4Cl and concentrated at reduced pressure. The resulting residue was dissolved in EtOAc and washed with water and brine. The organic layer was dried over anhydrous MgSO4 and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (hexanes/EtOAc, 3:1) to give 6a (1.05 g, pale yellow oil) in 85% yield.

According to the analysis of related databases, 2675-89-0, the application of this compound in the production field has become more and more popular.

Reference:
Article; Yun, Jeong In; Kim, Hyoung Rae; Kim, Sang Kyum; Kim, Deukjoon; Lee, Jongkook; Tetrahedron; vol. 68; 4; (2012); p. 1177 – 1184;,
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Synthetic Route of 16982-21-1, 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. 16982-21-1 name is Ethyl 2-amino-2-thioxoacetate, 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.

To a 3-neck, 200 mL round bottom flask under nitrogen was added 3-bromo-2-oxopropanoic acid (5 g, 30 mmol) and anhydrous 1,4-dioxane (50 mL). To this mixture was added ethyl 2-amino-2-thioxoacetate (4.1 g, 31 mmol) and the mixture heated at 50 C. for 1.5 h. The reaction was concentrated to dryness, the residue was dissolved in saturated aqueous NaHCO3 (100 mL) and water (100 mL), and the aqueous solution extracted with ethyl acetate (4 ×100 mL). The aqueous layer was acidified to pH 2 with concentrated HCl. After precipitate formation (20 min) the aqueous mixture was extracted with ethyl acetate (3×100 mL). The combined organic layers were dried over anhydrous sodium sulfate and concentrated to dryness to give the title compound as a red solid, which was used in next step without further purification.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Ethyl 2-amino-2-thioxoacetate, and friends who are interested can also refer to it.

Reference:
Patent; Janssen Pharmaceutica NV; Goldberg, Steven; McClure, Kelly; Tanis, Virginia M.; Fennema, Elizabeth G.; Lebsack, Alec D.; Martin, Connor L.; Venkatesan, Hariharan; Xue, Xiaohua; Woods, Craig R.; (531 pag.)US2017/313691; (2017); A1;,
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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. 71026-66-9, name is tert-Butyl (4-aminophenyl)carbamate, A new synthetic method of this compound is introduced below., name: tert-Butyl (4-aminophenyl)carbamate

2,4-dichloro-5-nitropyrimidine (190 mg, 0.98 mmol) 6 mL of 1,4-dioxane was added,Placed in a 25 mL round bottom flask, Stirred at room temperature,(4-aminophenyl)Tert-butyl carbamate(200 mg, 0.96 mmol),N,N-diisopropylethylamine (137 mg, 1.06 mmol)Dissolved in 4 mL of 1,4-dioxane, Slowly added dropwise to the above reaction solution,After the addition was continued, the mixture was stirred at room temperature for about 1 hour,TLC to monitor the complete conversion of the reaction.Rotary Evaporation In addition to solvent,The crude product was separated by silica gel column chromatography (petroleum ether / ethyl acetate = 10: 1, v / v)To give 301 mg of tert-butyl (4- (2-chloro-5-nitropyrimidine-4-amino) phenyl)carbamate as an orange solid in 82% yield.

The synthetic route of 71026-66-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; East China University of Science and Technology; LI, HONGLIN; XU, YUFANG; CHEN, ZHUO; ZHAO, ZHENJIANG; LU, JIANKUN; SUN, DEHENG; YANG, YU; ZHOU, WEI; (29 pag.)CN106467540; (2017); A;,
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Electric Literature of 7150-72-3, A common heterocyclic compound, 7150-72-3, name is tert-Butyl vinylcarbamate, molecular formula is C7H13NO2, 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: A 10 mL round-bottomed flask equipped with a rubber septum and a magnetic stir bar was charged with 1 (1.0 equiv), 2 (2.5 equiv), 3 (2.0 equiv), and fac-Ir(ppy)3 (0.01 equiv). The flask was evacuated and backfilled 3 times with N2. DMSO was then added with syringe under N2. The mixture was then irradiated by white LED strips. After completion of the reaction (6 h, as judged by TLC analysis), the mixture was poured into a separatory funnel containing sat. aq NaHCO3 (20mL) and EtOAc (20 mL). After extraction with EtOAc, the organic layer was separated, dried (Na2SO4), and concentrated under reduced pressure after filtration. The crude product was purified by flash chromatography on silica gel to afford the desired product 4.

The synthetic route of 7150-72-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; An, Xiao-De; Yu, Shouyun; Synthesis; vol. 50; 17; (2018); p. 3387 – 3394;,
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Synthetic Route of 118753-70-1,Some common heterocyclic compound, 118753-70-1, name is tert-Butyl bis(2-chloroethyl)carbamate, molecular formula is C9H17Cl2NO2, 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 solution containing bis(2-chloroethyl)-N-BOC amine (described in US Patent 5,661, 163) (8.15 g, 33.67 mmol), 3,4-dichlorophenylacetonitrile (5.05 g, 27.17 mmol), and DMSO (50 mL) was stirred at RT and solid cesium carbonate (17.6 g, 54.02 mmol) was added (in portions) over 10 minutes. After 20 h, additional cesium carbonate (1.7 g, ) was added, and the mixture stirred for an additional 72 h. The mixture was partitioned between water and EtOAc, the aq. layer was removed, and the organic layer washed successively with additional water,0.1M aq. HCl (2X), sat. aq.NaHC03, and brine. The organic layer was dried, filtered, concentrated, and the residue triturated (3: 1 hexane/ethyl acetate) to give the title compound as an off-white solid, m. p.142-145 C. MS m/z 255. 1H NMR (CDC13) 6 7.55 (d,1H), 7.49 (d, 1H), 7.32(m,1H), 4.3 (br d, 2H), 3.18 (br t, 2H), 2.07 (d, 2H), 1.89(m, 2H), 1.48 (s, 9H).

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 bis(2-chloroethyl)carbamate, its application will become more common.

Reference:
Patent; ASTRAZENECA AB; WO2004/20411; (2004); A1;,
Amide – Wikipedia,
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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. 72505-21-6, name is 4-(Trifluoromethyl)thiobenzamide, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 4-(Trifluoromethyl)thiobenzamide

4- (Trifluoromethyl) thiobenzamide (20.5 g, 0.1 mol) was dissolved in tetrahydrofuran (300 [UN)] at room temperature, and then methyl [2-CHLOROACETOACETATE] (12.2 [UN,] 0.1 mol) was added slowly for about 20 minutes therein while stirring. After completion of addition, the mixture was stirred again at room temperature for 30 minutes, and then the mixture was heated and refluxed at 78 to 80 C for 12 hours. After completion of the reaction, the reaction mixture was cooled to room temperature. Subsequently, 50% aqueous solution of sodium hydroxide [(150 NE)] was added and stirred for 20 minutes. The resultant organic layer was separated by extraction with ethyl acetate, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure to thereby yield 28.8 g of the title compound (yield: 95. 6%). ‘H-NMR (300 MHz, [CDCI3)] : 8.01 (d, 2H, [J =] 8.4 Hz), 7.64 (d, 2H, [J= 8. 3] Hz), 3. 84 [(S, 3H),] 2. [73] (s, [3H).]

According to the analysis of related databases, 72505-21-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; KANG, Heonjoong; HAM, Jungyeob; WO2003/106442; (2003); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 7223-30-5,Some common heterocyclic compound, 7223-30-5, name is 3-Phenylpropiolamide, molecular formula is C9H7NO, 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: A mixture of alkynes 1 (0.5 mmol), 2 (0.6 mmol), palladium chloride (3.2 mg, 3 mol %), ionic liquid (0.5 mL), HX (0.25 mL) in a test tube (10 mL) equipped with a magnetic stirring bar. The mixture was stirred under the atmosphere of air at room temperature. After the reaction was completed, 10 mL ethyl acetate (3×10 mL) was added into the tube. The combined organic layers were washed with brine to neutral, dried over MgSO4, and concentrated in vacuum. Purification of the residue on a preparative TLC afforded the desired products. Residual ionic liquid obtained after the workup was stirred with diethyl ether (2×10 mL) for 15 min, and the ethereal layer was decanted. The ionic liquid was then directly used for the next runs without further dry and reused for up to five runs.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Phenylpropiolamide, its application will become more common.

Reference:
Article; Li, Jianxiao; Yang, Shaorong; Wu, Wanqing; Qi, Chaorong; Deng, Zhongxian; Jiang, Huanfeng; Tetrahedron; vol. 70; 7; (2014); p. 1516 – 1523;,
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Reference of 1195768-19-4, A common heterocyclic compound, 1195768-19-4, name is Methyl 3-(2,6-difluorophenylsulfonamido)-2-fluorobenzoate, molecular formula is C14H10F3NO4S, 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.

Step B: N-{3-[(2-chloro-4-pyrimidinyl)acetyl]-2-fluorophenyl}-2,6- difluorobenzenesulfonamide Methyl 3-{[(2,6-difluorophenyl)sulfonyl]amino}-2-fluorobenzoate (490 g, 1 equiv.), prepared generally in accordance with Step A, above, was dissolved in THF (2.45 L, 5 vols) and stirred and cooled to 0-3 C. 1M lithium bis(trimethylsilyl)amide in THF (5.25 L, 3.7 equiv.) solution was charged to the reaction mixture followed addition of 2- chloro-4-methylpyrimidine (238 g, 1.3 equiv.) in THF (2.45 L, 5 vols). The reaction was then stirred for 1 hr. The reaction was quenched with 4.5M HC1 (3.92 L, 8 vols). The aqueous layer (bootom layer) was removed and discarded. The organic layer was concentrated under reduced pressure to ~2L. IP AC (isopropyl acetate) (2.45L) was added to the reaction mixture which was then concentrated to ~2L. IP AC (0.5L) and MTBE (2.45 L) was added and stirred overnight under N2. The solids were filtered. The solids and mother filtrate added back together and stirred for several hours. The solids were filtered and washed with MTBE (~5 vol). The solids were placed in vacuum oven at 50 C overnight. The solids were dried in vacuum oven at 30 C over weekend to obtain N-{3- [(2-chloro-4-pyrimidinyl)acetyl]-2-fluorophenyl}-2,6-difluorobenzenesulfonamide (479 g, 72%).

The synthetic route of 1195768-19-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; GRESHOCK, Joel David; HOOS, Axel; WO2015/87279; (2015); A1;,
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Amide – an overview | ScienceDirect Topics