Month: January 2021

These common heterocyclic compound, 337463-88-4, name is 6-Bromo-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one, 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. SDS of cas: 337463-88-4

(d) 6-((¡ê)-Styryl)-4H-pyrido[3,2-¡ê>][1 ,4]oxazin-3-one; 6-Bromo-4H-pyrido[3,2-b][1 ,4]oxazin-3-one (6.0 g, 26.3 mmole) and trans-2- phenylvinylboronic acid (3.9 g, 26.3 mmole) were dissolved in 1 ,4-dioxane (150 mL) and the solution was degassed with argon. (Ph3P)4Pd (230 mg, 0.2 mmole) was added, followed by a solution of potassium carbonate (6.9 g, 50 mmole) in H2O (20 mL). The reaction was heated at reflux under argon overnight, then was cooled to room temperature and diluted with EtOAc (200 mL). The solution was washed sequentially with H2O and brine, dried (Na2SC>4), and concentrated in vacuo. The solid residue was purified by flash chromatography on silica gel (5-10% EtOAc/CHCl3) to afford a solid (2.5 g, 38%): MS (ES) m/z253.0 (M + H)+.

The synthetic route of 6-Bromo-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; WO2006/81179; (2006); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 88829-82-7, 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. 88829-82-7 name is tert-Butyl (8-aminooctyl)carbamate, 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.

General procedure 2. Starting compound III: S-Methyl N-cyano-N’-4-pyridylisothiourea. Starting compound IV: 8-t-Butoxycarbonylaminooctylamine. Purification: General procedure. 13C NMR (CDCl3) delta: 157.3, 155.5, 149.8, 146.1, 116.4, 114.5, 77.2, 41.7, 29.4, 28.6, 28.6, 28.2, 26.1, 26.0.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, tert-Butyl (8-aminooctyl)carbamate, and friends who are interested can also refer to it.

Reference:
Patent; Leo Pharmaceutical Products, Ltd. A/S; US6346520; (2002); B1;,
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. 24036-52-0, name is 6-Bromo-2H-1,4-benzoxazin-3(4H)-one, A new synthetic method of this compound is introduced below., Recommanded Product: 6-Bromo-2H-1,4-benzoxazin-3(4H)-one

Step II: To a stirred solution of 6-bromo-2H-1,4-benzoxazin-3(4H)-one (10 g, 43.85 mmol) in THF (25 ml) was added 1.0 M borane-tetrahydrofuran complex in THF (153.5 ml, 153.48 mmol) and refluxed for 14 h. The reaction mixture was cooled to room temperature, quenched with methanol (50 ml) and concentrated under reduced pressure. The resulting residue was taken in ethyl acetate (100 ml), washed with aqueous saturated sodium bicarbonate solution (100 ml), water (100 ml), brine (100 ml), dried over sodium sulphate, concentrated and purified by silica gel column chromatography (5% ethyl acetate in hexane) to provide 6-bromo-3,4-dihydro-2H- benzop^oxazine (8.5 g).

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; NOVARTIS AG; BEBERNITZ, Gregory Raymond; BHOSALE, Sandeep Bhausaheb; BHUNIYA, Debnath; HAJARE, Atul Kashinath; MENGAWADE, Tanaji; MUKHOPADHYAY, Partha P.; PALLE, P. Venkata; REDDY, Dumbala Srinivas; WO2010/128152; (2010); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 4815-28-5,Some common heterocyclic compound, 4815-28-5, name is 2-Amino-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxamide, molecular formula is C9H12N2OS, 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 492-(2-(3-(trifluoromethyl)-4,5,6,7-tetrahydroindazole-1-yl)propanamido)-4,5,6,7- tetrahydrobenzorithiophene-3-carboxamide a) 2-(3-chloropropanamido)-4,5,6,7-tetrahydrobenzo[]thiophene-3-carboxamide2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide (250 mg, 1.28 mmol) and triethylamine (0.18 ml_, 1.28 mmol) were stirred in DCM (5 ml_). 3-chloropropionylchloride (162 mg, 1.28 mmol) was added dropwise under a nitrogen atmosphere. Stirring was continued for 2 h. 2 M HCI (20 ml_) was added and the reaction mixture extracted into DCM (3 x 50 ml_), The combined DCM layers were washed with brine, dried over MgSO4, filtered and the solvent removed in vacuo to give the desired product as a yellow solid (290 mg, 1.01 mmol, 79 %).1 H NMR (400MHz, CDCI3): delta 1.86 (m, 4H), 2.72 (m,4H), 2.91 (t,2H), 3.86 (t, 2H), 5.73 (s, 2H), 12.1 (s,1 H).

The synthetic route of 4815-28-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; N.V. ORGANON; WO2008/3452; (2008); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 104863-65-2, 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 104863-65-2 as follows.

A solution of 140 mL (0.18 mol) of 1.3M sec-butyl lithium in cyclohexane was added slowly to N-tert-butoxycarbonyl-3-methoxy-2-methylaniline (21.3 g, 0.09 mol) in 250 mL of THF keeping the temperature below -40 C. with a dry ice-ethanol bath. The bath was removed and the temperature allowed to warm to 0 C. and then the bath replaced. After the temperature had cooled to -60 C., 18.5 g (0.18 mol) of N-methoxy-N-methylpropanamide in an equal volume of THF was added dropwise. The reaction mixture was stirred 5 minutes, the cooling bath removed and stirred an additional 18 hours. It was then poured into a mixture of 300 mL of ether and 400 mL of 0.5N HCl. The organic layer was separated, washed with water, brine, dried over MgSO4, and concentrated at reduced pressure to give 25.5 g of a crude of 1-[2-(tert-butoxycarbonylamino)-6-methoxyphenyl]-2-butanone. This material was dissolved in 250 mL of methylene chloride and 50 mL of trifluoroacetic acid and stirred for a total of 17 hours. The mixture was concentrated at reduced pressure and ethyl acetate and water added to the remaining oil. The ethyl acetate was separated, washed with brine, dried (MgSO4) and concentrated. The residue was chromatographed three times on silica eluting with 20% EtOAc/hexane to give 13.9 g of 2-ethyl-4-methoxy-1H-indole.

According to the analysis of related databases, 104863-65-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Harper, Richard Waltz; Lin, Ho-Shen; Richett, Michael Enrico; US2004/29948; (2004); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Related Products of 42137-88-2,Some common heterocyclic compound, 42137-88-2, name is N,N-Bis(2-chloroethyl)-4-methylbenzenesulfonamide, molecular formula is C11H15Cl2NO2S, 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 suspension of N-(4-(aminomethyl)-3-(trifluoromethyl)phenyl)-3-(imidazo[1,2-b]pyridazin-3-ylethynyl)-4-methylbenzamide (If) (3.22 g, 7.18 mmol) in diisopropylethylamine (2.49 mL, 14.32 mmol) was charged N,N-bis(2-chloroethyl)-4-toluenesulfonamide (2.13 g, 7.18 mmol). The reaction mixture was heated to reflux (-130 C.) for 36 h. The progress of the reaction was monitored by TLC. The reaction mixture was transferred into a mixture of deionized water (6 mL), ice (20 g), potassium carbonate (7 g), and dichloromethane (25 mL). The layers were separated and the aqueous layer extracted with dichloromethane (3*5 mL). The combined organic layers were treated with activated charcoal, dried over magnesium sulfate, and then evaporated to dryness under vacuum to give the product 3-(imidazo[1,2-b]pyridazin-3-ylethynyl)-4-methyl-N-(4-((4-tosylpiperazin-1-yl)methyl)-3-(trifluoromethyl)phenyl)benzamide (Ig) (2.2 g).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route N,N-Bis(2-chloroethyl)-4-methylbenzenesulfonamide, its application will become more common.

Reference:
Patent; Apicore, LLC; Kovi, Ravishanker; Kannapan, Jayaraman; Thakor, Sanjay F.; Patel, Rajesh A; US2014/343282; (2014); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 191170-76-0,Some common heterocyclic compound, 191170-76-0, name is Benzyl 4-bromophenethylcarbamate, molecular formula is C16H16BrNO2, 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 of intermediate 3.3 (2g, 6 mmol, 1 eq.) and intermediate 3.10 (2g, 6 mmol, 1 eq.) in DMF is purged with Ar2 for 10 min. Pd(dppf)Cl2 (122 mg, 0.15 mmol, 0.4 eq.) and 8 mL 2N Na2Ctheta3/H2O are then added and the resulting reaction mixture is sealed in a tube and heated to 120 0C in a microwave oven for 30 min. The reaction mixture is diluted with EtOAc and washed with water and brine. The organic layer is dried over Na2SO4, filtered and concentrated to give a dark oil that is purified by flash column (40%~60% EtOAc/hexanes, 40 g column) yielding intermediate 3.11 as a light greenish oil (2 g, 4.3 mmol, 72%).

The synthetic route of 191170-76-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BOEHRINGER INGELHEIM PHARMA GMBH & CO. KG; WO2009/52078; (2009); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 41921-63-5,Some common heterocyclic compound, 41921-63-5, name is 4,5-Dihydro-1H-benzo[d][1,3]diazepin-2(3H)-one, molecular formula is C9H10N2O, 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.

d) 7-Bromo-1 ,3,4,5-tetrahydro-2H-1 ,3-benzodiazepin-2-one.To a solution of 1 ,3,4,5-tetrahydro-2H-1 ,3-benzodiazepin-2-one (55 mg, 0.340 mmol) in dry dimethylformamide (3 mL) was added N-bromosuccinimide (67 mg, 0.374 mmol) in one portion. After 30 min, the reaction mixture was quenched with water (5 mL) and extracted with three 10 mL portions of ethyl acetate. The combined extracts were dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography (7% methanol in dichloromethane) to give 55 mg (67%,) of 7-bromo-1 ,3,4,5-tetrahydro-2H-1 ,3- EPO benzodiazepin-2-one as a white solid. ESMS [M+H]+: 241.0.

The synthetic route of 41921-63-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2006/113432; (2006); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Some common heterocyclic compound, 185693-02-1, name is tert-Butyl hexahydropyrrolo[3,4-b]pyrrole-1(2H)-carboxylate, molecular formula is C11H20N2O2, 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: C11H20N2O2

The product from Step 2 (150mg, 0.5mmol), tert-butyl hexahydropyrrolo[3,4-b]pyrrole-1-carboxylate (100mg, 0.5mmol), and anhydrous potassium carbonate (128mg, 0.9mmol) were suspended in N,N-dimethylformamide (3.0mL). The mixture was reacted at 80C for 1h. The reaction mixture was poured into 20ml ice water, and extracted with ethyl acetate. The organic phases were combined, washed with a saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and filtered. The filtrate was evaporated under reduced pressure to remove the solvent to produce a crude product. The crude product was purified with a silica gel column chromatography to produce the title compound (110mg). ESI-MS (m/z): 455.2 [M + H]+

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 185693-02-1, its application will become more common.

Reference:
Patent; Sichuan Kelun-Biotech Biopharmaceutical Co., Ltd.; CAI, Jiaqiang; YU, Nan; ZENG, Hong; SONG, Hongmei; QING, Yan; SONG, Shuai; DENG, Hanwen; TANG, Zujian; DUAN, Xiaofan; HUANG, Haitao; YE, Hong; LIU, Gang; WANG, Lichun; WANG, Jingyi; (81 pag.)EP3511332; (2019); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 67442-07-3, A common heterocyclic compound, 67442-07-3, name is 2-Chloro-N-methoxy-N-methylacetamide, molecular formula is C4H8ClNO2, 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.

Under nitrogen protection, 1340.5g of intermediate was taken, dissolved in 200mL anhydrous THF, the reaction system was cooled to -15¡ã, and 13g of THF solution of 13g isopropylmagnesium chloride was added dropwise. During the dropwise addition, the reaction temperature was controlled at -5¡ã. After the completion of the dropwise addition, the reaction was continued for 1 h, and then 60 g of a solution of 15 g of 2-chloro-N-methoxy-N-methylacetamide in THF was added dropwise thereto, and the reaction temperature was controlled not to exceed -5¡ã during the dropwise addition. After the end of the addition, the temperature of the system was raised to -5-0 ¡ã, and after the reaction was completed, the reaction was quenched by the addition of 2N hydrochloric acid at 0 ¡ã, and ethyl acetate (200 mL) was added, and the mixture was separated. , filtration, solvent recovery under reduced pressure, residue,With methanol:Water = 10:1 recrystallized to give a white solid, 27 g, yield 76percent.

The synthetic route of 67442-07-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Jiangsu Engineering Polytechnic College; Feng Chengliang; Yao Wenjin; Yan Bin; (12 pag.)CN109678686; (2019); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics