Month: March 2021

Some common heterocyclic compound, 153248-46-5, name is [1-[(Boc-amino)methyl]cyclopropyl]methanol, molecular formula is C10H19NO3, 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: C10H19NO3

To a solution of PPh3 (244 mg, 0.90 mmol) in anhydrous tetrahydrofuran (10 mL) was added DIAD (188 mg, 0.90 mmol) by syringe at 05 C, followed by a solution of tert-butyl (1 -(hydroxymethyl)cyclopropyl)methylcarbamate (110-13) (178 mg, 0.90 mmol) in anhydrous tetrahydrofuran (5 mL). The resulting mixture was poured into a solution of compound 308-7 (100 mg, 0.30 mmol) in anhydrous tetrahydrofuran (5 mL) at ambient temperature and stirred for 10 mm. The reaction mixture was quenched with water and extracted with ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous sodium sulfate and evaporated in vacuo. The crude product was purified by column chromatography (dichloromethane/ethyl acetate: 5/1) to afford the title compound 309-17 as a yellow solid (100 mg, crude). LCMS: 522.3 [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 153248-46-5, its application will become more common.

Reference:
Patent; PHARMAENGINE, INC.; CAI, Xiong; QIAN, Changgeng; WANG, Yanong Daniel; (98 pag.)WO2017/132928; (2017); A1;,
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Synthetic Route of 1746-77-6,Some common heterocyclic compound, 1746-77-6, name is Isopropyl carbamate, molecular formula is C4H9NO2, 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.

Isopropyl carbamate (30 g, 291 mmol, available from TCI) was charged to a 3 L Lara vessel and dry Tetrahydrofuran (THF) (150 ml) added. (2E)-2-butenoyl chloride (31.2 ml, 326 mmol, available from Aldrich) was added under nitrogen and the jacket cooled to -30 C. When the solution temperature reached -17 C. 1M Lithium tert-butoxide (655 ml, 655 mmol) was added by peristaltic pump over 2 hours, keeping the reaction temperature between -10 C. and -18 C. Once the addition was complete the mixture was complete the mixture was stirred for 30 mins and brought to 0 C. Diethyl ether (450 ml) and 1M HCl (375 ml) were added and the mixture brought to 20 C. with vigorous stirring. The stirring was stopped, the layers allowed to separate and the aqueous layer run off. Brine (375 ml) was added and the mixture stirred vigorously. The stirring was stopped, the layers allowed to separate and the aqueous layer run off. The organic layer was dried (magnesium sulfate), filtered and evaporated to a brown oil (60 g). The mixture was loaded on to a 40+M Biotage silica column and eluted with DCM:ethyl acetate (1:1 to 0:1, 10 CV). The product containing fractions were evaporated to dryness and loaded on to a 1500 g Redisep Isco silica column and eluted with a gradient of 0 to 40% ethyl acetate in cyclohexane. The clean, product containing fractions were evaporated to an off white solid (15.41 g). LCMS (Method C): Rt=0.68, MH+=172

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

Reference:
Patent; Demont, Emmanuel Hubert; Garton, Neil Stuart; Gosmini, Romain Luc Marie; Hayhow, Thomas George Christopher; Seal, Jonathan; Wilson, David Matthew; Woodrow, Michael David; US2012/208798; (2012); A1;,
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Synthetic Route of 16982-21-1, A common heterocyclic compound, 16982-21-1, name is Ethyl 2-amino-2-thioxoacetate, molecular formula is C4H7NO2S, 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.

4B. Ethyl 4-phenylthiazole-2-carboxylate A mixture of 2-bromo-1-phenylethanone (1.790 g, 8.99 mmol) and ethyl 2-amino-2-thioxoacetate (Example 4A, 1.20 g, 9.01 mmol) in benzene (80 mL) and ethanol (10 mL) was stirred at room temperature for 18 h. The mixture was heated at 80 C. for 1 h. The solvent was evaporated under reduced pressure and the residue was partitioned between ethyl acetate (300 mL) and saturated aqueous sodium bicarbonate (100 mL). The organic phase was washed with brine, dried over anhydrous magnesium sulfate and concentrated in vacuo. The residual clear oil was chromatographed on silica gel (4*10 cm, elution toluene-ethyl acetate 0-2-4%) and gave a yellow oil (1.588 g). This was distilled in vacuo (bp: 105-115 C./0.1 torr, bulb to bulb distillation, air bath temperature) to provide the title material (1.409 g, 67%) as a pale yellow syrup which solidified to an almost colorless solid upon standing. LC (Method C): 2.009 min. HRMS (ESI) calcd for C12H12NO2S [M+H]+ m/z 234.0583. found 234.0597. 1H NMR (CDCl3, 400 MHz) delta ppm: 1.48 (t, J=7.2 Hz, 3H), 4.52 (q, J=7.2 Hz, 2H), 7.35-7.49 (m, 3H), 7.75 (s, 1H), 7.93-8.00 (m, 2H).

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; Kornacker, Michael G.; Mapelli, Claudio; Riexinger, Douglas James; US2013/289238; (2013); A1;,
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Reference of 35303-76-5, The chemical industry reduces the impact on the environment during synthesis 35303-76-5, name is 4-(2-Aminoethyl)benzenesulfonamide, I believe this compound will play a more active role in future production and life.

A THF solution (20 ml) of 4- (4-isocyanatobutyl) benzene (1.71 mmol) and 4- (2-aminoethyl) benzenesulfonamide (20 ml) was stirred at 40-45 ¡ã C for 24 hours. The next day, the completion of the reaction was confirmed by TLC. The solvent was distilled off and ammonium chloride (100 ml), water (50 ml) and ethyl acetate (100 ml) were added to the remaining residue. The organic layer was treated with brine and dried over sodium sulfate. The solvent was distilled off and the resulting concentrate was adsorbed onto silica gel using methylene chloride. The mixture was purified by column chromatography using ethyl acetate in hexane to give the title compound.

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, 4-(2-Aminoethyl)benzenesulfonamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; The Industry & Academic Cooperation in Chungnam National University (IAC); Jung, Sang-Hun; Woo, Sun-Hee; Kim, Sang- Kyum; Jeon, Eun-Seok; Lee, Yu-Jung; Meunikam, Manoj; Jalani, Hiteshkumar; Sharma, Niti; (205 pag.)KR2016/108281; (2016); A;,
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Application of 123664-84-6, 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 123664-84-6 as follows.

(1) In 100 ml of anhydrous methylene chloride were dissolved 10 g of 3-methylsulfonylamino-4-phenoxyanisole and 2.81 g of acetyl chloride. Thereto was added 9.1 g of aluminum chloride in 5 minutes with ice-cooling. The mixture was stirred for 1 hour at 20-25 C. The reaction mixture was introduced into 100 ml of ice water. The resulting organic layer was separated, washed with water and a saturated aqueous sodium chloride solution in this order, and dried with anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue was recrystallized from isopropyl alcohol to obtain 9.83 g (yield: 86%) of methyl 4-methylsulfonylamino-2-methoxy-5-phenoxyphenyl ketone having a melting point of 108.5-110 C. IR (KBr) cm-1: 3300, 1640, 1600, 1490, 1330, 1210, 1155

According to the analysis of related databases, 123664-84-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Toyama Chemical Company, Ltd.; US4954518; (1990); A;,
Amide – Wikipedia,
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Reference of 6292-59-7,Some common heterocyclic compound, 6292-59-7, name is 4-(tert-Butyl)benzenesulfonamide, molecular formula is C10H15NO2S, 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: 2.2 General procedure: 4-methyl-N-phenylbenzenesulfonamide (3a) A 25 mL oven-dried reaction vessel was charged with Pd(TFA)2 (2.3 mg, 0.01 mmol), 1,10-phenanthroline (3.6 mg, 0.02 mmol), p-toluene sulfonamide (1a, 34.2 mg, 0.2 mmol), cyclohexanone (2a, 32 muL, 0.3 mmol). The reaction vessel was flushed with oxygen three times and then sealed. Toluene (0.7 mL) was added by syringe and the resulting solution was stirred at 140 ¡ãC for 40 h. After cooling to room temperature, the volatiles were removed under vacuum and the residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate = 4:1) to give the corresponding product 3a (39.9 mg) as white solid in 81percent yield.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-(tert-Butyl)benzenesulfonamide, its application will become more common.

Reference:
Article; Cao, Xiangxiang; Bai, Yang; Xie, Yanjun; Deng, Guo-Jun; Journal of Molecular Catalysis A: Chemical; vol. 383-384; (2014); p. 94 – 100;,
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Electric Literature of 17641-08-6, 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 17641-08-6 as follows.

General procedure: A mixture of the key intermediate 13 (1.0 mmol), diverse 2-chloro-N-sbustituted acetamidederivatives 15 (1.0 mmol) and potassium carbonate (K2CO3) (0.15 g, 1.1 mmol) in 5.0 mL ofanhydrous ethanol was stirred and refluxed for 2.0-2.5 h. After the reaction was complete accordingto the TLC detection, the precipitate was filtered off and solvent was removed under reducedpressure and the residue was purified by column chromatography to give the target compounds inyields of 57-78%.

According to the analysis of related databases, 17641-08-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Zhao, Pei-Liang; Chen, Peng; Li, Qiu; Hu, Meng-Jin; Diao, Peng-Cheng; Pan, En-Shan; You, Wen-Wei; Bioorganic and Medicinal Chemistry Letters; vol. 26; 15; (2016); p. 3679 – 3683;,
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Related Products of 120157-96-2, 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. 120157-96-2, name is Methyl 4-(((tert-butoxycarbonyl)amino)methyl)benzoate, This compound has unique chemical properties. The synthetic route is as follows.

To a cold suspension of LiAlH4 (60 mg, 1.5 mmol) in ether (5 mL) at -78 C. was added dropwise a solution of methyl 4-(N-t-Boc-aminomethyl)benzoate (0.8 g, 3 mmol) in ether (5 mL) and the contents were allowed to warm-up to ambient temp. After 3 h, further amount of LiAlH4 (100 mg) was added and the reaction was continued at room temp for further 10 min. Excess LiAlH4 was destroyed with EtOAc followed by saturated ammonium chloride (1.0 mL), The solid precipitated was filtered and washed with ether. The filtrate was evaporated to give 4-(N-t-Boc-aminomethyl)benzyl alcohol (250 mg, 35%).

The chemical industry reduces the impact on the environment during synthesis Methyl 4-(((tert-butoxycarbonyl)amino)methyl)benzoate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Eli Lilly and Company; Wayne State University; University of Hawaii; US6680311; (2004); B1;,
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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 185693-02-1 as follows. Safety of tert-Butyl hexahydropyrrolo[3,4-b]pyrrole-1(2H)-carboxylate

To R20 (6.0 g, 28.26 mmol) in dichioromethane (200 mL) are added R21 (3.16 mL, 31.09 mmol) and acetic acid (1.62 mL, 28.26 mmol) and stirred for 1 h at r.t.. Sodiumtriacetoxyborohydride (9.46 g, 42.40 mmol) is added and stirred overnight at r.t.. The reaction mixture is diluted with dichloromethane and saturated sodium hydrogencarbonate solution. The organic layer is dried and concentrated in vacuo.Yield 100% m/z 303 [M+H]+, rt 1.34 mi LC-MS Method VOll SOl.

According to the analysis of related databases, 185693-02-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; GRAUERT, Matthias; ANDERSKEWITZ, Ralf; BIXENMANN, Achim; GRUNDL, Marc; HAEBEL, Peter Wilhelm; PAUTSCH, Alexander; (80 pag.)WO2016/16242; (2016); A1;,
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Synthetic Route of 111300-06-2,Some common heterocyclic compound, 111300-06-2, name is tert-Butyl (trans-4-hydroxycyclohexyl)carbamate, molecular formula is C11H21NO3, 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 frans-N-{4-[6-butyl-5-(4-cyclohexyloxy-phenyl)-pyridazin-3-yloxy]-cyclohexyl}- formamide in anhydrous THF at 0C may be treated with borane-THF complex in THF (1 M, excess). The reaction may be allowed to come to room temperature and may be monitored by LCMS until the reaction is complete. The reaction may be quenched with MeOH and the solvents may be removed under reduced pressure. The crude product may be purified by flash chromatography using with 1 – 5 % (2N N H3 in MeOH) in DCM to give frans-{4-[6-butyl-5-(4-cyclohexyloxy-phenyl)-pyridazin-3-yloxy]- cyclohexyl}-methyl-amine. The neutral amine may be treated with 2N HCI in diethyl ether and DCM.The volatiles may be removed under reduced pressure and the salt may be triturated with diethyl ether and filtered to provide the title compound. LCMS: m/z 439 [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 tert-Butyl (trans-4-hydroxycyclohexyl)carbamate, its application will become more common.

Reference:
Patent; TRANSTECH PHARMA, INC.; GOHIMUKKULA, Devi, Reddy; JONES, David; QABAJA, Ghassan; ZHU, Jeff, Jiqun; COOPER, Jeremy, T.; BANNER, William, Kenneth; SUNDERMANN, Kurt; BONDLELA, Muralidhar; RAO, Mohan; WANG, Pingzhen; GOWDA, Raju, Bore; ANDREWS, Robert, C.; GUPTA, Suparna; HARI, Anitha; WO2011/103091; (2011); A1;,
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