Tag: M.W=100-200

Adding some certain compound to certain chemical reactions, such as: 3984-14-3, name is N,N-Dimethylsulfamide, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 3984-14-3. 3984-14-3

Intermediate 3 1H-Indole-6-carboxamide, 2-bromo-3-cyclohexyl-N-[(dimethylamino)sulfonyl]-. 1,1′-Carbonyldiimidazole (1.17 g, 7.2 mmol) was added to a stirred solution of 2-bromo-3-cyclohexyl-1H-indole-6-carboxylic acid (2.03 g, 6.3 mmol) in THF (6 mL) at 22 C. The evolution of CO2 was instantaneous and when it slowed the solution was heated at 50 C. for 1 hr and then cooled to 22 C. N,N-Dimethylsulfamide (0.94 g, 7.56 mmol) was added followed by the dropwise addition of a solution of DBU (1.34 g ,8.8 mmol) in THF (4 mL). Stirring was continued for 24 hr. The mixture was partitioned between ethyl acetate and dilute HCl. The ethyl acetate layer was washed with water followed by brine and dried over Na2SO4. The extract was concentrated to dryness to leave the title product as a pale yellow friable foam, (2.0 g, 74%, >90% purity, estimated from NMR). 1H NMR (300 MHz, DMSO-D6) delta ppm 1.28-1.49 (m, 3 H) 1.59-2.04 (m, 7 H) 2.74-2.82 (m, 1 H) 2.88 (s, 6 H) 7.57 (dd, J=8.42, 1.46 Hz, 1 H) 7.74 (d, J=8.78 Hz, 1 H) 7.91 (s, 1 H) 11.71 (s, 1 H) 12.08 (s, 1 H).An alternative method for the preparation of 1H-indole-6-carboxamide, 2-bromo-3-cyclohexyl-N-[(dimethylamino)sulfonyl]- is described below.To a 1 L four necked round bottom flask equipped with a mechanical stirrer, a temperature controller, a N2 inlet, and a condenser, under N2, was added 2-bromo-3-cyclohexyl-1H-indole-6-carboxylic acid (102.0 g, 0.259 mol) and dry THF (300 mL). After stirring for 10 min, CDI (50.3 g, 0.31 mol) was added portion wise. The reaction mixture was then heated to 50 C. for 2 h. After cooling to 30 C., N,N-dimethylaminosulfonamide (41.7 g, 0.336 mol) was added in one portion followed by addition of DBU (54.1 mL, 0.362 mol) drop wise over a period of 1 h. The reaction mixture was then stirred at rt for 20 h. The solvent was removed in vacuo and the residue was partitioned between EtOAc and 1 N HCl (1:1, 2 L). The organic layer was separated and the aqueous layer was extracted with EtOAc (500 mL). The combined organic layers were washed with brine (1.5 L) and dried over MgSO4. The solution was filtered and concentrated in vacuo to give the crude product (111.0 g). The crude product was suspended in EtOAc (400 mL) at 60 C. To the suspension was added heptane (2 L) slowly. The resulting suspension was stirred and cooled to 0 C. It was then filtered. The filter cake was rinsed with small amount of heptane and house vacuum air dried for 2 days. The product was collected as a white solid (92.0 g, 83%). 1H NMR (MeOD, 300 MHz) delta 7.89 (s, H), 7.77 (d, J=8.4 Hz, 1H), 7.55 (dd, J=8.4 and 1.8 Hz, 1H), 3.01 (s, 6H), 2.73-2.95 (m, 1H), 1.81-2.05 (m, 8H), 1.39-1.50 (m, 2H); m/z 429 (M+H)+.

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 N,N-Dimethylsulfamide.

Reference:
Patent; Bristol-Myers Squibb Company; US2008/227769; (2008); A1;,
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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 2675-89-0 as follows. 2675-89-0

Prepared according to a procedure similar to that described for ethyldimethylphosphine borane I-23 starting from 2-chloro-N,N-dimethylacetamide (396 mg, 3.1 mmol) (except reaction performed at rt) to provide the title compound as a colourless oil (231 mg, 1.2 mmol, 84%).

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:
Patent; AUSPHERIX LIMITED; KING, Nigel Paul; POWELL, Jonathan Raymond; NEGOITA-GIRAS, Gabriel; WATTS, Joseph Michael; ALVAREZ, Alicia Galvan; GUETZOYAN, Lucie Juliette; FREEM, Joshua Robert; CLARKE, Philip Graham; NAYLOR, Alan; (264 pag.)WO2018/220171; (2018); A1;,
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Adding some certain compound to certain chemical reactions, such as: 1122-56-1, name is Cyclohexanecarboxamide, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 1122-56-1. 1122-56-1

General procedure: The benzamide (0.2 mmol), NaH (3 equivalents) and dry THF(3 mL) were added to a two-neck flask in turn and stirred atroom temperature for 1 h. Then disulfide (1.5 equivalent) wasadded into the mixture and stirred for another 36 h at roomtemperature. During the whole reaction process, the systemwas kept turbid because of the difficult solubility of NaH inTHF. Then the resulting mixture was filtered and washed withEtOAc to give the solvent, which was concentrated in vacuoand the residue was purified by flash column chromatographyon a silica gel to give the desired product

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 Cyclohexanecarboxamide.

Reference:
Article; Zhang, Xing-Song; Zhang, Xiao-Hong; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 191; 1; (2016); p. 89 – 94;,
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16066-84-5, 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 16066-84-5 as follows.

To a solution of tert-butyl N-methylcarbamate (300 mg, 2.29 mmol, CAS16066-84-5) in DMF (10 mL) was added NaH (183 mg, 4.58 mmol, 60% purity) at 0 C. The mixture was stirred at 25 C. for 2 hours. Then non-8-ynyl methanesulfonate (0.5 g, 2.29 mmol, synthesized via Step 1 of Intermediate GQ) in dry DMF (2 mL) was added at 0 C., and then the mixture was stirred at 25 C. for 5 hours. On completion, the mixture was quenched by addtion H2O (30 mL), then extracted with EA (3¡Á50 mL), and the organic phase was concentrated in vacuo to give a residue. The residue was purified by flash silica gel chromatography to give the title compound (410 mg, 70% yield) as colorless oil. 1H NMR (400 MHz, DMSO-d6) delta 3.14 (t, J=7.6 Hz, 2H), 2.75 (s, 3H), 2.74-2.72 (m, 1H), 2.17-2.11 (m, 2H), 1.48-1.42 (m, 4H), 1.39 (s, 9H), 1.35-1.18 (m, 6H).

According to the analysis of related databases, tert-Butyl methylcarbamate, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Kymera Therapeutics, Inc.; Mainolfi, Nello; Ji, Nan; Kluge, Arthur F.; Weiss, Matthew M.; Zhang, Yi; (1443 pag.)US2019/192668; (2019); 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. 107017-73-2, name is tert-Butyl (1-(hydroxymethyl)cyclopropyl)carbamate, A new synthetic method of this compound is introduced below., 107017-73-2

To a solution of tert-butyl (1-(hydroxymethyl)cyclopropyl)carbamate (3.5 g; 18.7 mmol) and imidazole (2.54 g; 37.4 mmol) in DCM (40 mL) was added TBDPSC1 (4.11 mL;18.7 mmol). The reaction mixture was stirred for 4 h. Water (50 mL) and DCM (20 mL) were added. The two layers were separated and the aq. phase was extracted twice with DCM (2 x 25 mL). The evaporation residue was purified by CC (EA-Hept) to afford the title compound (8.85 g; >95% yield) as a colorless oil.?H NMR (d6-DMSO) oe: 7.64-7.60 (m, 4H); 7.49-7.40 (m, 6H); 7.20 (s, 1H); 3.66 (s, 2H);1.36 (br s, 9H); 1.00 (s, 9H); 0.7 1-0.65 (m, 2H); 0.64-0.60 (m, 2H).MS (ESI, mlz): 426.1 [M+Hj for C25H35NO3Si; tR = 1.11 mm.

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; ACTELION PHARMACEUTICALS LTD; PANCHAUD, Philippe; SCHMITT, Christine; SURIVET, Jean-Philippe; (141 pag.)WO2017/36968; (2017); A1;,
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107017-73-2, A common heterocyclic compound, 107017-73-2, name is tert-Butyl (1-(hydroxymethyl)cyclopropyl)carbamate, molecular formula is C9H17NO3, 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.

To a solution of tert-butyl (1-(hydroxymethyl)cyclopropyl)carbamate (3.5 g; 18.7 mmol)and imidazole (2.54 g; 37.4 mmol) in DCM (40 mL) was added TBDPSCl (4.11 mL;18.7 mmol). The reaction mixture was stirred for 4 h. Water (50 mL) and DCM (20 mL)were added. The two layers were separated and the aq. phase was extracted twice with25 DCM (2 x 25 mL).The evaporation residue was purified by CC (EA-Hept) to afford thetitle compound as a colourless oil (8.85 g; > 95% yield).1H NMR (d6-DMSO) o: 7.64-7.60 (m, 4H); 7.49-7.40 (m, 6H); 7.20 (s, 1H); 3.66 (s, 2H);1.36 (br. s, 9H); 1.00 (s, 9H); 0.71-0.65 (m, 2H); 0.64-0.60 (m, 2H).MS (ESI, m/z): 426.1 [M+H+] for CzsH3sN03Si; tR = 1.11 min.

The synthetic route of tert-Butyl (1-(hydroxymethyl)cyclopropyl)carbamate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; IDORSIA PHARMACEUTICALS LTD; DIETHELM, Stefan; MIRRE, Azely; PANCHAUD, Philippe; SCHMITT, Christine; SURIVET, Jean-Philippe; (99 pag.)WO2017/198647; (2017); A1;,
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Adding a certain compound to certain chemical reactions, such as: 20348-09-8, name is 2H-Pyrido[3,2-b][1,4]oxazin-3(4H)-one, belongs to amides-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 20348-09-8, 20348-09-8

PREPARATION B; Phenyl 3-[(diphenoxyphosphoryl)oxy]-2,3-dihydro-4H-pyrido-[3,2-b][1,4]oxazine-4-carboxylate; Step A: Phenyl 2,3-dihydro-4H-pyrido[3,2-b][1,4]oxazin-3-one-4-carboxylate; Under an anhydrous atmosphere, a solution of 10 mmol of 2H-pyrido[3,2-b][1,4]oxazin-3-one in 50 ml of tetrahydrofuran is cooled to -78 C. At that temperature, 11 mmol of a 1.6M solution of n-butyllithium in hexane are added dropwise. After 30 minutes’ contact at -78 C., 11 mmol of phenyl chloroformate are added dropwise and stirring is maintained for a further 2 hours. After returning to ambient temperature, the solution is hydrolysed and then extracted with ethyl acetate. The organic phase is dried over magnesium sulphate, filtered and evaporated. After purification by chromatography on silica gel (petroleum ether/ethyl acetate: 8/2), the expected product is isolated. Melting point: 97 C. IR (KBr): vC=O=1717 cm-1; 1803 cm-1. Mass spectrum: m/z 271 (M+1).

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, 2H-Pyrido[3,2-b][1,4]oxazin-3(4H)-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Coudert, Gerard; Lepifre, Franck; Caignard, Daniel-Henri; Renard, Pierre; Hickman, John; Pierre, Alain; Kraus-Berthier, Laurence; US2006/3997; (2006); A1;,
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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. 402-46-0, name is 4-Fluorobenzenesulfonamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 402-46-0

EDCI (111 mg, 0.5 mmol) was added to a solution of (R)-5-(2-(2,5-difluorophenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyridine-3-carboxylic acid (100 mg, 0.29 mmol) in DCM (4 mL) followed by DMAP (36 mg, 0.29 mmol) and 4-fluorobenzenesulfonamide (56 mg, 0.31 mmol) and stirring was continued at 20-35 C. for 20 h. Reaction mixture was quenched with water, extracted into EtOAc, dried over anhydrous sodium sulphate and concentrated under reduced pressure to afford the crude. The crude compound was purified by Preparative HPLC [Column: 21.2*150*5 um, Zorbax, Eclipse, C-18, Mobile phase-A: Water, B:ACN, Gradient (Time/% B): 0/30, 2/40, 10/80 and Flow rate: 20 mL/min] to afford 9.3 mg of the title compound. 1H NMR (400 MHz, CDCl3) delta ppm 8.29 (1H, bs), 8.22-8.20 (2H, m), 8.12 (1H, d, J=7.6 Hz), 8.00 (1H, s), 7.26-7.20 (2H, m), 7.14-7.04 (2H, m), 6.96-6.88 (1H, m), 6.61 (1H, m), 6.18 (1H, d, J=7.6 Hz), 5.12-5.11 (1H, d, J=8 Hz), 3.80-3.74 (1H, m), 3.6-3.5 (1H, m), 2.5-2.4 (1H, m), 2.15-2.0 (3H, m). MS (ESI): m/z 501.8 (M+H).

The synthetic route of 402-46-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DR. REDDY’S LABORATORIES LTD.; Sasmal, Pradip Kumar; Ahmed, Shahadat; Tehim, Ashok; Pradkar, Vidyadhar; Dattatreya, Prasanna M.; Mavinahalli, Nanjegowda Jagadeesh; US2014/371217; (2014); A1;,
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These common heterocyclic compound, 17193-28-1, name is 1-Amino-1-cyclopentanecarboxamide, 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. 17193-28-1

General procedure: 1-amino-cyclopentanecarboxamide (3) (8.0 g, 62.5 mmol) was acylated with alkyl acyl chloride (93.7 mmol) and triethylamine (17.3 mL, 125.0 mmol) in 50 mL dichloromethane(DCM) at 0 C.After the reaction was completed, the resulting mixture was addedwith 30 mLwater, and extracted with DCM (25 mL 3). The organiclayer was dried over MgSO4. After filtration, the solvent wasremoved under reduced pressure. The residue was dissolved in50 mL MeOH and then 50 mL 10 M KOH was added slowly. Themixturewas refluxed for 3 h. After cooled to room temperature, themixture was added 50 mL H2O and extracted with DCM(30 mL 4). The organic layer was dried over MgSO4, the solventwas removed under reduced pressure. The resulting residue waspurified by CC to give 5a-d.

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 17193-28-1.

Reference:
Article; Bao, Xiaolu; Zhu, Weibo; Yuan, Weidong; Zhu, Xingbo; Yan, Yijia; Tang, Hesheng; Chen, Zhilong; European Journal of Medicinal Chemistry; vol. 123; (2016); p. 115 – 127;,
Amide – Wikipedia,
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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.

To a solution of isopropyl carbamate (15.85 g, 154 mmol) in anhydrous THF (150 mL) in a flame-dried flask at -78 C was added crotonoyl chloride (14.16 mL, 146 mmol), followed by LiHMDS (300 mL, 1.0 M in THF). After 30 minutes of stirring at -78 C, solution was permitted to warm to RT and stir at RT overnight. Reaction was quenched via addition of sat. aq. NH4Cl (200 mL). Solution was extracted with EtOAc (3 x 75 mL). (0759) Combined organics were washed with sat NaCl and dried with MgSO4, filtered and concentrated under reduced pressure. Crude product was purified via automated normal phase chromatography (23% EtOAc in hexanes) to provide the desired imide as a white solid (12.3 g, 64% yield). mp 91 C. LCMS/UPLC (method: formate) retention time 0.82 min, [M + H]+ = 172.27.1H NMR (400 MHz, CDCl3) delta 7.55 (s, 1H), 7.14 (dq, J = 15.3, 6.9 Hz, 1H), 6.86 (dq, J = 15.2, 1.7 Hz, 1H), 4.99 (p, J = 6.3 Hz, 1H), 1.94 (dd, J = 6.9, 1.7 Hz, 3H), 1.30 (d, J = 6.3 Hz, 6H).13C NMR (126 MHz, CDCl3) delta 166.03, 151.36, 146.34, 122.94, 70.23, 21.78, 18.40.

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; ST. JUDE CHILDREN’S RESEARCH HOSPITAL; GUY, R., Kip; SLAVISH, P., Jake; SHADRICK, William, Robert; YOUNG, Brandon, M.; BOYD, Vincent, A.; BHARATHAM, Nagakumar; PRICE, Jeanine, E.; SHELAT, Anang; (324 pag.)WO2018/111805; (2018); A1;,
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