Tag: M.W=200-300

Synthetic Route of 201162-53-0,Some common heterocyclic compound, 201162-53-0, name is 3-Boc-3,8-Diazabicyclo[3.2.1]octane, 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.

To a solution of /er/-butyl 3,8-diazabicyclo[3.2. l]octane-3-carboxylate (1.0 equiv) and DIEA (2.0 equiv) in dry DCM at 0C was added BrCN (1.5 equiv). The mixture was stirred at 0C for lh and then at rt overnight. The reaction mixture was washed with water and brine to afford /c/7-butyl 8-cyano-3,8-diazabicyclo[3.2.l]octane-3-carboxylate which was used without further purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Boc-3,8-Diazabicyclo[3.2.1]octane, its application will become more common.

Reference:
Patent; ESCALIER BIOSCIENCES B.V.; MOHAN, Raju; NUSS, John; HARRIS, Jason; YUAN, Shendong; (144 pag.)WO2019/177996; (2019); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 53844-02-3, A common heterocyclic compound, 53844-02-3, name is Benzyl (2-bromoethyl)carbamate, molecular formula is C10H12BrNO2, 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 stirred solution of bromide (1 mmol) and 4-amino-1-butanol (0.36 g, 4 mmol, 4 eq.) in anhydrous DMF (10 ml) under N2, was added anhydrous K2CO3 (0.276 g, 2 mmol, 2 eq.) and sodium iodide (15 mg, 0.1 mmol, 0.1 eq.). The reaction was stirred for 72 hours at room temperature, until reaction complete. The DMF was evaporated in vacuo and dried exhaustively under high vacuum. The resulting oily solid was redissolved in CH2Cl2 (100 ml) and washed with water (4 x 50 ml). The combined aqueous extracts were then washed with CH2Cl2 (40 ml) and the CH2Cl2 extracts dried over anhydrous Na2SO4. The CH2Cl2 was evaporated in vacuo to give a pale yellow oil.

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; IC-VEC LIMITED; EP918790; (2004); B1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Related Products of 4793-24-2, These common heterocyclic compound, 4793-24-2, name is 2-Chloro-4-fluoro-5-sulfamoylbenzoic acid, 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.

Compound 1 was dissolved in 1 mL of compound 2 and heated to 10OC and monitored by TLC until complete. When complete, as indicated by TLC, the reaction was removed from the heat. A pale yellow goo remained, containing crystals. To this mixture was added IM HCl and this stirred for 10 min. At this time, a precipitate fell out of solution that was subsequently filtered to yield the pure product as indicated by NMR.IH NMR: 8.25 (s, IH), 7.5-7.2 (m, 5H), 6.71 (s, IH), 4.54 (s, 2H), 4.0 (s, IH), 3.3 (s, 2H).Ms API-ES Neg. Scan calculated for C14H12C1N2O4S- 339.02. ; obtained 339.2

The synthetic route of 4793-24-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FLYNN, Gary, A.; YOOL, Andrea, J.; MIGLIATI, Elton, Rodrigues; RITTER, Leslie, S.; WO2008/52190; (2008); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 6325-93-5,Some common heterocyclic compound, 6325-93-5, name is 4-Nitrobenzenesulfonamide, molecular formula is C6H6N2O4S, 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: The catalytic reduction of nitro aromatics was conducted in a 25 mlTelfon-lined stainless steel autoclave with magnetic stirring. In a typicalprocess, 6 mmol nitroarene, and desired amounts of reducing agent andsolvents were introduced in the reactor. The autoclave was transferredinto a water bath at the set temperature with an accuracy of better than0.2 C for ?0.5 h. Then, 10 mg catalyst was added into the reactionmixture and started the reduction at a stirring rate of 450 rpm. After thereaction, the catalyst was rapidly separated by ltration. n-Decane(500 muL) as standard was added into the ltrate and was dried withanhydrous Na 2 SO 4 . The products were analyzed by gas chromato-graphy-mass spectrometry (GC-MS) (Shimadzu GCMS-QP2010 Plus)and GC (Varian CP-3800) with a capillary column (column VF-1 ms,15 m, 0.25 mm, 0.25 mum) and a ame ionization detector (FID).

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

Reference:
Article; Huang, Haigen; Liang, Xiangcheng; Wang, Xueguang; Sheng, Yao; Chen, Chenju; Zou, Xiujing; Lu, Xionggang; Applied Catalysis A: General; vol. 559; (2018); p. 127 – 137;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Related Products of 40724-47-8,Some common heterocyclic compound, 40724-47-8, name is 4-Bromomethylbenzenesulfonamide, molecular formula is C7H8BrNO2S, 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.

4-Azidomethyl-benzenesulfonamide (INT-2); To a stirred solution of 4-bromomethyl-benzenesulfonamide (4.500 g,17.9917 mmol) (prepared from 4-bromomethyl-benzenesulfonyl chloride upon treatment with ammonia (as described by Yee YK et al. in Journal of Medicinal Chemistry 1990 33 (9) 2437-2451 ) in lambda/,lambda/-dimethylformamide (30 ml), sodium azide is added (1 1 .696 g, 179.917 mmol) and the reaction mixture is heated at 900C for 14 hours under a nitrogen atmosphere. The suspension is filtered, to remove the excess of sodium azide, and the solid residue is washed with ethyl acetate (4 x 50 ml). The mother liquids are concentrated, to afford a crude yellow liquid (3.820 g, 100% mass balance), that is used as such for the next step. IR: 2098.8 cm”1.

The synthetic route of 40724-47-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NEUROSEARCH A/S; WO2009/112459; (2009); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 703-12-8, 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. 703-12-8 name is 4-Bromo-N-methylbenzenesulfonamide, 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.

Step b: 4-(lambdar-Methylsulfamoyl)phenylboronic acid; To a solution of 4-bromo-iV-methyl-benzene sulfonamide (24.9 g, 0.1 mol) and B(O1Pr)3 (28.2 g, 0.15 mol) in THF (200 mL) was added n-BuLi (100 mL, 0.25 mol) at -70 0C. The mixture was slowly warmed to 0 0C, then 10% HCl solution was added until pH 3-4. The resulting mixture was extracted with EtOAc. The organic layer was dried over Na2SO4, and evaporated under reduced pressure to give 4-(iV-methylsulfamoyl)phenylboronic acid (22.5 g, 96%), which was used in the next step without further purification. 1H NMR (DMSO-J6, 300 MHz) delta 8.29 (s, 2 H), 7.92 (d, J = 8.1 Hz, 2 H), 7.69 (d, J = 8.4 Hz, 2 H), 2.36 (d, J = 5.1 Hz, 3 H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Bromo-N-methylbenzenesulfonamide, and friends who are interested can also refer to it.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; WO2007/56341; (2007); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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. 2618-96-4, name is Dibenzenesulfonimide, This compound has unique chemical properties. The synthetic route is as follows., category: amides-buliding-blocks

General procedure: To a solution of N-sulfonylsulfonamide 1 (1.68 mmol) in N,N-disubstituted formamide 3 (3.0 mL) was added TsCl (2; 0.160 g, 0.840 mmol; 0.480 g, 2.52 mmol for products 4d-g) and Et3N (0.29 mL, 2.10 mmol). The mixture was stirred at r.t. (or heated to 100 C in the cases of 4d-g,k). After the starting material was consumed as indicated by TLC, the reaction mixture was poured into H2O and extracted with CH2Cl2. The combined organic phases were washed with H2O, dried (anhydrous MgSO4), filtered, and concentrated under reduced pressure. The crude product was purified, if necessary, by silica gel flash column chromatography (hexane/EtOAc) to give the desired product as a white solid (Table 2).

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 2618-96-4.

Reference:
Article; Jeong, Yuri; Ban, Jaeyoung; Lim, Minkyung; Rhee, Hakjune; Synthesis; vol. 50; 9; (2018); p. 1867 – 1874;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 1259224-00-4, name is tert-Butyl (1-(4-aminophenyl)cyclobutyl)carbamate, 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 1259224-00-4, Safety of tert-Butyl (1-(4-aminophenyl)cyclobutyl)carbamate

To the solution of 2,4-Dichloro-6-methyl-5-nitro-pyrimidine (2.08 g, lO.OOmmol) in THF (50 mL) at -78 C was slowly added the solution of [l-(4-Amino-phenyl)- cyclobutyl]-carbamic acid tert-butyl ester (2.62 g, 10.00 mmol) in THF (20 mL). The reaction mixture was stirred at ambient temperature for 30 min.. Then it was concentrated to remove the solvent. The obtained residue was dissolved in ethyl acetate (250 mL) and washed by saturated. NaHC03 solution, followed by brine. The separated organic layer was dried over sodium sulfate, filtered and concentrated to give { l-[4-(2-Chloro-6-methyl-5-nitro-pyrimidin-4-ylamino)-phenyl]- cyclobutyl}-carbamic acid tert-butyl ester. (4.3 g, 98%yield). MS (ESI+) e/z: 370.9 / 372.9 [M+l]+.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; ARRAY BIOPHARMA INC.; GENENTECH, INC.; SKELTON, Nicholas; GRADL, Stefan; BLAKE, James F.; GRAHAM, James M.; GUNAWARDANA, Indrani W.; HENTEMANN, Martin; MARLOW, Allison L.; TANG, Tony P.; WO2013/78254; (2013); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 6325-93-5, name is 4-Nitrobenzenesulfonamide, 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 6325-93-5, COA of Formula: C6H6N2O4S

Step 1 – Tert-butyl N-(4-nitrophenyl)sulfonylcarbamate (0596) [00375] To a solution of 4-nitrobenzenesulfonamide (5.00 g, 24.7 mmol) in anhydrous dichloromethane (40 mL) was added triethylamine (5.00 g, 49.4 mmol) and catalytic amount of N,N-dimethylpyridin-4-amine. The mixture was cooled to 0 C and di-tert-butyl dicarbonate (5.67 g, 25.9 mmol) was added over 10 min. Then the mixture was warmed to 18 C and stirred for 50 min. On completion, the reaction mixture was quenched with ice water (40 mL). Afterwards, the organic phase was separated, washed with brine (20 mL), dried over anhydrous sodium sulfate and concentrated in vacuo to give a residue. The residue was purified by column chromatography (petroleum ether:ethyl acetate = 3:1 to 1:1) to give the title compound.1H NMR (400MHz, CDCl3) delta = 8.44 – 8.40 (m, 2H), 8.28 – 8.24 (m, 2H), 1.43 (s, 9H).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; RAZE THERAPEUTICS, INC.; MAINOLFI, Nello; MOYER, Mikel P.; SAIAH, Eddine; (264 pag.)WO2017/156181; (2017); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 112101-81-2,Some common heterocyclic compound, 112101-81-2, name is R-5-(2-Aminopropyl)-2-methoxybenzenesulfonamide, molecular formula is C10H16N2O3S, 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.

Into a 4-necked 500ml round bottom flask, equipped with Dean-stark apparatus 150.0ml of toluene, 24.4gms of (R)-5-(2-aminopropyl)-2-methoxy benzene sulfonamide of the formula-IV and 12.4gms (0.1mole) of 4-fluorobenzaldehyde are charged. The reaction is effected azeotropically and the water 1.8ml (0.1mole) is separated. Then the toluene is distilled off completely under vacuum at temp max 80C. Cooled 25-35C and released the vacuum under nitrogen atmosphere – 25.0gm of thick oily compound of 2-methoxy-5-(2R)-2-{[(1-E/Z-4-fluorophenylpmethylene)amino] propyl} benzenesulfonamide of formula-IIId is obtained. Recrystallized sample (from IPA) has the following characteristics MR : 140-148C 1H NMR : (200MHz, CDCl3+DMSO-d6) delta 1.01-1.04 (d, 3H), 2.80-2.88 (t, 2H), 3.14 – 3.18 (m, 1H), 3.88 (s, 3H), 6.0, (broad, 2H), 7.12-7.57 (aromatic, 7H), 8.20 (s, imine, 1H) IR : (KBr), 3385, 3315, 2948, 1643, 1606, 1576, 1495, 1404, 1334, 1249, 1154, 1074, 1114, 518, 471cm-1

The synthetic route of 112101-81-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NATCO PHARMA LIMITED; WO2004/16582; (2004); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics