Category: 108468-00-4

A common heterocyclic compound, 108468-00-4, name is 1-(N-Boc-aminomethyl)-4-(aminomethyl)benzene, molecular formula is C13H20N2O2, 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. 108468-00-4.

General procedure: A solution of 4-(Boc-aminomethyl)benzylamine (3) (1.0 mmol) and TEA (3.0 mmol) in anhydrous DCM (8 mL) was cooled with an ice bath, then the corresponding sulfochloride (1.1 mmol, dissolved in 2 mL anhydrous DCM) was added dropwise. The reaction mixture was allowed to stir at 0 C for 1 h. After removing the cooling bath, the resulting mixture was stirred for 5 h at room temperature, then diluted with saturated aqueous NaHCO3 and extracted with DCM (10 mL) for three times. The combined organic layer was sequentially washed with water and brine, dried with anhydrous Na2SO4, and concentrated in vacuo. The crude was purified by column chromatography with DCM/methanol (150:1, v/v) to give the product as a white solid.

The synthetic route of 1-(N-Boc-aminomethyl)-4-(aminomethyl)benzene has been constantly updated, and we look forward to future research findings.

Reference:
Article; Bai, Renren; Liang, Zhongxing; Yoon, Younghyoun; Salgado, Eric; Feng, Amber; Gurbani, Saumya; Shim, Hyunsuk; European Journal of Medicinal Chemistry; vol. 136; (2017); p. 360 – 371;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 108468-00-4, 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 108468-00-4 as follows.

100 mg (0.109 mmol) of compound 3d was dissolved in 4 ml of DMF and cooled to -15 C. After addition of 36 tl (0.327 mmol) of NMM and 15 tl (0.109 mmol) CKIBE, the solution was stirred for 15 mm, followed by addition of 40mg (0.169 mmol) ofBoc-p-diaminoxylene and 12 tl (0.109 mmol) of NMM. The mixture was stirred for one hour at 0 C. and overnight at RT. The solvent was removed in vacuo, the residue was mixed with 1 ml 90% TFA and stirred for 2 h at RT. After removing the solvent in vacuo, the residue was dissolved in 8 ml of 30% B and purified by prep. HPLC (start at 10% B). Fractions containing the product were combined, the solvent was removed in vacuo and the residue dissolved in 80% t-butanol/water and lyophilized.jOllO] Yield: 39

According to the analysis of related databases, 108468-00-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PHILIPPS-UNIVERSITAeT MARBURG; Steinmetzer, Torsten; Saupe, Sebastian; US2014/213781; (2014); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 108468-00-4, name is 1-(N-Boc-aminomethyl)-4-(aminomethyl)benzene, 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 108468-00-4, HPLC of Formula: C13H20N2O2

Step 1: l-(N-boc-aminomethyl)-4-(aminomethyl) benzene (3.80g, 16.1 mmol) wasdissolved in DCM (100 mL) and DIPEA (5.0 mL, 29 mmol), followed by FmocCl (5.Og, 19 mmol)were added. The reaction mixture was stirred at room temperature for 1 hour, after which aprecipitate appeared. Water (100 mL) was added and the precipitate filtered and dried to give [4- (tert-butoxycarbonylamino-methyl)-benzyl]-carbamic acid 9H-fluoren-9-ylmethyl ester (6.32g, 86%) as a white solid. AnalpH2_MeOH_4MIN: Rt: 3.52 mm, mlz 481.3 [M+H]

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; UNIVERSITY OF LEEDS; PHILIPPOU, Helen; FOSTER, Richard; FISHWICK, Colin; REVILL, Charlotte; YULE, Ian; TAYLOR, Roger; NAYLOR, Alan; FALLON, Philip, Spencer; CROSBY, Stuart; HOPKINS, Anna; GUETZOYAN, Lucie, Juliette; MACNAIR, Alistair, James; STEWART, Mark, Richard; WINFIELD, Natalie, Louise; (273 pag.)WO2019/186164; (2019); A1;,
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. 108468-00-4, name is 1-(N-Boc-aminomethyl)-4-(aminomethyl)benzene, A new synthetic method of this compound is introduced below., Recommanded Product: 108468-00-4

HOBT (1.45 g, 10.9 mmol) is added to a solution of {3-[3-(3-carboxymethoxyprop-1-ynyl)phenyl]prop-2-ynyloxy}acetic acid (A30, 0.40 g, 1.3 mmol) and 4-N-tert-butoxycarbonylaminomethylbenzylamine (1.2 g, 5.2 mmol) in absolute CH2Cl2 (20 ml) and Et3N (2.5 ml), and the mixture is stirred at RT for 45 min. EDC (2.1 g, 10.9 mmol) is then added, and the mixture is stirred at RT overnight. The reaction solution is diluted with CH2Cl2 (15 ml) and extracted (2¡Á) with semisaturated aqueous NH4Cl solution (25 ml), dried over MgSO4, filtered off and concentrated under reduced pressure. Further purification by chromatography [Tol/Ac (8:2)] over a silica gel column gives the title compound (1.1 g) as a colorless powder. TLC, silica gel, glass plates, [Tol/Ac (7:3)], Rf=0.51.MS: calc.: C42H50N4O8 (738.0), found: [MH+] 738.8, [MNH4+] 755.8; [MNa+] 761.2

The synthetic route of 108468-00-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Altana Pharma AG; US6960588; (2005); B1;,
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. 108468-00-4, name is 1-(N-Boc-aminomethyl)-4-(aminomethyl)benzene, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 1-(N-Boc-aminomethyl)-4-(aminomethyl)benzene

2,4-dichloro-3-nitroquinoline (150 mg, 0.617 mmol) was dispersed in anhydrous DCM (10 mL) and stirred at room temperature for 5 min before a solution of l-(N-Boc-aminomethyl)-4-(aminomethyl)benzene (146 mg, 0.617 mmol) in DCM (lOmL) with EbN (90pL) was added in dropwise. This mixture was then stirred at 20 C for 3 h, then added asolution of l-(N-Boc-aminomethyl)-4-(aminomethyl)benzene (90 mg) with EbN (90 uL) and was allowed to stir at 20 C for 24 h, where LCMS saw full conversion of the dichloro-nitro-quinoline. The reaction mixture was diluted with DCM to 25 mL and was washed with brine, which was extracted with 2x 50 mL DCM. The combined organic phases were dried with Na2S04, filtered, and concentrated before the crude product was purified by flash column chromatography on silica (hexane/ethyl acetate 3:2). Product containing fractions with single spot by TLC were pooled and concentrated to an orange oil that was further concentrated to an orange solid at 0.2 mbar. Yielded 246.9 mg (90%). Rf = 0.57 (hexane/ethyl acetate 1 : 1 (v/v)). UPLCMS of product (LC2, C’ is): Retention time = 4.58 min. Calculated mass of C22H23CIN4O4 = 442.14; Observed [M+Na:M+Na+2]? as m/z = 465.1/467.2 in a 3: 1 ratio. NMR (400 MHz, DMSO-d6) d 8.53 (d, J= 8.5 Hz, 1H), 8.48 (t, J= 6.3 Hz, 1H), 7.88- 7.81 (m, 2H), 7.67 (ddd, J= 8.4, 5.3, 2.9 Hz, 1H), 7.36 (t, J= 6.2 Hz, 1H), 7.21 (d, J= 8.3 Hz, 2H), 7.17 (d, J= 8.4 Hz, 2H), 4.41 (d, J= 6.1 Hz, 2H), 4.09 (d, J= 6.2 Hz, 2H), 1.38 (s, 9H).13C NMR (101 MHz, DMSO) d 155.8, 145.3, 144.4, 141.1, 139.5, 136.1, 132.3, 128.6, 127.0, 126.9, 126.7, 126.5, 123.1, 119.7, 77.8, 46.6, 43.0, 28.2.

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 108468-00-4.

Reference:
Patent; TORQUE THERAPEUTICS, INC.; ANDRESEN, Thomas Lars; HENRIKSEN, Jonas Rosager; KRAEMER, Martin Kisha; (217 pag.)WO2020/23680; (2020); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 108468-00-4, 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. 108468-00-4, name is 1-(N-Boc-aminomethyl)-4-(aminomethyl)benzene belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A. {(S)-l-[4-(tert-Butoxycarbonylamino-methyl)-benzylcarbamoyl]-2-phenyl-ethyl}- carbamic acid benzyl ester (S)-2-Benzyloxycarbonylamino-3-phenyl-propionic acid 2,5-dioxo-pyrrolidin-l-yl ester (4.25g, 10.72mmol) was dissolved in CH2CI2 (100 mL). This solution was cooled to 0C. l-(N-Boc- Aminomethyl)-4-(aminomethyl)benzene (2.79g, 11.79mmol) was added followed by triethylamine (3.25g, 32.16mmol). After 18 hrs at 0C to room temperature reaction mixture was diluted with chloroform (100 mL) and washed with NaHC03 (1×30 mL), water (1×30 mL), brine (1×30 mL), dried (Na2S04) evaporated in vacuo giving a yellow oil. The residue was triturated with Pet. Ether (60-80C) and EtOAc to give a white solid identified as {(S)-l-[4-(tert- butoxycarbonylamino-methyl)-benzylcarbamoyl]-2-phenyl-ethyl}-carbamic acid benzyl ester (3.88g, 7.49mmol, 70%). [M+H]+ = 518.28, 540.32 (M+Na).

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, 1-(N-Boc-aminomethyl)-4-(aminomethyl)benzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; KALVISTA PHARMACEUTICALS LIMITED; EVANS, David Michael; DAVIE, Rebecca Louise; EDWARDS, Hannah Joy; ROOKER, David Philip; WO2013/5045; (2013); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

A common heterocyclic compound, 108468-00-4, name is 1-(N-Boc-aminomethyl)-4-(aminomethyl)benzene, molecular formula is C13H20N2O2, 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. 108468-00-4.

General procedure: A solution of 4-(Boc-aminomethyl)benzylamine (3) (1.0 mmol) and TEA (3.0 mmol) in anhydrous DCM (8 mL) was cooled with an ice bath, then the corresponding sulfochloride (1.1 mmol, dissolved in 2 mL anhydrous DCM) was added dropwise. The reaction mixture was allowed to stir at 0 C for 1 h. After removing the cooling bath, the resulting mixture was stirred for 5 h at room temperature, then diluted with saturated aqueous NaHCO3 and extracted with DCM (10 mL) for three times. The combined organic layer was sequentially washed with water and brine, dried with anhydrous Na2SO4, and concentrated in vacuo. The crude was purified by column chromatography with DCM/methanol (150:1, v/v) to give the product as a white solid.

The synthetic route of 1-(N-Boc-aminomethyl)-4-(aminomethyl)benzene has been constantly updated, and we look forward to future research findings.

Reference:
Article; Bai, Renren; Liang, Zhongxing; Yoon, Younghyoun; Salgado, Eric; Feng, Amber; Gurbani, Saumya; Shim, Hyunsuk; European Journal of Medicinal Chemistry; vol. 136; (2017); p. 360 – 371;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

108468-00-4, Name is 1-(N-Boc-aminomethyl)-4-(aminomethyl)benzene, 108468-00-4, belongs to amides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows.

EXAMPLE 134 N-(4-tert.butoxycarbonylaminomethyl-phenylmethyl)-3-(4′-trifluoromethylbiphenyl-2-carbonylamino)-benzoic acid amide Prepared analogously to Example 34 from 3-(4′-trifluoromethyl-biphenyl-2-carbonylamino)-benzoic acid, 4-(tert.butoxycarbonyl-aminomethyl)-benzylamine, TBTU and N-ethyldiisopropylamine in dimethylformamide. Yield:89% of theory Rf value:0.70 (silica gel; dichloromethane/ethanol 9:1)

Statistics shows that 1-(N-Boc-aminomethyl)-4-(aminomethyl)benzene is playing an increasingly important role. we look forward to future research findings about 108468-00-4.

Reference:
Patent; Priepke, Henning; Hauel, Norbert; Thomas, Leo; Mark, Michael; Dahmann, Georg; US2002/32238; (2002); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

108468-00-4, 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. 108468-00-4, name is 1-(N-Boc-aminomethyl)-4-(aminomethyl)benzene, A new synthetic method of this compound is introduced below.

820 mg of tert-butyl N-[[4-(aminomethyl)-phenyl]-methyl]-carbamate and 421 mg of TEA was dissolved in 10 mL of DCM, cooled in an ice bath and 725 mg of thioacetic acid S-(4-chlorocarbonyl-phenyl) ester, dissolved in 5 mL of DCM, was slowly added. The mixture obtained was stirred for 30 min at rt, the phases were separated, the organic phase obtained was washed successively with 2N HCl and 5% aqueous NaHCO3 solution, dried over Na2SO4 and evaporated to dryness. The title compound was obtained in the form of pale brown crystals.

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; NABRIVA THERAPEUTICS AG; Thirring, Klaus; Heilmayer, Werner; Riedl, Rosemarie; Kollmann, Hermann; Ivezic-Schoenfeld, Zrinka; Wicha, Wolfgang; Paukner, Susanne; Strickmann, Dirk; (90 pag.)US2016/332963; (2016); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

A common heterocyclic compound, 108468-00-4, name is 1-(N-Boc-aminomethyl)-4-(aminomethyl)benzene, molecular formula is C13H20N2O2, 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. 108468-00-4.

Compound 3 (19.6 g, 83.1 mmol, 1 equiv; corresponding to 42.5 g of a mixture with di-Boc-protected 1,4-bis(aminomethyl)benzene, cf. preparation of 3) was suspended in water (500 mL) and ethanol (400 mL). The suspension was heated to 60 C and 1 M aq hydrochloric acid (100 mL) was added yielding a pH of about 3. Potassium cyanate (7 g, 86.3 mmol) was added and the mixture was refluxed for 75 min. 1 M aq hydrochloric acid (8 mL) was added to adjust the pH to 7, followed by the addition of 4.67 g potassium cyanate (4.67 g, 57.6 mmol). Reflux was continued for 2 h, then the mixture was stirred at rt overnight (final pH: ?8) and concentrated under reduced pressure to a volume of about 200 mL. The white solid was separated by filtration, washed twice with water (2 ¡Á 150 mL) and dried in vacuo. A suspension was prepared in a mixture of MeOH and DCM (1:10, 2000 mL) and subjected to column chromatography (DCM/MeOH 20:1-7.5:1). The isolated Boc-protected intermediate (well soluble in MeOH, poorly soluble in water, acetonitrile, ethyl acetate and DCM) was dissolved in MeOH (300 mL) under mild heating. Acetyl chloride (30 mL) was added dropwise over a period of 2 h and stirring was continued for 30 min. Volatiles were removed under reduced pressure and the residue was suspended in water (150 mL). Lyophilisation afforded the product as a white solid (15.8 g, 88%). 1H NMR (300 MHz, MeOH-d4/D2O 80:20): delta (ppm) 4.06 (s, 2H), 4.26 (s, 2H), 7.34 (m, 4H); MS (CI, NH3): m/z 197 [M+NH4]+, 180 [M+H]+; C14H21N3O3 ¡Á HCl (215.8).

The synthetic route of 1-(N-Boc-aminomethyl)-4-(aminomethyl)benzene has been constantly updated, and we look forward to future research findings.

Reference:
Article; Keller, Max; Erdmann, Daniela; Pop, Nathalie; Pluym, Nikola; Teng, Shangjun; Bernhardt, Guenther; Buschauer, Armin; Bioorganic and Medicinal Chemistry; vol. 19; 9; (2011); p. 2859 – 2878;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics