Category: 150349-36-3

150349-36-3, name is 3-(N-Boc-N-methylamino)propylamine, 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. Computed Properties of C9H20N2O2

A mixture of methyl 2-benzyl-4-chloro-9H-pyrimido[4,5-b]indole-7-carboxylate (0.100 g, 0.284 mmol), Et3N (0.079 mL, 0.569 mmol) and tert-butyl (3-aminopropyl)(methyl)carbamate (0.080 g, 0.426 mmol) in MeOH (1 mL) was heated in a microwave oven at 140C for 40 minutes. The solvent was removed under reduced pressure and the residue was purified by flash chromatography to give 0.092mg of crude Boc derivative which was used directly in the next step. TFA (1.0 ml, 12.98 mmol) was added dropwise to a cold suspension of methyl 2-benzyl -((3-((tert- butoxycarbonyl)(methyl)amino)propyl)amino)-9H-pyrimido[4,5-b]indole-7-carboxylate (0.092 g, 0.183 mmol) and the mixture was allowed to warm to room temperature over 30 minutes. After dilution with toluene, the solvent was removed under reduced pressure and then the residue was diluted with EtOAc to produce 85mg of a solid used directly in the next step: HRMS m/z 404.2091 (M+H)+.

The synthetic route of 150349-36-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UNIVERSITE DE MONTREAL; SAUVAGEAU, Guy; GAREAU, Yves; RUEL, Rejean; GINGRAS, Stephane; FARES, Iman; WO2013/110198; (2013); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 150349-36-3, name is 3-(N-Boc-N-methylamino)propylamine, 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 150349-36-3, Application In Synthesis of 3-(N-Boc-N-methylamino)propylamine

To a dichloromethane solution of 1 ,1 -dimethylethyl (3- aminopropyl)methylcarbamate (1.07 g, 5.67 mmol) was added Lambda/-(1 -benzothien-2- ylcarbonyl)-L-leucine (1.50 g, 5.15 mmol), 3,4-dihydro-3-hydroxy-4-oxo-1 ,2,3- benzotriazine (HOOBT) (21 mg, 0.13 mmol), and N-methylmorpholine (NMM) (0.91 ml, 8.25 mmol). The mixture was stirred several minutes whereupon EDCHCI (1.09 g, 5.67 mmol) was added. The reaction mixture was stirred overnight at RT. The solution was washed with 10% citric acid and brine, dried (MgSO4), filtered and concentrated to a solid. Purification by silica gel column chromatography (30%-70% ethyl acetate/hexane) gave the product as a white solid in 85% yield (1.9g): MS (m/z): 362 (M+H)

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-(N-Boc-N-methylamino)propylamine, and friends who are interested can also refer to it.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2006/29210; (2006); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 150349-36-3, name is 3-(N-Boc-N-methylamino)propylamine, 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 150349-36-3, Safety of 3-(N-Boc-N-methylamino)propylamine

To a dichloromethane solution of 1 ,1 -dimethylethyl (3- aminopropyl)methylcarbamate (1.07 g, 5.67 mmol) was added Lambda/-(1 -benzothien-2- ylcarbonyl)-L-leucine (1.50 g, 5.15 mmol), 3,4-dihydro-3-hydroxy-4-oxo-1 ,2,3- benzotriazine (HOOBT) (21 mg, 0.13 mmol), and N-methylmorpholine (NMM) (0.91 ml, 8.25 mmol). The mixture was stirred several minutes whereupon EDCHCI (1.09 g, 5.67 mmol) was added. The reaction mixture was stirred overnight at RT. The solution was washed with 10% citric acid and brine, dried (MgSO4), filtered and concentrated to a solid. Purification by silica gel column chromatography (30%-70% ethyl acetate/hexane) gave the product as a white solid in 85% yield (1.9g): MS (m/z): 362 (M+H)

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-(N-Boc-N-methylamino)propylamine, and friends who are interested can also refer to it.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2006/29210; (2006); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 150349-36-3, name is 3-(N-Boc-N-methylamino)propylamine, 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 150349-36-3, HPLC of Formula: C9H20N2O2

Example A42; a) Preparation of intermediate 149; Pd/C 10% (4 g) was suspended in MeOH (200 ml) under N2 atmosphere. A 4% thiophene solution (4 ml) was added. The mixture was stirred at 25 0C under H2 atmosphere for pre-hydrogenation. First iV-(3-aminopropyl)-N-methylcarbamic acid 1,1-dimethylethyl ester (0.106 mol) and then benzaldehyde (0.106 mol) was added. The reaction mixture was stirred and hydrogenated at 25 0C under H2 atmosphere. After uptake of H2 (1 equiv), formaldehyde (0.106 mol) was added and the reaction mixture was hydrogenated further. After uptake of H2 (1 equiv), the catalyst was filtered off over dicalite and the filtrate was evaporated. The residue was purified over silica gel (eluent: DCM/CH3OH 95/5). The product fractions were collected and the solvent was evaporated to give an oil, yielding 26.5 g (71.7%) of intermediate 149.

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; JANSSEN PHARMACEUTICA NV; WO2009/16132; (2009); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 150349-36-3,Some common heterocyclic compound, 150349-36-3, name is 3-(N-Boc-N-methylamino)propylamine, molecular formula is C9H20N2O2, 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.

l,2-Dichloro-3-nitro-benzene (1.0 g, 5.2 mmol), (3-Amino-propyl)-methyl-carbamic acid tert- butyl ester (2.25 g, 11.9 mmol) and diisopropylethylamine (1.8 mL, 10.4 mmol) were combined and heated to about 100 0C. After about 3 days the reaction mixture was diluted with diethyl ether (200 mL) and IN HCl (200 mL). The organic layer was separated, washed with brine, dried (Na2SO4), filtered and concentrated in vacuo to provide 1.8 g of [3-(2-Chloro-6-nitro- pheny]amino)-propyl]-methyl-carbamic acid tert-butyl ester as an oil which was used in subsequent reactions without further purification. RP-HPLC R1 7.51 min. (table 1, method a); m/z: (M + H)+ 244.0. Preparation #9 [3-(2-chloro-6-nitro-phenylamino)-propyl]-methyl-carbamic acid tert-butyl ester l,2-Dichloro-3-nitro-benzene (1.0 g, 5.2 mmol), (3 -Amino-propyl )-methyl-carbamic ac id tert-butyl ester (2.25 g, 11.9 mmol) and diisopropylethylami?e (1.8 mL, 10.4 mmol) were combined and heated to about 100 0C. After about 3 days the reaction mixture was diluted with diethyl ether (200 mL) and IN HCl (200 mL). The organic layer was separated, washed with brine, dried (JSIa2SO4), filtered and concentrated in vacuo to provide 1.8 g of [3-(2-Chloro-6-nitro- phenylamino)-propyl]-methyl-carbamic acid tert-butyl ester as an oil which was used in subsequent reactions without further purification. RP-HPLC R1 7.51 min. (table 1, method a); m/z: (M + H)+ 244.0- To a solution of the above nitro aniline in acetic acid (53 mL) at room temperature was added iron powder (1.2 g, 21.2 mmol). After stirring for about 15 hours the reaction mixture was filtered and concentrated in vacuo. The crude product was dissolved in diethyl ether and washed with a solution of 2N NaOH that had been saturated with EDTA. The organic layer was further washed with brine, dried with Na2SO4, filtered and concentrated in vacuo to provide [3-(2-Amino-6-chloro-rhohenylamino)-propyl]-methyl-carbamic acid tert-butyl ester as a brown oil that was used in subsequent reactions without further purification. RP-HPLC R, 6.05 min. (table 1, method a). To a solution of the crude phenylene diamine in EtOH (98 mL) was added NaOAc (1.8 g, 22 mmol) followed by a 5 N solution of cyanogen bromide in acetonile (1.4 mL, 7.2 mmol). After stirring for about 20 hours at room temperature the reaction mixture was concentrated in vacuo. The crude reaction mixture was diluted with Et2O (200 mL) and 2 N NaOH (200 mL). The organic layer was separated, washed with brine, dried (Na2SO4), filtered and concentrated. The crude product was purified by column chromatography on silica gel (gradient elution 5-10% MeOH/CH2Cl2, containing 1% Et3N) to provide 1.3 g of [3-(7-Chloro-2- imino-2,3-dihydro-ben2oimJdazol-l-yl)-propyl]-methyl-carbamic acid tert-butyl ester as a brown oil. RP-HPLC R, 6.05 min (table 1, method a), m/z: (M+H)+ 339.0, 341.1 (3:1).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-(N-Boc-N-methylamino)propylamine, its application will become more common.

Reference:
Patent; ABBOTT LABORATORIES; WO2007/84728; (2007); A2;,
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. 150349-36-3, name is 3-(N-Boc-N-methylamino)propylamine, A new synthetic method of this compound is introduced below., HPLC of Formula: C9H20N2O2

Combined 6-(4-(4-cyanophenyl)-5-hydroxy-lH-pyrazol-l-yl)nicotinic acid (200 mg, 0.65 mmol) HATU (372 mg, 0.98 mmol), and Et3N (198 mg, 1.96 mmol) in DMF (3.0 mL) . The mixture was stirred at room temperature for 0.5 hour, then tert-butyl (3- aminopropyl)(methyl)carbamate (147.39 mg, 0.79 mmol) was added. The mixture was stirred overnight at room temperature. The reaction mixture was purified by preparative HPLC to give tert-butyl (3-(6-(4-(4-cyanophenyl)-5-hydroxy-lH-pyrazol-l- yl)nicotinamido)propyl)(methyl)carbamate (150 mg, 48%).

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; TAKEDA PHARMACEUTICAL COMPANY LIMITED; BROWN, Jason, W.; DAVIS, Melinda; IVETAC, Anthony; JONES, Benjamin; KIRYANOV, Andre, A.; KUEHLER, Jon; LANIER, Marion; MIURA, Joanne; MURPHY, Sean; WANG, Xiaolun; WO2014/160810; (2014); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 150349-36-3,Some common heterocyclic compound, 150349-36-3, name is 3-(N-Boc-N-methylamino)propylamine, molecular formula is C9H20N2O2, 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.

Ethyl theophylline-7-acetate 2 (266mg, 1 mmol) was suspended in ethanol (1 mL) in a conical vial and N-methyl-N-Bocpropane-1,3-diamine (330 mg, 1.75 mmol) was added. The vial was sealed and heated up to 110OC for 2 h. After purification by column chromatography (DCM/MeOH/Et3N95:5:1 ? 80:20:1), Boc group was removed by stirring intermediate 3b in 4M HCl(5mL). Aliquote of crude reaction mixture (1/3 rd) was neutralized with concentrated NaHCO3 and inorganic salts were precipitated by addition of ethanol (100 mL). After filtration, the solvents were removed in vacuo and the residue was recrystallized from ethyl acetate (hot solution was filtered to eliminate residual traces of inorganic salts). Monomethylated compound 4 was obtained as white solid in 20% unoptimized yield (60mg, 0.2 mmol)

The synthetic route of 150349-36-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Gibon, Julien; Kang, Min Su; Aliaga, Arturo; Sharif, Behrang; Rosa-Neto, Pedro; Seguela, Philippe; Barker, Philip A.; Kostikov, Alexey; Bioorganic and Medicinal Chemistry; vol. 24; 19; (2016); p. 4759 – 4765;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding some certain compound to certain chemical reactions, such as: 150349-36-3, name is 3-(N-Boc-N-methylamino)propylamine, 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 150349-36-3. 150349-36-3

24? was synthesized on 2-chlorotrityl resin using standard Fmoc chemistry by loading 1.1 mmol Fmoc glycine on resin, and subsequent coupling of Fmoc leucine, Fmoc phenylalanine, Fmoc glycine, and 6-maleimidohexanoic acid. Resin cleavage by addition of TFA, and trituration with MTBE, provided crude 24?. This was dissolved in DMF (5 mL), and N,N?-diisopropylcarbodiimide (277 mg, 2.20 mmol), HOBt (297 mg, 2.20 mmol) and diisopropylethylamine (0.5 mL) were added. The reaction was stirred at room temperature for 3 h, and purification by preparative HPLC (water with 0.05% TFA/acetonitrile) provided 25? (249 mg, 0.329 mmol, 30% yield). LCMS M/Z = 756.4 [M + 1].

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 3-(N-Boc-N-methylamino)propylamine.

Reference:
Patent; TARVEDA THERAPEUTICS, INC.; BILODEAU, Mark T.; SIMCOX, Mary; WHITE, Brian H.; KADIYALA, Sudhakar; WOOSTER, Richard; (178 pag.)WO2017/180834; (2017); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics