Category: 2851-13-0

Some common heterocyclic compound, 2851-13-0, name is N,N-Dimethyl-1H-benzo[d]imidazol-2-amine, molecular formula is C9H11N3, 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. Recommanded Product: 2851-13-0

Scheme 3 exemplifies a method of forming compounds of Formula I. Chloro purines (4) (1 mmol) can be coupled with R3-H (for example, wherein R3 is benzimidazol-1-yl) (1.03-1.30 mmol), under Buchwald conditions, for example tris(dibenzylideneacetone)-dipalladium(0) (0.02-0.05 mmol), XPhos (0.10-0.20 mmol), cesium carbonate (2 mmol) in DMF (7-10 mL) with heating under microwave at 140-150 C. for 30 minutes to form purines of Formula I. Formula I purines can be further purified by diluting with EtOAc, filtering the contents of the reaction, concentrating and purifying with flash chromatography or reverse phase HPLC. Formula I purines can be further derivatized in subsequent transformations to functionalize R1, for example by deprotecting any protected functional groups (for example deprotecting BOC-protected amine groups followed by additional steps, such as reductive amination, amide coupling or acylation to form additional compounds of Formula I.Example 131 1-(3-(2-(2-(dimethylamino)-1H-benzo[d]imidazol-1-yl)-9-methyl-6-morpholino-9H-purin-8-yloxy)azetidin-1-yl)-2-methylpropan-1-one 131 The compound was prepared from 1-(3-(2-chloro-9-methyl-6-morpholino-9H-purin-8-yloxy)azetidin-1-yl)-2-methylpropan-1-one and N,N-dimethyl-1H-benzo[d]imidazol-2-amine following General Procedure of Buchwald coupling shown in Scheme 3. 1H NMR (400 MHz, CDCl3) delta 8.29 (s, OH), 7.58 (d, J=7.5 Hz, 1H), 7.49 (d, J=7.8 Hz, 1H), 7.15 (dd, J=11.0, 4.3 Hz, 1H), 7.01 (dd, J=10.1, 4.2 Hz, 1H), 5.58-5.45 (m, 1H), 4.60 (d, J=7.2 Hz, 2H), 4.53-4.39 (m, 2H), 4.31 (d, J=9.6 Hz, 1H), 4.19 (s, 5H), 3.88-3.74 (m, 4H), 3.65 (s, 2H), 3.60 (s, 1H), 3.17 (s, 1H), 2.98 (s, 4H), 2.56-2.42 (m, 1H), 1.14 (d, J=6.8 Hz, 5H). LCMS: M+H+=520.2.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2851-13-0, its application will become more common.

Reference:
Patent; Li, Jun; Safina, Brian; Sutherlin, Daniel P.; Sweeney, Zachary; US2012/15931; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 2851-13-0, name is N,N-Dimethyl-1H-benzo[d]imidazol-2-amine, belongs to imidazoles-derivatives 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 2851-13-0, category: imidazoles-derivatives

2-Acetylpyridine (1.12 cm3, 9.9 mmol) was added consecutively by syringe, to a solution of 2-(1-methylhydrazinyl)-1Hbenzo[d]imidazole (1.62 g, 9.9 mmol) in ethanol. The mixture was stirred and heated at 60 C for 48 h. The product was isolated by evaporation of the solvent and recrystallization of the residue from a minimum volume of CH3CN by the gradual addition of diethyl ether. Yield: 83% (2.19 g). ESI-MS: m/z (%) = 266 (100) [L+H]+, 288(30) [L+Na]+. 1H NMR (300 MHz, CD3CN): 8.21 (d, J = 4.5 Hz, 1H),7.73 (d, J = 8.0 Hz, 1H), 7.57 (t, J = 7.8 Hz, 1H), 7.06-7.23 (m, 5H),3.48 (s, 3H, CH3-N), 3.48 (s, 3H, CH3-CN) ppm. 13C NMR (CD3CN,100 MHz): 162.04, 157.09, 155.16, 148.93, 148.72, 136.81, 136.29,127.07, 124.41, 121.62, 77.31, 76.99, 76.54, 40.26, 16.38 ppm. IR (KBr): m(C-H)ar 3075m, 3058s, 3029s, m(CC) 1580m, 1564m,1517w, 1456s; m(CN) 1442s, 1400m, 1346w, 1311s, q(C-H)1198s, 1170vs, 1143m, 1085s, 990s, 952s, 885vs; c(C-H) 837s,806m, 789s, 762m, 735m, 641s, 608s, 548m, 438s, 414s cm1. Anal.Calc. for C15H15N5 (265.32): C, 67.90; H, 5.70; N, 26.4. Found: C,67.82; H, 5.77; N, 26.32%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, N,N-Dimethyl-1H-benzo[d]imidazol-2-amine, and friends who are interested can also refer to it.

Reference:
Article; Marcinkowski, Damian; Wa??sa-Chorab, Monika; Bocian, Aleksandra; Miko?ajczyk, Joanna; Kubicki, Maciej; Hnatejko, Zbigniew; Patroniak, Violetta; Polyhedron; vol. 123; (2017); p. 243 – 251;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem