Electric Literature of 29043-48-9, These common heterocyclic compound, 29043-48-9, name is 2-Methyl-1H-benzoimidazol-5-ylamine, 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.
The coupling reaction of 3-chloro-2-methylbenzenesulphonyl chloride (2 eq. ) with 2- methylbenzimidazoel (1 eq. ) under the condition described above yielded a mixture of 3- CHLORO-N- [1- (3-CHLORO-2-METHYLBENZENESULPHONYL)-2-METHYL-1 H-BENZOIMIDAZOL-5-YL]-2- methyl-benzenesulphonamide and 3-chloro-N-[1-(3-chloro-2-methylbenzenesulphonyl)- 2-METHYL-1 H-BENZOIMIDAZOL-6-YL]-2-METHYL-BENZENESULPHONAMIDE in 1: 1 ratio as judged by HNMR.’H NMR (270 MHz, DMSO): 5 10.7 (2H, s, 2 x NH), 7.86-7. 96 (3H, m, ArH), 7.65-7. 78 (5H, m, ArH), 7.52-7. 58 (5H, m, ArH), 7.25-7. 40 (3H, m, ArH), 7.07 (2H, t, J = 8.2 Hz, ArH), 2.61 (3H, s, CH3), 2.58 (3H, s, CH3), 2.54 (6H, s, 2 x CH3), 2.39 (3H, S, CH3), 2.33 (3H, s, CH3). The mixture (200 mg) was dissolved in THF (15 mL), N- hydroxybenzotriazole (200 mg) was added. After stirred at rt for 48h, the mixture was partitioned between ethyl acetate and 5% sodium bicarbonate. The organic phase was washed with brine, dried over sodium sulphate and concentrate in vacuo to give a yellow residue, which was purified with flash chromatography (methanol/DCM gradient elution). Off white amorphous powder was obtained. TLC single spot at Rf 0.38 (10% methanol/DCM) ; HPLC purity 99% (tR 2.0 min in 10% WATER-METHANOL) ;’H NMR (270 MHz, DMSO): 5 12.1 (1H, s, NH), 10.3 (1H, s, NH), 7.78 (1H, d, J = 7.9 Hz, ArH), 7.68 (1H, d, J= 7.9 Hz, ArH), 7.29-7. 35 (2H, m, ArH), 7.12 (1H, s, ArH), 6.83 (1H, dd, J= 8.4, 1.8 Hz, ArH), 2.63 (3H, s, CH3), 2.41 (3H, s, CH3) ; APCI-MS 334 (M-H+) ; FAB-HRMS calcd for C1SH1SCIN302S (MH+) 336.0573, found 336.0583.
Statistics shows that 2-Methyl-1H-benzoimidazol-5-ylamine is playing an increasingly important role. we look forward to future research findings about 29043-48-9.
Reference:
Patent; STERIX LIMITED; WO2004/37251; (2004); A1;,
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