2-Amino-5-methoxy-1-methylbenzimidazole synthesis
- Product Name:2-Amino-5-methoxy-1-methylbenzimidazole
- CAS Number:1805-02-3
- Molecular formula:C9H11N3O
- Molecular Weight:177.2
Yield:1805-02-3 70%
Reaction Conditions:
in methanol at 20; for 72 h;
Steps:
5-Methoxy-1-methyl-1H-benzo[d]imidazol-2-amine (42.01)
Cyanogen bromide (1.5 eq) was added to a solution of 4-methoxy-N1-methylbenzene-1,2-diamine (500 mg, 3.3 mmol) in MeOH (5 mL). the solution wasleft to stir at room temp over 72 h. The solution was boiled to remove MeOH andbasified with ammonia solution. The solution was filtered, concentrated and purifiedvia recrystallization to obtain the known title compound (410 mg, 70 %).(52) HPLC - tR 3.39 min > 99% purity at254 nm; LRMS [M+H]+ 178.0 m/z; 1H NMR (400 MHz, CDCl3) δ 6.98 - 6.94 (m, 2H), 6.71 (dd, J = 8.6, 2.3 Hz,1H), 3.82 (s, 3H), 3.55 (s, 3H); 13C NMR (101 MHz, CDCl3) δC 156.2, 153.6, 140.9, 128.8, 108.5, 108.1, 100.7,56.1, 29.1.
References:
McNamara, Nicole;Saunders, Eleanor;Varghese, Swapna;Zheng, Rebecca;Simpson, Kaylene;Varma, Devika M.;Johnson, Monica M.;Hasan Zahid, M Shamim;Bachelder, Eric M.;Ainslie, Kristy M.;No, Joo Hwan;Koh, Dahae;Shum, David;Das, Nirmal;Patra, Binita;Roy, Jayasree;Talukdar, Arindam;Ganguly, Dipyman;McConville, Malcolm;Baell, Jonathan [European Journal of Medicinal Chemistry,2022,vol. 240,art. no. 114577] Location in patent:supporting information
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1805-02-3
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1805-02-3
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