5-Amino-1,3-dihydro-2H-benzimidazol-2-one

Chemical Properties

Crystalline powder

Uses

5-Amino-2-hydroxybenzimidazole is an important reagent in the discovery of potent and selective non-nucleotide small molecule inhibitors of CD73

Synthesis

Step: 21b Synthesis of 5-amino-1,3-dihydrobenzimidazol-2-one. Pd/C catalyst (140 mg) was added to a mixed solution of methanol and ethyl acetate containing 5-nitro-1,3-dihydrobenzimidazol-2-one (1.4 g, 7.8 mmol) and the hydrogenation reaction was carried out for 6 hours. The progress of the reaction was monitored by thin layer chromatography (TLC, the unfolding agent was a chloroform solution of 10% methanol). After completion of the reaction, the reaction mixture was filtered through a bed of diatomaceous earth and the filtrate was concentrated to give the target product 5-amino-1,3-dihydrobenzimidazol-2-one (1 g, 86% yield).

References

[1] Patent: WO2012/59932, 2012, A1. Location in patent: Page/Page column 161-162
[2] Patent: WO2009/42907, 2009, A1. Location in patent: Page/Page column 78-79
[3] Journal of the American Chemical Society, 1958, vol. 80, p. 1662
[4] Patent: WO2012/115479, 2012, A2. Location in patent: Page/Page column 23
[5] Patent: CN104151251, 2017, B. Location in patent: Paragraph 0024