Acetohydrazide → HCID 68298139, compound

Participants

Reaction Steps

In a 10 mL round bottomed flask, 9-Methyl-6-[4-(2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)piperidin-1-yl]-9H-purine-8-carboxylic acid (185 mg, 0.51 mmol, 1 equiv) and HATU (290 mg, 0.76 mmol, 1.5 equiv) were suspended anhydrous DMA (2 mL). Diisopropylethylamine (175 μL, 1.0 mmol, 2 equiv) followed by acetic hydrazide (45 mg, 0.61 mmol, 1.2 equiv) were added and the reaction stirred at room temperature overnight. The reaction mixture was diluted with ethyl acetate (20 mL), and the extracted with water (20 mL), and aqueous hydrochloric acid solution (0.1 M, 40 mL). The combined aqueous layers were then neutralized to pH=7 with saturated aqueous sodium bicarbonate. The resulting precipitate was filtered off, washed with water (2 mL) and acetonitrile (1 mL) and air dried yielding 135 mg of N′-acetyl-9-methyl-6-[4-(2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)piperidin-1-yl]-9H-purine-8-carbohydrazide in 59% yield. 1H NMR (400 MHz, DMSO-d6) δ 10.82 (s, 1H), 9.91 (s, 1H), 8.29 (s, 1H), 7.18-7.08 (m, 1H), 6.87 (dt, 3H), 4.52 (t, 1H), 3.92 (d, 3H), 2.31 (s, 2H), 1.86 (s, 3H), 1.79 (d, 2H). MS (EI) for C21H23N9O3: 450 (MH+).

Provenance & Evidence