Hydrochloric Acid → HCID 75593293, compound

Tert-butyl 4-(5,6-dibromo-4-nitro-1H-1,3-benzodiazol-2-yl)piperazine-1-carboxylate (Method 4A) (0.4 mmol, 200 mg) was dissolved in acetonitrile (5 ml). Next, NaOH (0.5 mmol, 19 mg) was added. The mixture was stirred at RT for 0.5 h. Then 2-Iodopropane (32 mmol, 538 mg) was added dropwise. The resulting mixture was stirred at 85° C. in a sealed tube until the reaction was complete (18 hours) by LC/MS. The mixture was allowed to cool to RT and concentrated in-vacuo. The product was taken up into ethyl acetate and washed with water. The organic extract was dried over MgSO4, filtered and concentrated. The product was purified on silica gel using EA/hex (1:4). The obtained product (0.3 mmol, 180 mg) was dissolved in MeOH (3 ml), then hydrogen chloride, (4M in 1,4-dioxane, 1 ml) was added dropwise. The resulting mixture was stirred at RT overnight. Solid was filtered and washed with Et2O to afford 5,6-dibromo-4-nitro-2-(piperazin-1-yl)-1-(propan-2-yl)-1H-1,3-benzodiazole hydrochloride (130 mg). 1H NMR (600 MHz, DMSO) δ 9.37 (s, 2H), 8.28 (s, 1H), 4.62 (hept, J=6.9 Hz, 1H), 3.47-3.44 (m, 4H), 3.28-3.26 (m, 4H), 1.54 (d, J=6.9 Hz, 6H); m/z 472; rt 2.4.

1. stirringThe resulting mixture was stirred at 85° C. in a sealed tube until the reaction
2. custom(18 hours)
3. temperatureto cool to RT
4. concentrationconcentrated in-vacuo
5. washwashed with water
6. extractionThe organic extract
7. dry with materialwas dried over MgSO4
8. filtrationfiltered
9. concentrationconcentrated
10. customThe product was purified on silica gel
11. stirringThe resulting mixture was stirred at RT overnight
12. filtrationSolid was filtered
13. washwashed with Et2O

ORD record

ord-3a28178d353940fabd3e98ff380ea79e

Source dataset

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09388192B2