Water → HCID 58626007, compound

Participants

Reaction Conditions

Reaction Steps

Stir 3-amino-1,5-dihydro-benzo[b][1,4]diazepine-2,4-dione (10.0 g, 52.3 mmol) as a tan colored slurry in THF (300 mL) at 0-3° C. under nitrogen. Add triethylamine (8.00 mL, 57.0 mmol) in one portion. Add dropwise isobutyryl chloride (6.00 mL, 57.0 mmol) keeping the temperature below 3° C. Stir the resulting light yellow colored slurry at 0-3° C. for 3.5 hours until complete reaction by HPLC. Add deionized water (450 mL) over 15-20 minutes, keeping the pot temperature below 10° C. After stirring at 0-10° C. for 1.5 hours, isolate the product by filtration, rinse with cold (0-3° C.) 2:1/Water:THF (50 mL), then water (50 mL). Dry the solid in a vacuum oven at 50° C. to afford 10.5 g (77%) of the title compound: 1H NMR (500 MHz, DMSO-d6) δ 10.7 (s, 2H), 8.15 (d, 1H), 7.2 (m, 4H), 4.7 (d, 1H), 2.75 (m, 1H), 1.0 (s, 6H).

Provenance & Evidence