Hydrochloric Acid → 10-Bromo-5H-benzo[f][1,2,4]triazolo[1,5-d][1,4]diazepin-6(7H)-one

Temperature

11 °C

A solution of 4-bromo-2-(2H-[1,2,4]triazol-3-yl)-phenylamine (25.0 g, 105 mmol) in dioxane (870 mL) and pyridine (10.0 mL) was cooled to 12° C. A solution of chloroacetyl chloride (9.56 mL, 121 mmol) in diethylether (34.7 mL) was added dropwise over a period of 8 min. The mixture was stirred at 10-12° C. for 75 min and treated within 5 min with aq NaOH 2N (126 mL, 251 mmol). The mixture was stirred for 17.5 h at ambient temperature. The pH thereby dropped to about pH=9 and it was adjusted to pH=8 with 3N HCl (6 mL). After evaporation the residue was stirred at 15° C. for 30 min in water (650 mL) and ethyl acetate (22 mL). The crystals were filtered off, washed with cold water and dried in vacuo. Trituration in ethyl acetate (100 mL) afforded the title compound (13.4 g, 46%) as a light yellow solid. MS: m/e=279.0/281.0 (M+H+).

1. stirringThe mixture was stirred for 17.5 h at ambient temperature
2. additionThe pH thereby dropped to about pH=9 and it
3. customAfter evaporation the residue
4. stirringwas stirred at 15° C. for 30 min in water (650 mL)
5. filtrationThe crystals were filtered off
6. washwashed with cold water
7. customdried in vacuo

ORD record

ord-c5e1387351b5419999052991a6062f92

Source dataset

uspto-grants-2009_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07514426B2