1-Chloroethyl chloroformate → HCID 66780871, compound

Temperature

0 °C

A solution of 7-bromo-4-(4-methoxybenzyl)-1,3,4,5-tetrahydropyrido[2,3-e][1,4]diazepin-2-one (3.37 g, 9.30 mmol) in dichloroethane (180 mL) was cooled in an ice bath and treated with ACE-Cl (1.1 mL, 10 mmol). After stirring at 0° C. under N2 for 30 min and then at room temperature for 30 min, the mixture was heated to reflux for 1 h. The mixture was allowed to cool and then concentrated to dryness. Purification by flash column chromatography (silica gel, CH2Cl2/MeOH, 99:1) gave a white solid. A portion of the solid (1.02 g, 2.93 mmol) was suspended in methanol (50 mL) and heated to reflux for 3 h. The mixture was allowed to cool and the solid was isolated by filtration, washed with MeOH and dried under vacuum at 50° C. overnight to give the title compound (0.66 g, 46%) as a white solid: 1H NMR (300 MHz, DMSO-d6) δ 11.05 (s, 1H), 10.30 (br s, 2H), 8.57 (d, J=2.3 Hz, 1H), 8.15 (d, J=2.3 Hz, 1H), 4.24 (s, 2H), 3.79 (s, 2H); MS (ESI) m/e 242 (M+H)+.

1. waitat room temperature for 30 min
2. temperaturethe mixture was heated
3. temperatureto reflux for 1 h
4. temperatureto cool
5. concentrationconcentrated to dryness
6. customPurification by flash column chromatography (silica gel, CH2Cl2/MeOH, 99:1)
7. customgave a white solid
8. temperatureheated
9. temperatureto reflux for 3 h
10. temperatureto cool
11. customthe solid was isolated by filtration
12. washwashed with MeOH
13. customdried under vacuum at 50° C. overnight

ORD record

ord-4952b439f1c14c65950928aa372f2175

Source dataset

uspto-grants-2011_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07879872B2