1-Chloroethyl chloroformate → HCID 117992657, compound

HRID 717083Notes

Reaction equation

ClC(OC(Cl)C)=O.[CH3:8][N:9](C)[CH2:10][CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[NH:20][C:21](=[O:30])[C:22]3[C:27]([CH:28]=2)=[C:26]([CH3:29])[CH:25]=[CH:24][CH:23]=3)=[CH:15][CH:14]=1>ClCCCl>[CH3:29][C:26]1[CH:25]=[CH:24][CH:23]=[C:22]2[C:27]=1[CH:28]=[C:19]([C:16]1[CH:15]=[CH:14][C:13]([O:12][CH2:11][CH2:10][NH:9][CH3:8])=[CH:18][CH:17]=1)[NH:20][C:21]2=[O:30]

Participants

Conditions

Temperature: 0 °C

Procedure

1-Chloro-ethyl chloroformate (97 mg, 0.68 mmol) in 1,2-dichloroethane (0.3 mL) was added to a solution of 3-[4-(2-dimethylamino-ethoxy)-phenyl]-5-methyl-2H-isoquinolin-1-one (35 mg, 0.109 mmol) in 1,2-dichloroethane (0.6 mL) at cooled to 0° C., and stirred for 10 min. The reaction mixture was irradiated using a microwave (300 W, 180° C., 15 min) then concentrated in vacuo and EtOH (0.8 mL) added. The reaction mixture was heated at 80° C. for 15 h, allowed to cool and passed through a SCX-2 cartridge (1 g), eluting with 0.5M NH3 in MeOH. The crude material was concentrated in vacuo and purified by reverse phase preparative HPLC-MS to afford 5-methyl-3-[4-(2-methylamino-ethoxy)-phenyl]-2H-isoquinolin-1-one as a white solid (4 mg, 12%).

Workup

customThe reaction mixture was irradiated
customa microwave (300 W, 180° C., 15 min)
concentrationthen concentrated in vacuo and EtOH (0.8 mL)
additionadded
temperatureThe reaction mixture was heated at 80° C. for 15 h
temperatureto cool
washeluting with 0.5M NH3 in MeOH
concentrationThe crude material was concentrated in vacuo
custompurified by reverse phase preparative HPLC-MS

Sources & evidence

ORD record: ord-78e074bfd33e4936a26cf8bfc5b98e76
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09193689B2

Reaction notes

Loading…