2-Imidazolidinone → HCID 16059505, compound

HRID 1710637Notes

Reaction equation

Cl[CH2:2][C:3]([N:5]1[CH2:10][CH2:9][N:8]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([O:18][CH3:19])[CH:12]=2)[CH2:7][CH2:6]1)=[O:4].[NH:20]1[CH2:24][CH2:23][NH:22][C:21]1=[O:25].C([O-])([O-])=O.[K+].[K+]>CN1C(=O)CCC1>[Cl:17][C:14]1[CH:15]=[CH:16][C:11]([N:8]2[CH2:9][CH2:10][N:5]([C:3](=[O:4])[CH2:2][N:20]3[CH2:24][CH2:23][NH:22][C:21]3=[O:25])[CH2:6][CH2:7]2)=[CH:12][C:13]=1[O:18][CH3:19]

Participants

Conditions

Temperature: 60 °C

Procedure

In a 4 mL vial was added 2-chloro-1-[4-(4-chloro-3-methoxy-phenyl)-piperazin-1-yl]-ethanone (1) (200 mg, 0.66 mmol, 1.0 equiv), imidazolidin-2-one (64 mg, 0.73 mmol, 1.10 equiv), K2CO3 (365 mg, 2.64 mmol, 4.0 equiv) and 2.4 mL of NMP. A stir bar was placed in the vial and the vial was then capped. The mixture stirred at 60° C. overnight. The crude product was purified by reversed phase HPLC (acetonitrile —H2O with 0.1% TFA as the eluent) to yield 1-{2-[4-(4-chloro-3-methoxy-phenyl)-piperazin-1-yl]-2-oxo-ethyl}-imidazolidin-2-one (22): HPLC retention time, 1.33 minutes (Agilent Zorbax SB-C18, 2.1×50 mm, 5μ, 35° C.) using 1 ml/min flow rate, a 2.5 minute gradient of 20% to 100% B with a 1.1 minute wash at 100% B (A=0.1% formic acid/5% acetonitrile/94.9% water, B=0.1% formic acid/5% water/94.9% acetonitrile); MS (ES) M+H expected, 352.8, found, 353.5.

Workup

customA stir bar was placed
customin the vial and the vial was then capped
customThe crude product was purified by reversed phase HPLC (acetonitrile —H2O with 0.1% TFA as the eluent)

Sources & evidence

ORD record: ord-5596ee2ba4f04a46a68c26fd63c6e6af
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07790726B2

Reaction notes

Loading…