Methyl iodide → HCID 59485595, compound

HRID 1972192Notes

Reaction equation

HRID 1972192 reaction equation
[Cl:1][C:2]1[CH:27]=[CH:26][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([N:13]3[C@@H:17]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[C:16](=[O:24])[NH:15][C:14]3=[O:25])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.[C:28]([O-])([O-])=O.[K+].[K+].CI>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][C:7]2[CH:8]=[CH:9][C:10]([N:13]3[C@@H:17]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[C:16](=[O:24])[N:15]([CH3:28])[C:14]3=[O:25])=[CH:11][CH:12]=2)=[CH:26][CH:27]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 59485753HCID 59485753, compound

Product 1

HCID 59485595HCID 59485595, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-[4-(4-chloro-phenoxy)-phenyl]-5-(S)-phenyl-imidazolidine-2,4-dione (10.0 mg, 0.026 mmol) in anhydrous DMF (0.5 mL) are added K2CO3 (7.3 mg, 0.052 mmol) and MeI (4.93 μL, 0.078 mmol). The reaction mixture is stirred at room temperature overnight before removal of the solvent. The residue is purified by preparative LC/MC to provide the title compound; 1H NMR (CDCl3, 400 MHz) δ 7.42-7.31 (m, 7H), 7.26 (d, 2H), 6.90 (m, 4H), 5.42 (s, 1H), 3.16 (s, 3H); HPLC-MS calculated for C22H17ClN2O3 (M+H+) 393.1, found 393.1.

Workup

  1. customThe residue is purified by preparative LC/MC

Sources & evidence

ORD record
ord-10527511ec89446bb0422c93ec43eaaa
Source dataset
uspto-grants-2013_04
Patent number
US08431607B2

Reaction notes

Loading…