Methyl iodide → HCID 24755556, compound

HRID 1869791Notes

Reaction equation

[Cl:1][C:2]1[CH:33]=[CH:32][CH:31]=[C:30]([Cl:34])[C:3]=1[CH2:4][NH:5][CH:6]([CH2:11][C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][CH:21]=1)[N:18]=[C:17]([C:22]1[C:27]([Cl:28])=[CH:26][CH:25]=[CH:24][C:23]=1[Cl:29])[CH:16]=[CH:15]2)[C:7]([O:9][CH3:10])=[O:8].[C:35]([O-])(O)=O.[Na+].CI>CO>[Cl:1][C:2]1[CH:33]=[CH:32][CH:31]=[C:30]([Cl:34])[C:3]=1[CH2:4][N:5]([CH3:35])[CH:6]([CH2:11][C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][CH:21]=1)[N:18]=[C:17]([C:22]1[C:27]([Cl:28])=[CH:26][CH:25]=[CH:24][C:23]=1[Cl:29])[CH:16]=[CH:15]2)[C:7]([O:9][CH3:10])=[O:8]

Participants

Conditions

Temperature: 0 °C

Procedure

To 100 mg of (methyl 2-[(2,6-dichlorobenzyl)amino]-3-[2-(2,6-dichlorophenyl)-6-quinolinyl]propanoate) 41 in CH3OH (2.3 ml) are added, at 0° C., NaHCO3 (1 equ.) and CH3I (1 equ.). The reaction is stirred for 1 h at 0° C., and then at room temperature for 2 days. The solvent is evaporated and CH2Cl2 (10 ml) is added to the residue. The solution is washed with water, brine, again water and dried over MgSO4, filtered and evaporated. Due to an incomplete reaction, the protocol is repeated using a tenfold excess of NaHCO3 and CH3I in MeOH (5 ml). After a similar work-up, the residue is purified by silica gel chromatography using hexane/AcOEt 90/10 as eluent to give methyl 2-[(2,6-dichlorobenzyl)(methyl)amino]-3-[2-(2,6-dichlorophenyl)-6-quinolinyl]propanoate 51.

Workup

waitat room temperature for 2 days
customThe solvent is evaporated
additionCH2Cl2 (10 ml) is added to the residue
washThe solution is washed with water, brine, again water
dry with materialdried over MgSO4
filtrationfiltered
customevaporated
customDue to an incomplete reaction
customAfter a similar work-up, the residue is purified by silica gel chromatography

Sources & evidence

ORD record: ord-f2e161a087fd4b46ab36c5cc124da5d0
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07638630B2

Reaction notes

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