Methyl iodide → Methyl 4-[(5,6-dichloro-2-{[4-(methoxy)-phenyl]imino}-3-methyl-2,3-dihydro-1h-benzimidazol-1-yl)methyl]benzoate

HRID 1594521Notes

Reaction equation

HRID 1594521 reaction equation
[Cl:1][C:2]1[C:30]([Cl:31])=[CH:29][C:5]2[N:6]([CH2:18][C:19]3[CH:28]=[CH:27][C:22]([C:23]([O:25][CH3:26])=[O:24])=[CH:21][CH:20]=3)[C:7]([NH:9][C:10]3[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=3)=[N:8][C:4]=2[CH:3]=1.[H-].[Na+].CI.[CH2:36](Cl)Cl>CN(C=O)C.CCOC(C)=O>[Cl:1][C:2]1[C:30]([Cl:31])=[CH:29][C:5]2[N:6]([CH2:18][C:19]3[CH:28]=[CH:27][C:22]([C:23]([O:25][CH3:26])=[O:24])=[CH:21][CH:20]=3)[C:7](=[N:9][C:10]3[CH:11]=[CH:12][C:13]([O:16][CH3:17])=[CH:14][CH:15]=3)[N:8]([CH3:36])[C:4]=2[CH:3]=1

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 6344DichloromethaneHCID 24758Sodium hydrideHCID 69417835Methyl 4-[(5,6-dichloro-2-{[4-(methoxy)-phenyl]amino}-1h-benzimidazol-1-yl)methyl]benzoate

Product 1

HCID 69418089Methyl 4-[(5,6-dichloro-2-{[4-(methoxy)-phenyl]imino}-3-methyl-2,3-dihydro-1h-benzimidazol-1-yl)methyl]benzoate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the title compound of Example 19, Step B (0.45 mmol, 203 mg) in DMF (3 mL) was added NaH (0.54 mmol, 21 mg of 60% suspension in mineral oil). After 10 min MeI (0.9 mmol, 56 μL) was added and the reaction was allowed to stand at ambient temperature for 2 h. Aqueous workup with CH2Cl2/saturated NaHCO3, followed by flash chromatography on silica eluting with 30% and 40% EtOAc in hexanes, afforded the product as a white solid. LC-MS (ESI, Method B): 1.93 min. m/z 470.2 (M+1).

Sources & evidence

ORD record
ord-54602a73e44a40199a32c2e4e6427d98
Source dataset
uspto-grants-2007_11
Patent number
US07301036B2

Reaction notes

Loading…