Sodium hydride → HCID 11951781, compound

HRID 2101507Notes

Reaction equation

HRID 2101507 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]=[C:13]([Cl:15])[CH:14]=1)[CH2:5][N:6]1[CH:10]=[CH:9][N:8]=[C:7]1[NH2:11].[H-].[Na+].[CH3:18][O:19][C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][CH:27]=1)[CH2:23]Br>CN(C=O)C.CCOC(C)=O>[Cl:15][C:13]1[CH:12]=[C:4]([CH:3]=[C:2]([Cl:1])[CH:14]=1)[CH2:5][N:6]1[CH:10]=[CH:9][N:8]=[C:7]1[NH:11][CH2:23][C:22]1[CH:25]=[CH:26][CH:27]=[C:20]([O:19][CH3:18])[CH:21]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 40672073-Methoxybenzyl bromideHCID 57801504HCID 57801504, compound

Product 1

HCID 11951781HCID 11951781, compoundYield 5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-(3,5-Dichloro-benzyl)-1H-imidazol-2-ylamine (see Example 12) was dissolved in anhydrous DMF and NaH was added to the solution under H2. The reaction mixture was stirred at room temperature for 10 min and 3-methoxybenzylbromide was added. The reaction mixture was stirred at 65° C. for 5 h. The reaction mixture was then diluted with EtOAc and washed with water (×5). The organic phase was dried over Na2SO4 and concentrated. The resulting residue was purified by silica gel preparative TLC using CH2Cl2:MeOH 95:5 to afford the title compound (7 mg, 5%); LCMS m/z 362 [C18H17Cl2N3O+H]+.

Workup

  1. stirringThe reaction mixture was stirred at 65° C. for 5 h
  2. washwashed with water (×5)
  3. dry with materialThe organic phase was dried over Na2SO4
  4. concentrationconcentrated
  5. customThe resulting residue was purified by silica gel preparative TLC

Sources & evidence

ORD record
ord-72ffbc1f9b454d43bd5a8bb67bf8dd17
Source dataset
uspto-grants-2009_08
Patent number
US07572921B2

Reaction notes

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