Imidazole → 5-((tert-butyldimethylsilyloxy)methyl)-1-cyclohexyl-1H-benzo[d]imidazol-2-amine

HRID 2068303Notes

Reaction equation

HRID 2068303 reaction equation
[NH2:1][C:2]1[N:6]([CH:7]2[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)[C:5]2[CH:13]=[CH:14][C:15]([CH2:17][OH:18])=[CH:16][C:4]=2[N:3]=1.N1C=CN=C1.[Si:24](Cl)([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25]>CN(C)C=O.C(OCC)(=O)C>[Si:24]([O:18][CH2:17][C:15]1[CH:14]=[CH:13][C:5]2[N:6]([CH:7]3[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]3)[C:2]([NH2:1])=[N:3][C:4]=2[CH:16]=1)([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 67252967(2-Amino-1-cyclohexyl-1H-benzimidazol-5-yl)methanol

Product 1

HCID 672543375-((tert-butyldimethylsilyloxy)methyl)-1-cyclohexyl-1H-benzo[d]imidazol-2-amineYield 56.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (2-Amino-1-cyclohexyl-1H-benzoimidazol-5-yl)methanol (0.650 g, 0.00265 mol) and 1H-Imidazole (0.4149 g, 0.006094 mol) in N,N-Dimethylformamide (10 mL) was added tert-Butyldimethylsilyl chloride (0.4393 g, 0.002914 mol) and the mixture stirred for 1 hour. The mixture was diluted with ethyl acetate, washed with saturated socium bicarbonate, dried and concentrated. The residue was taken up in methylene chloride containing 0.1% triethylamine and purified by flash chromatography with a gradient of from 0 to 10 percent methanol. The product fractions were concentrated to give 539 mg of the product.

Workup

  1. washwashed with saturated socium bicarbonate
  2. customdried
  3. concentrationconcentrated
  4. custompurified by flash chromatography with a gradient of from 0 to 10 percent methanol
  5. concentrationThe product fractions were concentrated

Sources & evidence

ORD record
ord-d8047ff79d924f9f8da2960c99d734e7
Source dataset
uspto-grants-2012_10
Patent number
US08293923B2

Reaction notes

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