Triethylamine → HCID 178455182, compound

HRID 1162322Notes

Reaction equation

HRID 1162322 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][CH2:15][C:16]2[N:17]=[C:18]([CH2:21][OH:22])[NH:19][CH:20]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:30]([Si:34]([CH3:37])([CH3:36])Cl)([CH3:33])([CH3:32])[CH3:31]>ClCCl.C(Cl)(Cl)Cl.O>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][CH2:15][C:16]2[N:17]=[C:18]([CH2:21][O:22][Si:34]([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:37])[CH3:36])[NH:19][CH:20]=2)[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 178519989HCID 178519989, compound

Product 1

HCID 178455182HCID 178455182, compoundYield 52%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of (4-(((1-benzyl-4-piperidinyl)amino)methyl)-1H-imidazol-2-yl)methanol (0.28 g) obtained in Example 83f) and triethylamine (0.26 ml) in dichloromethane (5 ml) was added tert-butyl dimethylchlorosilane (0.17 g), and mixed at room temperature for 3 hours. The reaction solution was diluted with chloroform and water. The organic layer was collected by separation, washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified with basic silica gel column (ethyl acetate:ethanol=10:1) to obtain the title compound as a pale yellow oil (0.20 g, 52%).

Workup

  1. additionmixed at room temperature for 3 hours
  2. customThe organic layer was collected by separation
  3. washwashed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe residue was purified with basic silica gel column (ethyl acetate:ethanol=10:1)

Sources & evidence

ORD record
ord-6fe5ba88f81d4d00a1dbabf69c96a8c4
Source dataset
uspto-grants-2010_10
Patent number
US07820673B2

Reaction notes

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