Imidazole → HCID 18442799, compound

HRID 546438Notes

Reaction equation

HRID 546438 reaction equation
[C:1]([Si:5](Cl)([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)([CH3:4])([CH3:3])[CH3:2].N1C=CN=C1.[CH3:24][C:25]([N:29]1[CH2:34][CH2:33][C:32]2[N:35]=[CH:36][S:37][C:31]=2[CH2:30]1)([CH3:28])[CH2:26][OH:27].O>CN(C)C=O.C(OCC)C>[Si:5]([O:27][CH2:26][C:25]([N:29]1[CH2:34][CH2:33][C:32]2[N:35]=[CH:36][S:37][C:31]=2[CH2:30]1)([CH3:24])[CH3:28])([C:1]([CH3:4])([CH3:3])[CH3:2])([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

7

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 94078tert-ButyldiphenylchlorosilaneHCID 17842364HCID 17842364, compound

Product 1

HCID 18442799HCID 18442799, compoundYield 93.5%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

tert-Butylchlorodiphenylsilane (1.93 g) and imidazole (994 mg) were added to a solution of 5-(1,1-dimethyl-2-hydroxyethyl)-4,5,6,7-tetrahydrothiazolo-[5,4-c]pyridine (1.24 g) in N,N-dimethylformamide (5 ml) at room temperature, and the mixture was stirred overnight. Water and diethyl ether were added to the reaction mixture to separate an organic layer. The organic layer was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by column chromatography on silica gel (hexane:ethyl acetate=1:2) to obtain the title compound (2.46 g) as a colorless oil.

Workup

  1. customto separate an organic layer
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. distillationThe solvent was distilled off under reduced pressure
  4. customthe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=1:2)

Sources & evidence

ORD record
ord-d7b37d877e744da6a837462bfa9d9fd3
Source dataset
uspto-grants-2011_05
Patent number
US07935824B2

Reaction notes

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