Imidazole → HCID 23070816, compound

HRID 501452Notes

Reaction equation

HRID 501452 reaction equation
N1C=CN=C1.[C:6]([Si:10](Cl)([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([CH3:9])([CH3:8])[CH3:7].CN(C)C=O.[CH2:29]([N:33]1[C:37]([C:38](=[S:40])[NH2:39])=[C:36]([CH2:41][OH:42])[N:35]=[C:34]1[N:43]1[CH2:48][CH2:47][N:46]([C:49]([O:51][C:52]([CH3:55])([CH3:54])[CH3:53])=[O:50])[CH2:45][CH2:44]1)[C:30]#[C:31][CH3:32]>C(OCC)(=O)C>[Si:10]([O:42][CH2:41][C:36]1[N:35]=[C:34]([N:43]2[CH2:44][CH2:45][N:46]([C:49]([O:51][C:52]([CH3:55])([CH3:54])[CH3:53])=[O:50])[CH2:47][CH2:48]2)[N:33]([CH2:29][C:30]#[C:31][CH3:32])[C:37]=1[C:38](=[S:40])[NH2:39])([C:6]([CH3:9])([CH3:8])[CH3:7])([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 94078tert-ButyldiphenylchlorosilaneHCID 23070678HCID 23070678, compound

Product 1

HCID 23070816HCID 23070816, compoundYield 84.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

0.668 g of imidazole and 2.70 g of t-butylchlorodiphenylsilane were added to a 25 ml N,N-dimethylformamide solution of 3.221 g of t-butyl 4-[1-(2-butynyl)-4-hydroxymethyl-5-thiocarbamoyl-1H-imidazol-2-yl]piperazine-1-carboxylate, and the mixture was stirred at room temperature for 16 hours. 300 ml of ethyl acetate was added to the solution, and the organic layer was washed three times with 100 ml of water and then with 100 ml of a saturated sodium chloride solution. The organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography. Thus, 4.357 g of the title compound was obtained from the fraction eluted with ethyl acetate-hexane (2:3).

Workup

  1. washthe organic layer was washed three times with 100 ml of water
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-210d4399f62443f493822e621f2b4a98
Source dataset
uspto-grants-2010_08
Patent number
US07772226B2

Reaction notes

Loading…