Imidazole → HCID 90449939, compound

HRID 1411259Notes

Reaction equation

HRID 1411259 reaction equation
[NH2:1][C:2]1[S:3][C:4]([S:7][CH:8]([CH3:11])[CH2:9][OH:10])=[CH:5][N:6]=1.N1C=CN=C1.[Si:17](Cl)([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18]>CN(C)C=O.O>[Si:17]([O:10][CH2:9][CH:8]([S:7][C:4]1[S:3][C:2]([NH2:1])=[N:6][CH:5]=1)[CH3:11])([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 90449618HCID 90449618, compound

Product 1

HCID 90449939HCID 90449939, compoundYield 87.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

2-((2-Aminothiazol-5-yl)thio)propan-1-ol (101 mg, 0.53 mmol) was dissolved in N,N-dimethylformamide (5 mL). Thereafter, imidazole (72 mg, 1.06 mmol) and t-butyldimethylsilyl chloride (100 mg, 0.64 mmol) were added to the above obtained solution, and the thus obtained mixture was then stirred at room temperature for 14.5 hours. Thereafter, the reaction solution was diluted with water, and was then extracted with ethyl acetate. The organic layer was washed with water and brine, and was then dried over anhydrous magnesium sulfate, followed by concentration in vacuo. The obtained residue was purified by preparative thin-layer chromatography (chloroform:methanol=10:1) to obtain 5-((1-((t-butyldimethylsilyl)oxy)propan-2-yl)thio) thiazole-2-amine (141 mg, 87%) in the form of a yellow oily product.

Workup

  1. extractionwas then extracted with ethyl acetate
  2. washThe organic layer was washed with water and brine
  3. dry with materialwas then dried over anhydrous magnesium sulfate
  4. concentrationfollowed by concentration in vacuo
  5. customThe obtained residue was purified by preparative thin-layer chromatography (chloroform:methanol=10:1)

Sources & evidence

ORD record
ord-2989d1589b884475b109e2e745916ddf
Source dataset
uspto-grants-2014_12
Patent number
US08921576B2

Reaction notes

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