Imidazole → HCID 2734831, compound

HRID 857085Notes

Reaction equation

HRID 857085 reaction equation
N1[CH:5]=[CH:4][N:3]=C1.[Si](Cl)([C:9]([CH3:12])([CH3:11])[CH3:10])(C)C.[OH2:14].C[N:16]([CH3:19])[CH:17]=[O:18]>>[C:9]([O:18][C:17]([NH:16][C@@H:19]([CH2:10][CH:9]([CH3:12])[CH3:11])[CH2:5][C:4]#[N:3])=[O:14])([CH3:12])([CH3:11])[CH3:10]

Participants

5

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 6228DimethylformamideHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 2734831HCID 2734831, compound

Procedure

To a solution of the compound prepared in Reference Example 3 (2.04 g) in N,N-dimethylformamide (15 ml) were added imidazole (1.26 g) and t-butyldimethylsilylchloride (2.79 g) and the mixture was stirred for 3 hours at room temperature. To the reaction mixture was added water and was extracted with ethyl acetate. The organic layer was washed with water, saturated aqueous solution of sodium chloride and dried and concentrated. The residue was purified by column chromatography on silica gel (n-hexane:ethyl acetate=19:1) to give the title compound (3.06 g) having the following physical data.

Workup

  1. extractionwas extracted with ethyl acetate
  2. washThe organic layer was washed with water, saturated aqueous solution of sodium chloride
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography on silica gel (n-hexane:ethyl acetate=19:1)

Sources & evidence

ORD record
ord-26dd353835d1430a81023b8c74365bff
Source dataset
uspto-grants-2006_12
Patent number
US07144901B2

Reaction notes

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