Imidazole → HCID 86723179, compound

HRID 1050298Notes

Reaction equation

HRID 1050298 reaction equation
[C:1]([CH2:3][CH2:4][N:5]1[CH2:13][C@H:12]([OH:14])[CH2:11][C@H:6]1[C:7]([O:9]C)=O)#[N:2].N1C=CN=C1.[CH2:20]([Si:22](Cl)([CH2:25][CH3:26])[CH2:23][CH3:24])[CH3:21]>CN(C)C=O>[CH2:20]([Si:22]([CH2:25][CH3:26])([CH2:23][CH3:24])[O:14][C@H:12]1[CH2:13][N:5]2[CH2:4][CH2:3][CH2:1][NH:2][C:7](=[O:9])[C@@H:6]2[CH2:11]1)[CH3:21]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 13819ChlorotriethylsilaneHCID 86723178HCID 86723178, compound

Product 1

HCID 86723179HCID 86723179, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the product from Example 1, Part B (0.33 g, 1.94 mmol) in anhydrous N,N-dimethylformamide (10 mL) was added imidazole (0.264 g, 3.88 mmol) and triethylsilyl chloride (0.488 mL, 2.91 mmol). The resulting solution was stirred at room temperature for 16 hours. The mixture was partitioned between ethyl acetate (50 mL) and water (2×50 mL), and the organic extract was dried over Na2SO4. The drying agent was removed by filtration, and the filtrate was concentrated in vacuo to give a crude product that was purified by column chromatography on silica gel using a solvent gradient of 0-10% methanol in dichloromethane. The title compound was obtained as a colorless solid (0.28 g, 51%).

Workup

  1. customThe mixture was partitioned between ethyl acetate (50 mL) and water (2×50 mL)
  2. extractionthe organic extract
  3. dry with materialwas dried over Na2SO4
  4. customThe drying agent was removed by filtration
  5. concentrationthe filtrate was concentrated in vacuo
  6. customto give a crude product that
  7. customwas purified by column chromatography on silica gel using a solvent gradient of 0-10% methanol in dichloromethane

Sources & evidence

ORD record
ord-52dd2e596326453d8bd1792603997586
Source dataset
uspto-grants-2016_07
Patent number
US09382258B2

Reaction notes

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