Imidazole → HCID 58488250, compound

HRID 2075413Notes

Reaction equation

HRID 2075413 reaction equation
[CH:1]([C@@H:4]1[C:9]([O:10][CH3:11])=[N:8][C@@H:7]([C@H:12]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=2)[OH:13])[C:6]([O:24][CH3:25])=[N:5]1)([CH3:3])[CH3:2].N1C=CN=C1.[C:31]([Si:35](Cl)([CH3:37])[CH3:36])([CH3:34])([CH3:33])[CH3:32]>C(Cl)Cl>[Si:35]([O:13][C@@H:12]([C:14]1[CH:19]=[CH:18][C:17]([C:20]([F:22])([F:21])[F:23])=[CH:16][CH:15]=1)[C@H:7]1[C:6]([O:24][CH3:25])=[N:5][C@H:4]([CH:1]([CH3:3])[CH3:2])[C:9]([O:10][CH3:11])=[N:8]1)([C:31]([CH3:34])([CH3:33])[CH3:32])([CH3:37])[CH3:36]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 57991912HCID 57991912, compound

Product 1

HCID 58488250HCID 58488250, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (S)-((2S,5R)-5-isopropyl-3,6-dimethoxy-2,5-dihydropyrazin-2-yl)(4-(trifluoromethyl)phenyl)methanol (3.5 g, 9.8 mmol), and imidazole (0.8 g, 11.8 mmol) in CH2Cl2 (50 mL) was added tert-butylchlorodimethylsilane (1.6 g, 10.4 mmol) and TEA (1.6 mL, 11.8 mmol) at room temperature. The mixture was stirred over the weekend. The mixture was diluted with DCM and washed with water, saturated NaHCO3, and brine. The organic layer was dried over Na2SO4 and concentrated in vacuo. The crude residue was purified by chromatography on silica gel (40-50% DCM-hexane) to provide the product as a white solid (3.4 g, 74%). LCMS (API-ES) m/z: 473 (M+H+).

Workup

  1. washwashed with water, saturated NaHCO3, and brine
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe crude residue was purified by chromatography on silica gel (40-50% DCM-hexane)

Sources & evidence

ORD record
ord-34ebdca31213423780f2bcabf43c64a8
Source dataset
uspto-grants-2011_04
Patent number
US07919504B2

Reaction notes

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