Sodium Iodide → HCID 178433442, compound

HRID 1399186Notes

Reaction equation

HRID 1399186 reaction equation
[Cl:1][C:2]1[C:10]2[N:9]=[C:8]3[N:11]([C:15]4[C:16]([CH3:23])=[N:17][C:18]([O:21]C)=[CH:19][CH:20]=4)[CH2:12][CH2:13][CH2:14][N:7]3[C:6]=2[C:5]([CH:24]([O:29][CH:30]([F:32])[F:31])[C:25]([F:28])([F:27])[F:26])=[CH:4][CH:3]=1.[I-].[Na+].C[Si](Cl)(C)C>C(#N)C>[Cl:1][C:2]1[C:10]2[N:9]=[C:8]3[N:11]([C:15]4[CH:20]=[CH:19][C:18]([OH:21])=[N:17][C:16]=4[CH3:23])[CH2:12][CH2:13][CH2:14][N:7]3[C:6]=2[C:5]([CH:24]([O:29][CH:30]([F:31])[F:32])[C:25]([F:28])([F:27])[F:26])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 5238Sodium Iodide2×HCID 6397Chlorotrimethylsilane2×HCID 44156254HCID 44156254, compound

Product 1

HCID 178433442HCID 178433442, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 9-chloro-6-[1-(difluoromethoxy)-2,2,2-trifluoroethyl]-1-(6-methoxy-2-methylpyridin-3-yl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazole (152.2 mg, 0.319 mmol) in acetonitrile (3.0 mL) were added sodium iodide (143.5 mg, 0.958 mmol) and trimethylsilyl chloride (121.6 μL, 0.958 mmol). The mixture was stirred at room temperature for 1 day. To the mixture were added sodium iodide (71.8 mg, 0.479 mmol) and trimethylsilyl chloride (60.8 μL, 0.479 mmol). The mixture was stirred at room temperature for 3 hrs. The mixture was quenched with aqueous saturated ammonium chloride and extracted with ethyl acetate (×3). The combined organic layer was washed with water (×2) and brine (×1), dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with a 10% methanol/ethyl acetate gradient mixture to give the title compound as a colorless amorphous (119.8 mg, 0.259 mmol, 81%).

Workup

  1. stirringThe mixture was stirred at room temperature for 3 hrs
  2. customThe mixture was quenched with aqueous saturated ammonium chloride
  3. extractionextracted with ethyl acetate (×3)
  4. washThe combined organic layer was washed with water (×2) and brine (×1)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by silica gel column chromatography
  9. washeluting with a 10% methanol/ethyl acetate gradient mixture

Sources & evidence

ORD record
ord-8387cf038f214983b9231fc1c3a74582
Source dataset
uspto-grants-2014_12
Patent number
US08901141B2

Reaction notes

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