Sodium Iodide → HCID 178469371, compound

HRID 732454Notes

Reaction equation

HRID 732454 reaction equation
[I-].[Na+].[CH2:3]([O:5][C:6](=[O:20])[C:7]1[CH:12]=[C:11]([O:13]C)[N:10]=[C:9]([NH:15][C@H:16]([CH2:18][CH3:19])[CH3:17])[CH:8]=1)[CH3:4].Cl[Si](C)(C)C>C(#N)C>[CH2:3]([O:5][C:6](=[O:20])[C:7]1[CH:12]=[C:11]([OH:13])[N:10]=[C:9]([NH:15][C@H:16]([CH2:18][CH3:19])[CH3:17])[CH:8]=1)[CH3:4]

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 68815378(S)-2-sec-Butylamino-6-methoxy-isonicotinic acid ethyl ester

Product 1

HCID 178469371HCID 178469371, compoundYield 56.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Treat sodium iodide (5.58 g, 36.7 mmol) and (S)-2-sec-butylamino-6-methoxy-isonicotinic acid ethyl ester (1.85 g, 7.3 mmol) in acetonitrile (30 mL) with chlorotrimethylsilane (4.66 mL, 36.7 mmol) and stir at reflux for 38 h. Quench with methanol (10 mL), stir for 24 h, and concentrate. Dissolve residue in ethyl acetate, wash with water, saturated aqueous sodium chloride, dry (magnesium sulfate), concentrate and purify (silica gel chromatography, eluting with 70:30 to 100:0 ethyl acetate:hexanes) to give the title compound (0.98 g, 56%).

Workup

  1. temperatureat reflux for 38 h
  2. customQuench with methanol (10 mL)
  3. stirringstir for 24 h
  4. concentrationconcentrate
  5. washDissolve residue in ethyl acetate, wash with water, saturated aqueous sodium chloride
  6. dry with materialdry (magnesium sulfate)
  7. concentrationconcentrate
  8. custompurify
  9. wash(silica gel chromatography, eluting with 70:30 to 100:0 ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-29707200eb9d4f8fbb011f5f1a90d45b
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Reaction notes

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