Sodium Iodide → HCID 178469371, compound

HRID 1436598Notes

Reaction equation

HRID 1436598 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-21ef2134c200421a91fbfa56a0b64391
Source dataset
uspto-grants-2009_11
Patent number
US07618978B2

Reaction notes

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