Sodium Cyanate → Acetamide, N-[2-[5-[(aminocarbonyl)amino]-1H-indol-3-yl]ethyl]-

HRID 1581721Notes

Reaction equation

HRID 1581721 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][CH2:12][NH:13][C:14](=[O:16])[CH3:15].[O-:17][C:18]#[N:19].[Na+]>C(O)(=O)C.O>[NH:1]([C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][CH2:12][NH:13][C:14](=[O:16])[CH3:15])[C:18]([NH2:19])=[O:17]

Participants

4

Reactant 2

HCID 517096Sodium CyanateHCID 22722278N-[2-(5-Amino-1H-indol-3-yl)ethyl]acetamide

Product 1

HCID 9921407Acetamide, N-[2-[5-[(aminocarbonyl)amino]-1H-indol-3-yl]ethyl]-

Reagents, catalysts & solvents 1

HCID 21899381Acetic acid--water (1/1)Solvent

Procedure

The product from Example 3 is dissolved in acetic acid-water (1:2, 3 mL) and sodium cyanate (2 mmol) added. This is stirred until a brownish gum is precipitated. The mixture is extracted with chloroform (3×30 mL), and the organic extracts washed with saturated sodium bicarbonate, dried with magnesium sulfate and the solvent evaporated in vacuo. The resulting product is purified by reverse-phase HPLC as above.

Workup

  1. customis precipitated
  2. extractionThe mixture is extracted with chloroform (3×30 mL)
  3. washthe organic extracts washed with saturated sodium bicarbonate
  4. dry with materialdried with magnesium sulfate
  5. customthe solvent evaporated in vacuo
  6. customThe resulting product is purified by reverse-phase HPLC as above

Sources & evidence

ORD record
ord-e4e172bd19b7412ea2fd4e45eab4f2ee
Source dataset
uspto-grants-2004_05
Patent number
US06730707B2

Reaction notes

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