Water → HCID 11785015, compound

HRID 1358492Notes

Reaction equation

HRID 1358492 reaction equation
[Si:1]([O:8][CH2:9][C@H:10]([N:23]1[CH:27]=[C:26]([C:28]([NH2:30])=[O:29])[N:25]=[CH:24]1)[CH2:11][CH2:12][N:13]1[C:21]2[C:16](=[CH:17][CH:18]=[C:19]([OH:22])[CH:20]=2)[CH:15]=[CH:14]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].I[CH2:38][CH2:39][CH2:40][CH3:41].O>CN(C=O)C>[CH2:38]([O:22][C:19]1[CH:20]=[C:21]2[C:16]([CH:15]=[CH:14][N:13]2[CH2:12][CH2:11][C@@H:10]([N:23]2[CH:27]=[C:26]([C:28]([NH2:30])=[O:29])[N:25]=[CH:24]2)[CH2:9][O:8][Si:1]([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:2])[CH3:3])=[CH:17][CH:18]=1)[CH2:39][CH2:40][CH3:41]

Participants

6

Reactant 4

HCID 962WaterHCID 10962Butyl iodideHCID 11430Potassium CarbonateHCID 11373744HCID 11373744, compound

Product 1

HCID 11785015HCID 11785015, compoundYield 73.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Under N2, to a solution of 1-[(R)-1-(tert-butyldimethylsilyloxy)-4-(6-hydroxyindol-1-yl)-2-butyl]imidazole-4-carboxamide (80 mg, 0.187 mmol) in DMF (5 ml) was added potassium carbonate (38.7 mg, 0.280 mmol) at room temperature. The reaction mixture was stirred for 30 minutes. And then 1-iodobutane (51.5 mg, 0.280 mmol) was added and the resulting mixture was stirred for 24 hours at 60-80° C. The reaction mixture was poured into water (50 ml) and extracted with ethyl acetate. The organic layer was washed with brine, dried (sodium sulfate) and evaporated in vacuo. The residue was purified by silica gel (3 g) chromatography eluting with chloroform/methanol (50:1) to give 1-[(R)-4-(6-butoxyindol-1-yl)-1-(tert-butyldimethylsilyloxy)-2-butyl]imidazole-4-carboxamide (66.3 mg, 73.3%).

Workup

  1. stirringthe resulting mixture was stirred for 24 hours at 60-80° C
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried (sodium sulfate)
  5. customevaporated in vacuo
  6. customThe residue was purified by silica gel (3 g) chromatography
  7. washeluting with chloroform/methanol (50:1)

Sources & evidence

ORD record
ord-14f66df9d7c741f9afd68945dbda2682
Source dataset
uspto-grants-2003_07
Patent number
US06596738B1

Reaction notes

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