Benzyl isocyanate → HCID 11478533, compound

HRID 1358488Notes

Reaction equation

HRID 1358488 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][N:8]2[CH2:11][CH2:12][C@@H:13]([N:23]2[CH:27]=[C:26]([C:28]([NH2:30])=[O:29])[N:25]=[CH:24]2)[CH2:14][O:15][Si:16]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17])=[CH:4][CH:3]=1.[CH2:31]([N:38]=[C:39]=[O:40])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>C1COCC1>[CH2:31]([NH:38][C:39](=[O:40])[NH:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][N:8]2[CH2:11][CH2:12][C@@H:13]([N:23]2[CH:27]=[C:26]([C:28]([NH2:30])=[O:29])[N:25]=[CH:24]2)[CH2:14][O:15][Si:16]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17])=[CH:4][CH:3]=1)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

4

Reactant 2

HCID 76639Benzyl isocyanateHCID 11224101HCID 11224101, compound

Product 1

HCID 11478533HCID 11478533, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-[(R)-4-(6-aminoindol-1-yl)-1-(tert-butyldimethylsilyloxy)-2-butyl]imidazole-4-carboxamide (100 mg, 0.234 mmol) in THF (5 ml) was added dropwise benzylisocyanate (32 μl, 0.257 mmol). The reaction mixture was stirred at room temperature for 2 hours and the solvent was concentrated in vacuo. The residue was purified by silica gel (4.5 g) column chromatography eluting with chloroform/methanol (30:1) to give 1-[(R)-4-(6-(3-benzylureido)indol-1-yl)-1-(tert-butyldimethylsilyloxy)-2-butyl]imidazole-4-carboxamide (101 mg, 77%) as a pale yellow solid.

Workup

  1. concentrationthe solvent was concentrated in vacuo
  2. customThe residue was purified by silica gel (4.5 g) column chromatography
  3. washeluting with chloroform/methanol (30:1)

Sources & evidence

ORD record
ord-6749f9b995574108acce7bcd8b776fee
Source dataset
uspto-grants-2003_07
Patent number
US06596738B1

Reaction notes

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