1-Propanol → HCID 67071817, compound

HRID 2094204Notes

Reaction equation

HRID 2094204 reaction equation
[CH2:1](O)[CH2:2][CH3:3].N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O.[NH2:23][C:24]([NH:26][C:27]1[NH:28][C:29]2[C:34]([C:35]=1[C:36]([NH2:38])=[O:37])=[CH:33][CH:32]=[C:31]([OH:39])[CH:30]=2)=[O:25]>O1CCCC1>[NH2:23][C:24]([NH:26][C:27]1[NH:28][C:29]2[C:34]([C:35]=1[C:36]([NH2:38])=[O:37])=[CH:33][CH:32]=[C:31]([O:39][CH2:1][CH2:2][CH3:3])[CH:30]=2)=[O:25]

Participants

5

Reactant 3

HCID 10311-PropanolHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 44609572HCID 44609572, compound

Product 1

HCID 67071817HCID 67071817, compoundYield 13%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under ice-cooling, 1-propanol (60 μL, 0.80 mmol), n-tributylphosphine (100 μL, 0.40 mmol) and 1,1′-(azodicarbonyl)dipiperidine (98 mg, 0.39 mmol) were added to a suspension of 2-aminocarbonylamino-6-hydroxyindole-3-carboxamide (Compound No.2-1, 47 mg, 0.20 mmol) in anhydrous tetrahydrofuran (2 mL) and stirred for 2.5 hours. Moreover the whole was stirred overnight at room temperature, and stirred at 50° C. for 7 hours. The reaction solution was purified by silica gel column chromatography to give the title compound (7 mg) as a green solid (13%).

Workup

  1. temperatureUnder ice-cooling
  2. stirringMoreover the whole was stirred overnight at room temperature
  3. stirringstirred at 50° C. for 7 hours
  4. customThe reaction solution was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-1f4df8228b7246fa8649dd8944274aa0
Source dataset
uspto-grants-2013_05
Patent number
US08445529B2

Reaction notes

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