Isoamylamine → HCID 178436210, compound

HRID 2174053Notes

Reaction equation

HRID 2174053 reaction equation
[CH3:1][C:2]1[C:3]([CH2:23][C:24]2[NH:28][C:27]3[CH:29]=[CH:30][C:31]([C:33]#[N:34])=[CH:32][C:26]=3[N:25]=2)=[C:4]2[C:8](=[C:9]([CH:11]=[CH2:12])[CH:10]=1)[N:7](S(C1C=CC(C)=CC=1)(=O)=O)[CH:6]=[CH:5]2.[OH-].[K+].C(N)CC(C)C>CCO>[CH3:1][C:2]1[C:3]([CH2:23][C:24]2[NH:28][C:27]3[CH:29]=[CH:30][C:31]([C:33]#[N:34])=[CH:32][C:26]=3[N:25]=2)=[C:4]2[C:8](=[C:9]([CH:11]=[CH2:12])[CH:10]=1)[NH:7][CH:6]=[CH:5]2

Participants

5

Reactant 3

HCID 7894IsoamylamineHCID 14797Potassium HydroxideHCID 178436212HCID 178436212, compound

Product 1

HCID 178436210HCID 178436210, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

2-((5-Methyl-1-tosyl-7-vinyl-1H-indol-4-yl)methyl)-1H-benzo[d]imidazole-5-carbonitrile (23 mg, 0.049 mmol) was dissolved in EtOH (1 mL) and KOH (27.7 mg, 0.493 mmol) and isoamylamine (0.11 mL, 0.986 mmol) were added and the mixture was stirred at 100° C. in the microwave for 30 minutes. The mixture was then stirred at 100° C. in the microwave for another 15 minutes. The reaction was purified directly by flash chromatography (0-100% EtOAc in heptanes) to provide the title compound. MS (ESI+) m/z 313.1 (M+H).

Workup

  1. stirringThe mixture was then stirred at 100° C. in the microwave for another 15 minutes
  2. customThe reaction was purified directly by flash chromatography (0-100% EtOAc in heptanes)

Sources & evidence

ORD record
ord-0a6654a6bc40472cbcbcbc77bd1cb80b
Source dataset
uspto-grants-2015_06
Patent number
US09056874B2

Reaction notes

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