Diethyl Ether → HCID 86588795, compound

HRID 1072017Notes

Reaction equation

HRID 1072017 reaction equation
[N:1]1([CH2:10][C:11]2[N:15]([CH2:16][CH2:17][C:18]([NH:20]O)=[NH:19])[C:14]3[CH:22]=[CH:23][CH:24]=[CH:25][C:13]=3[N:12]=2)[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[N:2]1.[C:26]([O:29]C(=O)C)(=[O:28])[CH3:27].C(OCC)C>C(O)(=O)C.[Pd]>[C:26]([OH:29])(=[O:28])[CH3:27].[C:26]([OH:29])(=[O:28])[CH3:27].[N:1]1([CH2:10][C:11]2[N:15]([CH2:16][CH2:17][C:18]([NH2:20])=[NH:19])[C:14]3[CH:22]=[CH:23][CH:24]=[CH:25][C:13]=3[N:12]=2)[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[N:2]1

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 7918Acetic AnhydrideHCID 178511104HCID 178511104, compound

Product 1

HCID 86588795HCID 86588795, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

N-[3-(2-Benzotriazol-1-ylmethyl-benzimidazol-1-yl)-1-imino-propyl)-hydroxyamine (57 mg, 0.17 mmol) was dissolved in acetic acid (1 mL). Acetic anhydride was added and the solution was stirred at room temperature for 5-10 minutes. The solution was then added to 10% Pd/C (15 mg) in a Parr reaction vessel. The mixture was agitated under H2 (at 55 psi) for 4 hours. The catalyst was removed by filtration. Evaporation of the filtrate gave a yellow gum which was azeotroped with hexane several times. Trituration with diethyl ether gave 64 mg (64% yield) of the title compound as a tan solid.

Workup

  1. stirringThe mixture was agitated under H2 (at 55 psi) for 4 hours
  2. customThe catalyst was removed by filtration
  3. customEvaporation of the filtrate
  4. customgave a yellow gum which
  5. customwas azeotroped with hexane several times

Sources & evidence

ORD record
ord-e34ad697d9984957bbed264f08813fff
Source dataset
uspto-grants-2005_06
Patent number
US06908936B2

Reaction notes

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