HCID 6481622, compound → HCID 5272002, compound

HRID 1072013Notes

Reaction equation

HRID 1072013 reaction equation
[N:1]([CH2:4][CH2:5][N:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[N:8]=[C:7]1[CH2:15][N:16]1[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[N:18]=[N:17]1)=[N+]=[N-]>[Pd].CO>[N:16]1([CH2:15][C:7]2[N:6]([CH2:5][CH2:4][NH2:1])[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=3[N:8]=2)[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[N:18]=[N:17]1

Participants

4

Reactant 1

HCID 6481622HCID 6481622, compound

Product 1

HCID 5272002HCID 5272002, compoundYield 100.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 1-[1-(2-azido-ethyl)-1-H-benzimidazol-2-ylmethyl)-1H-benzotriazole (25 mg, 0.078 mmol) and 10% palladium on carbon in 1 mL of methanol was agitated under hydrogen at 55 psi for 5 hours. The reaction mixture was filtered through a pad of Celite and then through a Millipore membrane filter rinsing with methanol. The filtrate was stripped of solvent and dried under vacuum to give the amine (23 mg, quantitative yield) as a white solid.

Workup

  1. filtrationThe reaction mixture was filtered through a pad of Celite
  2. filtrationthrough a Millipore membrane filter
  3. washrinsing with methanol
  4. customdried under vacuum

Sources & evidence

ORD record
ord-d7c6f2797a4640089d3998ccc0d2c1ca
Source dataset
uspto-grants-2005_06
Patent number
US06908936B2

Reaction notes

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