[1-(2-azidoethyl)-1H-benzimidazol-5-yl]-(3-hydroxy-8-azabicyclo[3.2.1]oct-8-yl)methanone → [1-(2-aminoethyl)-1H-benzimidazol-5-yl]-(3-hydroxy-8-aza-bicyclo[3.2.1]oct-8-yl)methanone

HRID 555295Notes

Reaction equation

HRID 555295 reaction equation
[N:1]([CH2:4][CH2:5][N:6]1[C:10]2[CH:11]=[CH:12][C:13]([C:15]([N:17]3[CH:22]4[CH2:23][CH2:24][CH:18]3[CH2:19][CH:20]([OH:25])[CH2:21]4)=[O:16])=[CH:14][C:9]=2[N:8]=[CH:7]1)=[N+]=[N-]>CO.[Pd]>[NH2:1][CH2:4][CH2:5][N:6]1[C:10]2[CH:11]=[CH:12][C:13]([C:15]([N:17]3[CH:18]4[CH2:24][CH2:23][CH:22]3[CH2:21][CH:20]([OH:25])[CH2:19]4)=[O:16])=[CH:14][C:9]=2[N:8]=[CH:7]1

Participants

4

Reactant 1

HCID 86630059[1-(2-azidoethyl)-1H-benzimidazol-5-yl]-(3-hydroxy-8-azabicyclo[3.2.1]oct-8-yl)methanone

Product 1

HCID 66987621[1-(2-aminoethyl)-1H-benzimidazol-5-yl]-(3-hydroxy-8-aza-bicyclo[3.2.1]oct-8-yl)methanoneYield 86%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of [1-(2-azidoethyl)-1H-benzimidazol-5-yl]-(3-hydroxy-8-aza-bicyclo[3.2.1]oct-8-yl)methanone (1.1 g, 0.0035 mol) in methanol (15 mL) was added 10% Pd/C (0.17 g) and the mixture hydrogenated at 3 kg pressure for 1 h. The catalyst was filtered over celite and the filtrate was concentrated to give [1-(2-aminoethyl)-1H-benzimidazol-5-yl]-(3-hydroxy-8-aza-bicyclo[3.2.1]oct-8-yl)methanone (0.87 g, 86%). MS-ES I m/z 315 (M+1).

Workup

  1. filtrationThe catalyst was filtered over celite
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-79e3eb9217fb49bb9cc60ae6660d52f1
Source dataset
uspto-grants-2011_11
Patent number
US08053431B2

Reaction notes

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