Adamantane carboxylic acid [2-(4-nitro-phenyl)-3H-imidazo[4,5-c]pyridine-6-yl]-amide → Adamantane carboxylic acid [2-(4-amino-phenyl)-3H-imidazo[4,5-c]pyridine-6-yl]-amide

HRID 854086Notes

Reaction equation

HRID 854086 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[NH:31][C:13]3[CH:14]=[N:15][C:16]([NH:18][C:19]([C:21]45[CH2:30][CH:25]6[CH2:26][CH:27]([CH2:29][CH:23]([CH2:24]6)[CH2:22]4)[CH2:28]5)=[O:20])=[CH:17][C:12]=3[N:11]=2)=[CH:6][CH:5]=1)([O-])=O>[Ni].CCO>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[NH:31][C:13]3[CH:14]=[N:15][C:16]([NH:18][C:19]([C:21]45[CH2:22][CH:23]6[CH2:29][CH:27]([CH2:26][CH:25]([CH2:24]6)[CH2:30]4)[CH2:28]5)=[O:20])=[CH:17][C:12]=3[N:11]=2)=[CH:8][CH:9]=1

Participants

4

Reactant 1

HCID 58932930Adamantane carboxylic acid [2-(4-nitro-phenyl)-3H-imidazo[4,5-c]pyridine-6-yl]-amide

Product 1

HCID 58932924Adamantane carboxylic acid [2-(4-amino-phenyl)-3H-imidazo[4,5-c]pyridine-6-yl]-amideYield 107.5%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A solution of 13 (0.200 g, 0.48 mmol) and Raney Nickel (0.200 ml) in EtOH (10 ml) was stirred under H2 atmosphere at 80° C. for 90 min. TLC showed no starting material. The product was freed from catalyst by filtering through a celite pad and evaporated to dryness to afford the amine 14 (0.200 g, 100%) used for the next step.

Workup

  1. filtrationby filtering through a celite pad
  2. customevaporated to dryness

Sources & evidence

ORD record
ord-f2b3507383784ab7b0076bdb988da819
Source dataset
uspto-grants-2007_08
Patent number
US07256287B2

Reaction notes

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