2-((1-cyclopropyl-2-oxo-1H-imidazo[4,5-c]pyridin-3(2H)-yl)methyl)-3-isopentyl-3H-imidazo[4,5-b]pyridine-6-carbonitrile → 3-((6-(aminomethyl)-3-isopentyl-3H-imidazo[4,5-b]pyridine-2-yl)methyl)-1-cyclopropyl-1H-imidazo[4,5-c]pyridin-2(3H)-one

HRID 632860Notes

Reaction equation

HRID 632860 reaction equation
[CH:1]1([N:4]2[C:12]3[CH:11]=[CH:10][N:9]=[CH:8][C:7]=3[N:6]([CH2:13][C:14]3[N:24]([CH2:25][CH2:26][CH:27]([CH3:29])[CH3:28])[C:17]4=[N:18][CH:19]=[C:20]([C:22]#[N:23])[CH:21]=[C:16]4[N:15]=3)[C:5]2=[O:30])[CH2:3][CH2:2]1>CO.N.[Ni]>[NH2:23][CH2:22][C:20]1[CH:21]=[C:16]2[N:15]=[C:14]([CH2:13][N:6]3[C:7]4[CH:8]=[N:9][CH:10]=[CH:11][C:12]=4[N:4]([CH:1]4[CH2:2][CH2:3]4)[C:5]3=[O:30])[N:24]([CH2:25][CH2:26][CH:27]([CH3:29])[CH3:28])[C:17]2=[N:18][CH:19]=1

Participants

4

Reactant 1

HCID 573788812-((1-cyclopropyl-2-oxo-1H-imidazo[4,5-c]pyridin-3(2H)-yl)methyl)-3-isopentyl-3H-imidazo[4,5-b]pyridine-6-carbonitrile

Product 1

HCID 679918153-((6-(aminomethyl)-3-isopentyl-3H-imidazo[4,5-b]pyridine-2-yl)methyl)-1-cyclopropyl-1H-imidazo[4,5-c]pyridin-2(3H)-one

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 21705897Ammonia methanolSolvent

Procedure

Compound 27 (125 mg, 0.31 mmol) in methanol/NH3 (100 mL) was hydrogenated at 20° C. with Raney Nickel (50 mg) as a catalyst overnight. After uptake of H2 (2 eq), the catalyst was filtered off and the filtrate was evaporated. The residue was purified by column chromatography using dichloromethane/MeOH/NH3. The title compound 17 was isolated as a white solid (25.5 mg, 20%). m/z=406 (M+H)+.

Workup

  1. filtrationAfter uptake of H2 (2 eq), the catalyst was filtered off
  2. customthe filtrate was evaporated
  3. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-bcce6d952d124d5e9c9c6ef6c332bc98
Source dataset
uspto-grants-2016_04
Patent number
US09321767B2

Reaction notes

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