7-Cyclopentyl-5-ethyl-2-(3-nitrophenyl)imidazo[5,1-f][1,2,4]triazin-4(3H)-one → 2-(3-Aminophenyl)-7-cyclopentyl-5-ethylimidazo[5,1-f][1,2,4]triazin-4(3H)-one

HRID 1791197Notes

Reaction equation

HRID 1791197 reaction equation
[CH:1]1([C:6]2[N:14]3[C:9]([C:10](=[O:24])[NH:11][C:12]([C:15]4[CH:20]=[CH:19][CH:18]=[C:17]([N+:21]([O-])=O)[CH:16]=4)=[N:13]3)=[C:8]([CH2:25][CH3:26])[N:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[H][H]>CO.[Pd]>[NH2:21][C:17]1[CH:16]=[C:15]([C:12]2[NH:11][C:10](=[O:24])[C:9]3=[C:8]([CH2:25][CH3:26])[N:7]=[C:6]([CH:1]4[CH2:5][CH2:4][CH2:3][CH2:2]4)[N:14]3[N:13]=2)[CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 2

HCID 1357525897-Cyclopentyl-5-ethyl-2-(3-nitrophenyl)imidazo[5,1-f][1,2,4]triazin-4(3H)-oneHCID 178418361HCID 178418361, compound2×

Product 1

HCID 1356820222-(3-Aminophenyl)-7-cyclopentyl-5-ethylimidazo[5,1-f][1,2,4]triazin-4(3H)-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

1.8 g (5.1 mmol) 7-cyclopentyl-5-ethyl-2-(3-nitrophenyl)imidazo[5,1-f][1,2,4]triazin-4(3H)-one (Example 21A) are dissolved in 100 ml methanol, and 200 mg palladium (10% on charcoal) are added. The mixture is exposed to an hydrogen atmosphere until no more hydrogen is absorbed. Then the palladium/charcoal is removed by filtration and the filtrate is evaporated to dryness in vacuo. The product is purified by chromatography (flash or column chromatography).

Workup

  1. customis absorbed
  2. customThen the palladium/charcoal is removed by filtration
  3. customthe filtrate is evaporated to dryness in vacuo
  4. customThe product is purified by chromatography (flash or column chromatography)

Sources & evidence

ORD record
ord-4efe20b2dcc24235867d1b924dfb1180
Source dataset
uspto-grants-2006_07
Patent number
US07074790B2

Reaction notes

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