5-Nitro-2-propoxyphenyl-5-methyl-7-cyclopentyl-3H-imidazo[5,1-f][1,2,4]-triazin-4-one → 2-(5-Amino-2-propoxyphenyl)-5-methyl-7-cyclopentyl-3H-imidazo[5,1-f][1,2,4]-triazin-4-one

HRID 1814831Notes

Reaction equation

HRID 1814831 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([O:26][CH2:27][CH2:28][CH3:29])=[C:8]([C:10]2[NH:15][C:14](=[O:16])[C:13]3=[C:17]([CH3:25])[N:18]=[C:19]([CH:20]4[CH2:24][CH2:23][CH2:22][CH2:21]4)[N:12]3[N:11]=2)[CH:9]=1)([O-])=O>O1CCCC1.C(O)C.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([O:26][CH2:27][CH2:28][CH3:29])=[C:8]([C:10]2[NH:15][C:14](=[O:16])[C:13]3=[C:17]([CH3:25])[N:18]=[C:19]([CH:20]4[CH2:24][CH2:23][CH2:22][CH2:21]4)[N:12]3[N:11]=2)[CH:9]=1

Participants

4

Reactant 1

HCID 1356049635-Nitro-2-propoxyphenyl-5-methyl-7-cyclopentyl-3H-imidazo[5,1-f][1,2,4]-triazin-4-one

Product 1

HCID 1356049252-(5-Amino-2-propoxyphenyl)-5-methyl-7-cyclopentyl-3H-imidazo[5,1-f][1,2,4]-triazin-4-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

Analogously to the procedure of example 42A 5.13 g (12.96 mmol) of the compound from example 43A are hydrogenated in tetrahydrofuran/ethanol (1:1) using 1.11 g of 10% Pd/C. The product is purified by silica gel chromatography using toluene and ethyl acetate as solvent gradient.

Workup

  1. customThe product is purified by silica gel chromatography

Sources & evidence

ORD record
ord-77b1c032bd4b456f9e89305981c59c09
Source dataset
uspto-grants-2005_04
Patent number
US06878708B2

Reaction notes

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