Cyclohexane → 2-(5-Amino-2-ethoxyphenyl)-5-methyl-7-(2-ethylheptyl)-3H-imidazo[5,1-f][1,2,4]-triazin-4-one

HRID 11268Notes

Reaction equation

HRID 11268 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-])=O)=[CH:6][C:5]=1[C:13]1[NH:18][C:17](=[O:19])[C:16]2=[C:20]([CH3:32])[N:21]=[C:22]([CH2:23][CH:24]([CH2:30][CH3:31])[CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[N:15]2[N:14]=1)[CH3:2].C1CCCCC1.C(OCC)(=O)C>C(O)C.[Pd]>[NH2:10][C:7]1[CH:8]=[CH:9][C:4]([O:3][CH2:1][CH3:2])=[C:5]([C:13]2[NH:18][C:17](=[O:19])[C:16]3=[C:20]([CH3:32])[N:21]=[C:22]([CH2:23][CH:24]([CH2:30][CH3:31])[CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[N:15]3[N:14]=2)[CH:6]=1

Participants

6

Reactant 3

HCID 8078CyclohexaneHCID 8857Ethyl AcetateHCID 1363363272-(2-Ethoxy-5-nitrophenyl)-5-methyl-7-(2-ethylheptyl)-3H-imidazo[5,1-f][1,2,4]-triazin-4-one

Product 1

HCID 1363363262-(5-Amino-2-ethoxyphenyl)-5-methyl-7-(2-ethylheptyl)-3H-imidazo[5,1-f][1,2,4]-triazin-4-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Analogously to the procedure of example 42A, 1.95 g (4.42 mmol) of the compound from example 49A are hydrogenated in 120 g of ethanol using 200 mg of 10% Pd/C. Chromatography on 400 ml of silica gel using cyclohexane and ethyl acetate in a gradient system from 90:10 to 40:60 gives 1.26 g (69.4% of theory).

Workup

  1. customgives 1.26 g (69.4% of theory)

Sources & evidence

ORD record
ord-beb9284104874dccbc49023925c5f0f0
Source dataset
uspto-grants-2006_08
Patent number
US07098207B2

Reaction notes

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