Nitric Acid → 2-(2-Ethoxy-5-nitrophenyl)-5-methyl-7-cyclopentyl-3H-imidazo[5,1-f][1,2,4]-triazin-4-one

HRID 11264Notes

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

Using an ice-acetone bath, 48.6 ml of trifluoroacetic acid (TFA and 12.1 ml of 70% strength nitric acid are cooled to −10° C., 3.0 g (8.86 mmol) of the compound from example 25A, dissolved in 7 ml of TFA are added dropwise, and the mixture is stirred at 0° C. for 20 hours. The reaction solution is stirred into 400 ml of ice-water and 200 ml of dichloromethane and neutralized using about 200 ml of saturated sodium bicarbonate solution. The aqueous phase is separated off and extracted 3 times with dichloromethane, and the combined organic phases are dried and concentrated. The residue is chromatographed on silica gel using toluene with added ethyl acetate in a gradient from 11 to 60%.

Workup

additionare added dropwise
customThe aqueous phase is separated off
extractionextracted 3 times with dichloromethane
customthe combined organic phases are dried
concentrationconcentrated
customThe residue is chromatographed on silica gel

Sources & evidence

ORD record: ord-ebb0166aad5942ed9b0e31b364855402
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07098207B2

Reaction notes

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