Phosphorus oxychloride → 2-tert-Butyl-7-cyclopentyl-5-ethylimidazo[5,1-f][1,2,4]triazin-4(3H)-one

HRID 7569Notes

Reaction equation

[C:1]([C:5]1[NH:10][C:9](=[O:11])[C:8]([CH:12]([NH:15][C:16]([CH:18]2[CH2:22][CH2:21][CH2:20][CH2:19]2)=O)[CH2:13][CH3:14])=[N:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2].P(Cl)(Cl)(Cl)=O>>[C:1]([C:5]1[NH:10][C:9](=[O:11])[C:8]2=[C:12]([CH2:13][CH3:14])[N:15]=[C:16]([CH:18]3[CH2:22][CH2:21][CH2:20][CH2:19]3)[N:7]2[N:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

Reactant 2

HCID 24813Phosphorus oxychloride

HCID 135752563N-[1-(3-tert-butyl-5-oxo-4,5-dihydro-1,2,4-triazin-6-yl)propyl]cyclopentanecarboxamide

Product 1

HCID 1357525462-tert-Butyl-7-cyclopentyl-5-ethylimidazo[5,1-f][1,2,4]triazin-4(3H)-one

Procedure

In analogy to the procedure for Example 1, 150 mg (0.50 mmol) crude N-[1-(3-tert-butyl-5-oxo-4,5-dihydro-1,2,4-triazin-6-yl)propyl]cyclopentanecarboxamide, 80 mg (0.50 mmol) phosphoric trichloride are stirred at reflux for 3 hours, proportionate amounts of the solvents are used.

Workup

temperatureat reflux for 3 hours

Sources & evidence

ORD record: ord-c462ab3399b44288913d58477018dab0
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07087605B2

Reaction notes

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