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

HRID 7568Notes

Reaction equation

[CH:1]1([C:4]2[NH:9][C:8](=[O:10])[C:7]([CH:11]([NH:14][C:15]([CH:17]3[CH2:21][CH2:20][CH2:19][CH2:18]3)=O)[CH2:12][CH3:13])=[N:6][N:5]=2)[CH2:3][CH2:2]1.P(Cl)(Cl)(Cl)=O>>[CH:17]1([C:15]2[N:6]3[C:7]([C:8](=[O:10])[NH:9][C:4]([CH:1]4[CH2:3][CH2:2]4)=[N:5]3)=[C:11]([CH2:12][CH3:13])[N:14]=2)[CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

Reactant 2

HCID 24813Phosphorus oxychloride

HCID 135752607N-[1-(3-cyclopropyl-5-oxo-4,5-dihydro-1,2,4-triazin-6-yl)propyl]cyclopentanecarboxamide

Product 1

HCID 1357525947-Cyclopentyl-2-cyclopropyl-5-ethylimidazo[5,1-f][1,2,4]triazin-4(3H)-one

Procedure

In analogy to the procedure for Example 1, 370 mg (1.28 mmol) crude N-[1-(3-cyclopropyl-5-oxo-4,5-dihydro-1,2,4-triazin-6-yl)propyl]cyclopentanecarboxamide, 200 mg (1.28 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-644fc957d9a84e2ba138f5e61c9a83ef
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07087605B2

Reaction notes

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