Phosphorus oxychloride → 7-Cyclopentyl-5-ethyl-2-(4-methyl-1-naphthyl)imidazo[5,1-f][1,2,4]triazin-4(3H)-one

HRID 7573Notes

Reaction equation

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

Participants

Reactant 2

HCID 24813Phosphorus oxychloride

HCID 135752584N-{1-[3-(4-methyl-1-naphthyl)-5-oxo-4,5-dihydro-1,2,4-triazin-6-yl]propyl}cyclopentanecarboxamide

Product 1

HCID 1357525307-Cyclopentyl-5-ethyl-2-(4-methyl-1-naphthyl)imidazo[5,1-f][1,2,4]triazin-4(3H)-one

Procedure

In analogy to the procedure for Example 1, 797 mg (2.04 mmol) crude N-{1-[3-(4-methyl-1-naphthyl)-5-oxo-4,5-dihydro-1,2,4-triazin-6-yl]propyl}cyclopentanecarboxamide, 469 mg (3.06 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-2c9227ef32614a76914c4f2107bb68e9
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07087605B2

Reaction notes

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