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

HRID 7574Notes

Reaction equation

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

Participants

Reactant 2

HCID 24813Phosphorus oxychloride

HCID 135752615N-[1-(3-Cyclopentyl-5-oxo-4,5-dihydro-1,2,4-triazin-6-yl)propyl]-2-methylcyclopropanecarboxamide

Product 1

HCID 1357525852-Cyclopentyl-5-ethyl-7-(2-methylcyclopropyl)imidazo[5,1-f][1,2,4]triazin-4(3H)-one

Procedure

In analogy to the procedure for Example 1, 200 mg (0.66 mmol) crude N-[1-(3-cyclopentyl-5-oxo-4,5-dihydro-1,2,4-triazin-6-yl)propyl]-2-methylcyclopropanecarboxamide, 165 mg (1.1 mmol) phosphoric trichloride are stirred at reflux for 4 hours, proportionate amounts of the solvents are used. The isomers are purified by chromatography (preparative HPLC).

Workup

temperatureat reflux for 4 hours
customThe isomers are purified by chromatography (preparative HPLC)

Sources & evidence

ORD record: ord-c6d0c18f8ded43c484f88d5c0477190e
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07087605B2

Reaction notes

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