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

HRID 7570Notes

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

Participants

Reactant 2

HCID 24813Phosphorus oxychloride

HCID 135752666N-[1-(3-cyclopentyl-5-oxo-4,5-dihydro-1,2,4-triazin-6-yl)propyl]cyclobutanecarboxamide

Product 1

HCID 1357525577-Cyclobutyl-2-cyclopentyl-5-ethylimidazo[5,1-f][1,2,4]triazin-4(3H)-one

Procedure

In analogy to the procedure for Example 1, 270 mg (0.90 mmol) crude N-[1-(3-cyclopentyl-5-oxo-4,5-dihydro-1,2,4-triazin-6-yl)propyl]cyclobutanecarboxamide, 140 mg (0.90 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-cf45ab27f34c4f82a0dd0b3275ab9fd7
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07087605B2

Reaction notes

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