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

HRID 7583Notes

Reaction equation

HRID 7583 reaction equation
[CH:1]1([C:6]2[NH:11][C:10](=[O:12])[C:9]([CH:13]([NH:16][C:17]([C:19]34[CH2:28][CH:23]5[CH2:24][CH:25]([CH2:27][CH:21]([CH2:22]5)[CH2:20]3)[CH2:26]4)=O)[CH2:14][CH3:15])=[N:8][N:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.P(Cl)(Cl)(Cl)=O>>[C:19]12([C:17]3[N:8]4[C:9]([C:10](=[O:12])[NH:11][C:6]([CH:1]5[CH2:5][CH2:4][CH2:3][CH2:2]5)=[N:7]4)=[C:13]([CH2:14][CH3:15])[N:16]=3)[CH2:20][CH:21]3[CH2:22][CH:23]([CH2:24][CH:25]([CH2:27]3)[CH2:26]1)[CH2:28]2

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 135752600N-[1-(3-Cyclopentyl-5-oxo-4,5-dihydro-1,2,4-triazin-6-yl)propyl]-1-adamantanecarboxamide

Product 1

HCID 1357526017-(1-Adamantyl)-2-cyclopentyl-5-ethylimidazo[5,1-f][1,2,4]triazin-4(3H)-one

Procedure

In analogy to the procedure for Example 1, 200 mg (0.52 mmol) crude N-[1-(3-cyclopentyl-5-oxo-4,5-dihydro-1,2,4-triazin-6-yl)propyl]-1-adamantanecarboxamide, 165 mg (1.1 mmol) phosphoric trichloride are stirred at reflux for 4 hours, proportionate amounts of the solvents are used. The product is purified by chromatography (preparative HPLC).

Workup

  1. temperatureat reflux for 4 hours
  2. customThe product is purified by chromatography (preparative HPLC)

Sources & evidence

ORD record
ord-06d291966cce4ad0bd1551ebc0ed2ff5
Source dataset
uspto-grants-2006_08
Patent number
US07087605B2

Reaction notes

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