Phosphorus oxychloride → 7-(Bicyclo[2.2.1]hept-2-ylmethyl)-2-cyclopentyl-5-ethylimidazo[5,1-f][1,2,4]triazin-4(3H)-one

HRID 7578Notes

Reaction equation

HRID 7578 reaction equation
[CH:1]12[CH2:7][CH:4]([CH2:5][CH2:6]1)[CH2:3][CH:2]2[CH2:8][C:9]([NH:11][CH:12]([C:15]1[C:16](=[O:26])[NH:17][C:18]([CH:21]2[CH2:25][CH2:24][CH2:23][CH2:22]2)=[N:19][N:20]=1)[CH2:13][CH3:14])=O.P(Cl)(Cl)(Cl)=O>>[CH:1]12[CH2:7][CH:4]([CH2:5][CH2:6]1)[CH2:3][CH:2]2[CH2:8][C:9]1[N:20]2[C:15]([C:16](=[O:26])[NH:17][C:18]([CH:21]3[CH2:25][CH2:24][CH2:23][CH2:22]3)=[N:19]2)=[C:12]([CH2:13][CH3:14])[N:11]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 1357525282-Bicyclo[2.2.1]hept-2-yl-N-[1-(3-cyclopentyl-5-oxo-4,5-dihydro-1,2,4-triazin-6-yl)propyl]acetamide

Product 1

HCID 1357526927-(Bicyclo[2.2.1]hept-2-ylmethyl)-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 (0.56 mmol) crude 2-bicyclo[2.2.1]hept-2-yl-N-[1-(3-cyclopentyl-5-oxo-4,5-dihydro-1,2,4-triazin-6-yl)-propyl]acetamide, 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-10735c9d20bb40cd8277b789c9878804
Source dataset
uspto-grants-2006_08
Patent number
US07087605B2

Reaction notes

Loading…