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

HRID 7577Notes

Reaction equation

HRID 7577 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[CH2:24][CH:23]4[CH2:25][CH:20]3[CH:21]=[CH:22]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>>[CH:20]12[CH2:25][CH:23]([CH:22]=[CH:21]1)[CH2:24][CH:19]2[C:17]1[N:8]2[C:9]([C:10](=[O:12])[NH:11][C:6]([CH:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)=[N:7]2)=[C:13]([CH2:14][CH3:15])[N:16]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 135752647N-[1-(3-Cyclopentyl-5-oxo-4,5-dihydro-1,2,4-triazin-6-yl)propyl]bicyclo[2.2.1]hept-5-ene-2-carboxamide

Product 1

HCID 1357526087-Bicyclo[2.2.1]hept-5-en-2-yl-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 (0.58 mmol) crude N-[1-(3-cyclopentyl-5-oxo-4,5-dihydro-1,2,4-triazin-6-yl)propyl]bicyclo[2.2.1]hept-5-ene-2-carboxamide, 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

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

Sources & evidence

ORD record
ord-f94205c2ea4a4c8380418be35042d758
Source dataset
uspto-grants-2006_08
Patent number
US07087605B2

Reaction notes

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