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

HRID 1791186Notes

Reaction equation

[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2[NH:15][C:14](=[O:16])[C:13]([CH:17]([NH:20][C:21]([CH:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)=O)[CH2:18][CH3:19])=[N:12][N:11]=2)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].O=P(Cl)(Cl)Cl.C([O-])(O)=O.[Na+]>ClC(Cl)C>[CH:23]1([C:21]2[N:12]3[C:13]([C:14](=[O:16])[NH:15][C:10]([C:6]4[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=4)=[N:11]3)=[C:17]([CH2:18][CH3:19])[N:20]=2)[CH2:27][CH2:26][CH2:25][CH2:24]1

Participants

Conditions

Temperature: 0 °C

Procedure

3.5 g (9.4 mmol) N-{1-[3-(3-nitrophenyl)-5-oxo-4,5-dihydro-1,2,4-triazin-6-yl]propyl}-cyclopentanecarboxamide (Example 19A) are suspended in 60 ml dichloroethane, and 1.45 g (9.4 mmol) phosphoroxychloride are added. The mixture is stirred at reflux for 3 hour. After cooling down to 0° C., 10 ml saturated NaHCO3 (aq) is added dropwise. The mixture is stirred for about 20 min at room temperature and then evaporated to dryness in vacuo. The product is purified by chromatography (flash or column chromatography).

Workup

temperatureat reflux for 3 hour
stirringThe mixture is stirred for about 20 min at room temperature
customevaporated to dryness in vacuo
customThe product is purified by chromatography (flash or column chromatography)

Sources & evidence

ORD record: ord-cb90fbfc22ad4b189a6629d9ec2fd186
Source dataset: uspto-grants-2006_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07074790B2

Reaction notes

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