Phosphorus oxychloride → 2-tert-Butyl-7-(4-tert-butylcyclohexyl)-5-ethylimidazo[5,1-f][1,2,4]triazin-4(3H)-one
Reaction equation
[C:1]([CH:5]1[CH2:10][CH2:9][CH:8]([C:11]([NH:13][CH:14]([C:17]2[C:18](=[O:27])[NH:19][C:20]([C:23]([CH3:26])([CH3:25])[CH3:24])=[N:21][N:22]=2)[CH2:15][CH3:16])=O)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].P(Cl)(Cl)(Cl)=O>>[C:23]([C:20]1[NH:19][C:18](=[O:27])[C:17]2=[C:14]([CH2:15][CH3:16])[N:13]=[C:11]([CH:8]3[CH2:9][CH2:10][CH:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH2:6][CH2:7]3)[N:22]2[N:21]=1)([CH3:26])([CH3:25])[CH3:24]Participants
3
Procedure
In analogy to the procedure for Example 1, 377 mg (1.00 mmol) crude 4-tert-butyl-N-[1-(3-tert-butyl-5-oxo-4,5-dihydro-1,2,4-triazin-6-yl)propyl]cyclohexanecarboxamide, 184 mg (1.20 mmol) phosphoric trichloride are stirred at reflux for 3 hours, proportionate amounts of the solvents are used. The resulting mixture is separated into the pure cis- and trans-isomers via silica gel chromatography with eluent cyclohexane/ethylacetate 10/1, 5/1.
Workup
- temperatureat reflux for 3 hours
- customThe resulting mixture is separated into the pure cis- and trans-isomers via silica gel chromatography with eluent cyclohexane/ethylacetate 10/1, 5/1
Sources & evidence
- ORD record
- ord-f4ded32ca50a40ae99b1bb356320248f
- Source dataset
- uspto-grants-2006_10
- Patent number
- US07115602B2
Reaction notes
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