Phosphorus oxychloride → Benzyl 4-(2-cyclopentyl-5-ethyl-4-oxo-3,4-dihydroimidazo[5,1-f][1,2,4]triazin-7-yl)-1-piperidinecarboxylate

HRID 7588Notes

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][CH2:23][N:22]([C:25]([O:27][CH2:28][C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)=[O:26])[CH2:21][CH2:20]3)=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:1]1([C:6]2[NH:11][C:10](=[O:12])[C:9]3=[C:13]([CH2:14][CH3:15])[N:16]=[C:17]([CH:19]4[CH2:24][CH2:23][N:22]([C:25]([O:27][CH2:28][C:29]5[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=5)=[O:26])[CH2:21][CH2:20]4)[N:8]3[N:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

Reactant 2

HCID 24813Phosphorus oxychloride

HCID 135752573Benzyl 4-({[1-(3-cyclopentyl-5-oxo-4,5-dihydro-1,2,4-triazin-6-yl)propyl]amino} carbonyl)-1-piperidinecarboxylate

Product 1

HCID 135752579Benzyl 4-(2-cyclopentyl-5-ethyl-4-oxo-3,4-dihydroimidazo[5,1-f][1,2,4]triazin-7-yl)-1-piperidinecarboxylate

Procedure

In analogy to the procedure for Example 1, 500 mg (1.07 mmol) crude benzyl 4-({[1-(3-cyclopentyl-5-oxo-4,5-dihydro-1,2,4-triazin-6-yl)propyl]amino}carbonyl)-1-piperidinecarboxylate, 248 mg (1.7 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

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

Sources & evidence

ORD record: ord-ce06e1276c0a4ff28619deb78bf9e8ac
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07087605B2

Reaction notes

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