Lawesson's reagent → 1,1-Dimethylethyl 3-(aminocarbonothioyl)-5,6-dihydro[1,2,4]triazolo[4,3-a]pyrazine-7(8H)-carboxylate

HRID 1889041Notes

Reaction equation

[NH2:1][C:2]([C:4]1[N:8]2[CH2:9][CH2:10][N:11]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:12][C:7]2=[N:6][N:5]=1)=O.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:29])=CC=1>C1C=CC=CC=1>[NH2:1][C:2]([C:4]1[N:8]2[CH2:9][CH2:10][N:11]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:12][C:7]2=[N:6][N:5]=1)=[S:29]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 1,1-dimethylethyl 3-(aminocarbonyl)-5,6-dihydro[1,2,4]triazolo[4,3-a]pyrazine-7(8H)-carboxylate (I111) (0.2 g, 0.748 mmol) and Lawesson's reagent (0.151 g, 0.374 mmol) in benzene (7.48 ml) was heated at 80° C. for 2 h, left to stand over the weekend at RT and then heated for a further 6 h at 80° C. The mixture was cooled, concentrated and then chromatographed (0-5% MeOH in DCM) to give the desired product as a yellow solid in 99 mg.

Workup

waitleft
customto stand over the weekend at RT
temperatureheated for a further 6 h at 80° C
temperatureThe mixture was cooled
concentrationconcentrated
customchromatographed (0-5% MeOH in DCM)

Sources & evidence

ORD record: ord-6e0d081da46342a590fb6459e773dce3
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08501946B2

Reaction notes

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