2-Amino-1-(thiophen-2-yl)ethan-1-one hydrochloride → 3-Methyl-4-oxo-N-(2-oxo-2-(thiophen-2-yl)ethyl)-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazine-8-carboximidamide hydroiodide

HRID 570943Notes

Reaction equation

HRID 570943 reaction equation
[IH:1].[CH3:2][N:3]1[C:8](=[O:9])[N:7]2[CH:10]=[N:11][C:12]([C:13](SC)=[NH:14])=[C:6]2[N:5]=[N:4]1.Cl.[NH2:18][CH2:19][C:20]([C:22]1[S:23][CH:24]=[CH:25][CH:26]=1)=[O:21]>>[IH:1].[CH3:2][N:3]1[C:8](=[O:9])[N:7]2[CH:10]=[N:11][C:12]([C:13](=[NH:14])[NH:18][CH2:19][C:20](=[O:21])[C:22]3[S:23][CH:24]=[CH:25][CH:26]=3)=[C:6]2[N:5]=[N:4]1

Participants

3

Reactant 2

HCID 126098332-Amino-1-(thiophen-2-yl)ethan-1-one hydrochlorideHCID 66831606Methyl 3-methyl-4-oxo-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazine-8-carbimidothioate hydroiodide

Product 1

HCID 1784819793-Methyl-4-oxo-N-(2-oxo-2-(thiophen-2-yl)ethyl)-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazine-8-carboximidamide hydroiodideYield 66%

Procedure

Using the general procedure, the title compound was synthesized from methyl 3-methyl-4-oxo-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazine-8-carbimidothioate hydroiodide and 2-amino-1-(thiophen-2-yl)ethanone hydrochloride, using a reaction time of 16 hours for the amidine formation. Yield 66%. δH (DMSO-d6): 9.76-9.73 (1H, m), 9.69 (1H, s), 9.49 (1H, bs), 9.22 (1H, s), 8.16 (1H, dd, J=4.9, 1.1), 8.12 (1H, dd, J=3.8, 1.1), 7.37 (1H, dd, J=4.9, 3.8), 5.17 (2H, d, J=6.3), 4.06 (3H, s).

Workup

  1. customa reaction time of 16 hours

Sources & evidence

ORD record
ord-65b88a21b0af49e4a58c3ce7fcb94036
Source dataset
uspto-grants-2015_05
Patent number
US09024018B2

Reaction notes

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