Ethanone, 2-amino-1-phenyl-, hydrochloride (1:1) → HCID 178456701, compound

HRID 570944Notes

Reaction equation

HRID 570944 reaction equation
[IH:1].[O:2]=[C:3]1[N:8]([CH2:9][C:10]#[CH:11])[N:7]=[N:6][C:5]2=[C:12]([C:15](SC)=[NH:16])[N:13]=[CH:14][N:4]12.Cl.[NH2:20][CH2:21][C:22]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:23]>>[IH:1].[O:2]=[C:3]1[N:8]([CH2:9][C:10]#[CH:11])[N:7]=[N:6][C:5]2=[C:12]([C:15](=[NH:16])[NH:20][CH2:21][C:22](=[O:23])[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[N:13]=[CH:14][N:4]12

Participants

3

Reactant 2

HCID 2723597Ethanone, 2-amino-1-phenyl-, hydrochloride (1:1)HCID 86663789Methyl 4-oxo-3-(prop-2-ynyl)-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazine-8-carbimidothioate hydroiodide

Product 1

HCID 178456701HCID 178456701, compoundYield 29%

Procedure

Using the general procedure, the title compound was synthesized from methyl 4-oxo-3-(prop-2-ynyl)-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazine-8-carbimidothioate hydroiodide and aminoacetophenone hydrochloride, using a reaction time of 5 hours and 30 minutes for the amidine formation. Yield 29%. δH (DMSO-d6): 9.74 (2H, m), 9.54 (1H, bs), 9.25 (1H, s), 8.07-8.05 (2H, m), 7.78-7.73 (1H, m), 7.65-7.61 (2H, m), 5.27-5.24 (4H, m), 3.62 (1H, t, J=2.5).

Workup

  1. customa reaction time of 5 hours and 30 minutes

Sources & evidence

ORD record
ord-81d4ea4c63ec4a219ae3e6daa569c4e9
Source dataset
uspto-grants-2015_05
Patent number
US09024018B2

Reaction notes

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