Hydrochloric Acid → 3-Amino-6-(1-isopropyl-6-oxo-1,6-dihydro-3-pyridazinyl)-5-phenyl-2-pyrazinecarbothioamide

HRID 915031Notes

Reaction equation

[NH2:1][C:2]1[C:3]([C:24]#[N:25])=[N:4][C:5]([C:14]2[CH:19]=[CH:18][C:17](=[O:20])[N:16]([CH:21]([CH3:23])[CH3:22])[N:15]=2)=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:7]=1.C(N)(=[S:28])C.Cl.O1CCOCC1>CN(C=O)C.O>[NH2:1][C:2]1[C:3]([C:24](=[S:28])[NH2:25])=[N:4][C:5]([C:14]2[CH:19]=[CH:18][C:17](=[O:20])[N:16]([CH:21]([CH3:23])[CH3:22])[N:15]=2)=[C:6]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:7]=1

Participants

Conditions

Temperature: 102.5 °C

Procedure

To a suspension of 3-amino-6-(1-isopropyl-6-oxo-1,6-dihydro-3-pyridazinyl)-5-phenyl-2-pyrazinecarbonitrile (665 mg) and thioacetamide (451 mg) in DMF (3.2 ml) was added a 4N hydrogen chloride solution of dioxane (3.2 ml) and the mixture was stirred at 100-105° C. for 2 hours. Water (65 ml) was added to the mixture to yield a precipitate. The precipitate was collected by filtration, subjected to column chromatography on silica gel eluting with a mixture of n-hexane and EtOAc (40:60 v/v) to give a solid. The solid triturated with acetone and collected by filtration to give 3-amino-6-(1-isopropyl-6-oxo-1,6-dihydro-3-pyridazinyl)-5-phenyl-2-pyrazinecarbothioamide as a solid (417 mg).

Workup

customto yield a precipitate
filtrationThe precipitate was collected by filtration
additionsubjected to column chromatography on silica gel eluting with a mixture of n-hexane and EtOAc (40:60 v/v)
customto give a solid
customThe solid triturated with acetone
filtrationcollected by filtration

Sources & evidence

ORD record: ord-0743f1c41020461abecd1ad66686adba
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07265120B2

Reaction notes

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