Hydrochloric Acid → HCID 178481776, compound

HRID 915079Notes

Reaction equation

[H-].[Na+].C1(CC[OH:11])C=CC=CC=1.[NH2:12][C:13]1[N:14]=[C:15]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:16]([C:23]2[CH:24]=[CH:25][C:26](=[O:30])[N:27]([CH3:29])[N:28]=2)=[N:17][C:18]=1S(C)(=O)=O.Cl>>[NH2:12][C:13]1[N:14]=[C:15]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:16]([C:23]2[CH:24]=[CH:25][C:26](=[O:30])[N:27]([CH3:29])[N:28]=2)=[N:17][C:18]=1[OH:11]

Participants

Reactant 4

HCID 313Hydrochloric Acid

HCID 60542-Phenylethanol

HCID 24758Sodium hydride

HCID 69331452HCID 69331452, compound

Product 1

HCID 178481776HCID 178481776, compound

Conditions

Temperature: 27.5 °C

Procedure

To a suspension of NaH (60% in oil suspension) (33.6 mg) in 1,2-dimethyl-2-imidazolidinone (0.6 ml) was added 2-phenylethanol (0.101 ml) and the mixture was stirred at 25-30° C. for 30 minutes. 6-[5-Amino-6-(methylsulfonyl)-3-phenyl-2-pyrazinyl]-2-methyl-3(2H)-pyridazinone (150 mg) was added and the mixture was heated at 100-105° C. for 15 hours. To the mixture was added 0.1N HCl (3 ml) and a precipitate was collected by filtration. The precipitate was suspended in CHCl3 and collected by filtration to give 6-(5-amino-6-hydroxy-3-phenyl-2-pyrazinyl)-2-methyl-3(2H)-pyridazinone (60 mg). The CHCl3 solution was dried over MgSO4, concentrated under reduced pressure and purified by column chromatography on silica gel eluting with a mixture of n-hexane and EtOAc (50:50 v/v) to give a solid. The solid was suspended in acetone and collected by filtration to give 6-[5-amino-3-phenyl-6-(2-phenylethoxy)-2-pyrazinyl]-2-methyl-3(2H)-pyridazinone (7 mg).

Workup

temperaturethe mixture was heated at 100-105° C. for 15 hours
filtrationa precipitate was collected by filtration
filtrationcollected by filtration

Sources & evidence

ORD record: ord-a9465df772fc42c0821c6ec23b378146
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07265120B2

Reaction notes

Loading…