Hydrochloric Acid → HCID 69332575, compound

HRID 915074Notes

Reaction equation

[H-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.[NH2:11][C:12]1[N:13]=[C:14]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:15]([C:22]2[CH:23]=[CH:24][C:25](=[O:31])[N:26]([CH:28]([CH3:30])[CH3:29])[N:27]=2)=[N:16][C:17]=1S(C)(=O)=O.Cl>CC(N(C)C)=O>[NH2:11][C:12]1[N:13]=[C:14]([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[C:15]([C:22]2[CH:23]=[CH:24][C:25](=[O:31])[N:26]([CH:28]([CH3:30])[CH3:29])[N:27]=2)=[N:16][C:17]=1[O:10][C:7]1[CH:8]=[CH:9][C:4]([F:3])=[CH:5][CH:6]=1

Participants

Conditions

Temperature: 27.5 °C

Procedure

To a suspension of NaH (60% in oil suspension) (31.1 mg) in DMA (0.6 ml) was added 4-fluorophenol (87.3 mg) and the mixture was stirred at 25-30° C. for 30 minutes. 6-[5-Amino-6-(methylsulfonyl)-3-phenyl-2-pyrazinyl]-2-isopropyl-3(2H)-pyridazinone (150 mg) was added and the mixture was heated at 100-105° C. for 15 hours. After addition of 0.1N HCl (3 ml), an aqueous layer was removed by decantation to give a residue. The residue was purified by column chromatography on silica gel eluting with a mixture of n-hexane and EtOAc (60:40 v/v) to give a solid. The solid was crystallized from a mixture of acetone and n-hexane to give 6-[5-amino-6-(4-fluorophenoxy)-3-phenyl-2-pyrazinyl]-2-isopropyl-3(2H)-pyridazinone (70 mg)

Workup

temperaturethe mixture was heated at 100-105° C. for 15 hours
customan aqueous layer was removed by decantation
customto give a residue
customThe residue was purified by column chromatography on silica gel eluting with a mixture of n-hexane and EtOAc (60:40 v/v)
customto give a solid
customThe solid was crystallized from a mixture of acetone and n-hexane

Sources & evidence

ORD record: ord-313686febc894c15b248c4690240ec68
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07265120B2

Reaction notes

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