Hydrochloric Acid → HCID 68284673, compound

HRID 571605Notes

Reaction equation

[CH2:1]([C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[C:5]([CH2:10][CH3:11])[C:4]=1[C:12]1[C:13](=[O:31])[N:14]([CH3:30])[N:15]=[C:16]([CH2:28][OH:29])[C:17]=1S(C1C=CC(C)=CC=1)(=O)=O)[CH3:2].[OH-:32].[Na+].Cl>CN1CCN(C)C1=O>[CH2:1]([C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[C:5]([CH2:10][CH3:11])[C:4]=1[C:12]1[C:13](=[O:31])[N:14]([CH3:30])[N:15]=[C:16]([CH2:28][OH:29])[C:17]=1[OH:32])[CH3:2]

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of 4-(2,6-diethyl-4-methylphenyl)-6-hydroxymethyl-5-(4-methylphenylsulfonyl)-2-methyl-3(2H)-pyridazinone (2.58 g, 5.85 mmol) in 1,3-dimethylimidazolidinone (30 ml) was added 2N aqueous sodium hydroxide solution (15 ml), and stirred at 70° C. for 12 hours. After cooling to room temperature, 2N hydrochloric acid (25 ml) was added, and extracted with ethyl acetate 2 times. The combined organic layer was washed with water 2 times, washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1 to 1:2) to give 842 mg of Compound (I-24-1) (yield: 47%) as solid.

Workup

temperatureAfter cooling to room temperature
extractionextracted with ethyl acetate 2 times
washThe combined organic layer was washed with water 2 times
washwashed with saturated brine
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1 to 1:2)

Sources & evidence

ORD record: ord-46b62802a4244a9ab4279b6f528a135f
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09029295B2

Reaction notes

Loading…