Potassium Hydroxide → (6-Methoxy-pyrazolo[1,5-b]pyridazin-3-yl)-(3,4,5-trimethoxy-phenyl)-methanone

HRID 273345Notes

Reaction equation

C(=O)(O)[O-].[K+].[NH2:6]OS(O)(=O)=O.[CH3:12][O:13][C:14]1[N:15]=[N:16][CH:17]=[CH:18][CH:19]=1.[CH3:20][O:21][C:22]1[CH:23]=[C:24]([C:32](=[O:35])[C:33]#[CH:34])[CH:25]=[C:26]([O:30][CH3:31])[C:27]=1[O:28][CH3:29].[OH-].[K+]>C(Cl)Cl>[CH3:12][O:13][C:14]1[CH:19]=[CH:18][C:17]2[N:16]([N:6]=[CH:34][C:33]=2[C:32]([C:24]2[CH:25]=[C:26]([O:30][CH3:31])[C:27]([O:28][CH3:29])=[C:22]([O:21][CH3:20])[CH:23]=2)=[O:35])[N:15]=1

Participants

Conditions

Temperature: 70 °C

Procedure

Potassium bicarbonate (2.5 M) was added to a solution of hydroxylamine-O-sulfonic acid (64.7 mg, 0.57 mmol) until the pH value turned to 5. Then, 3-methoxypyridazine (42 mg, 0.38 mmol) was added at 70° C. over 10 min. The mixture was stirred at 70° C. for 2 h and then cooled to room temperature. The pH value of the mixture was adjusted to 8 by addition of 2.5M potassium bicarbonate. 1-(3,4,5-Trimethoxyphenyl)prop-2-yn-1-one (42 mg, 0.19 mmol) in CH2Cl2 (10 mL) and potassium hydroxide (40 mg, 0.71 mmol) were added. The mixture was stirred at room temperature overnight, and then was extracted with CH2Cl2, and the combined organic layers were washed with brine, dried over MgSO4, and concentrated to give a crude product, which was purified on a silica gel column eluting with CH2Cl2/MeOH (20:1) to afford compound 15 as a white solid (31 mg, 48%).

Workup

temperaturecooled to room temperature
stirringThe mixture was stirred at room temperature overnight
extractionwas extracted with CH2Cl2
washthe combined organic layers were washed with brine
dry with materialdried over MgSO4
concentrationconcentrated
customto give a crude product, which
customwas purified on a silica gel column
washeluting with CH2Cl2/MeOH (20:1)

Sources & evidence

ORD record: ord-69926f659b8a4eefae0be08cc5a27929
Source dataset: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07456289B2

Reaction notes

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