Water → HCID 68014858, compound

HRID 1747822Notes

Reaction equation

HRID 1747822 reaction equation
[CH3:1][O:2][C:3]1[C:4]([OH:20])=[C:5]([C:9]2[N:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[N:12]=[CH:11][CH:10]=2)[N:6]=[N:7][CH:8]=1.CS(O[CH:26]1[CH2:29][N:28]([CH:30]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH2:27]1)(=O)=O.C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C=O)C>[C:31]1([CH:30]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[N:28]2[CH2:29][CH:26]([N:7]3[CH:8]=[C:3]([O:2][CH3:1])[C:4](=[O:20])[C:5]([C:9]4[N:13]([C:14]5[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=5)[N:12]=[CH:11][CH:10]=4)=[N:6]3)[CH2:27]2)[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 27587161-(Diphenylmethyl)azetidin-3-yl methanesulfonateHCID 178493808HCID 178493808, compound

Product 1

HCID 68014858HCID 68014858, compoundYield 9.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A suspension of 5-methoxy-3-(1-phenyl-1H-pyrazol-5-yl)pyridazin-4-ol (200 mg), 1-(diphenylmethyl)azetidin-3-yl methanesulfonate (354 mg) and cesium carbonate (729 mg) in DMF (5 mL) was stirred at 100° C. for 12 hr, and water was added. The reaction mixture was extracted with ethyl acetate, the extract was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (35 mg).

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate
  2. dry with materialthe extract was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-e1d82ed73df74c8e806b2be32a33917e
Source dataset
uspto-grants-2015_10
Patent number
US09150588B2

Reaction notes

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