Methanol → HCID 46203371, compound

HRID 524159Notes

Reaction equation

HRID 524159 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[C:15]([CH3:17])([CH3:16])[C:14](=[O:18])[N:13]([CH:19]3[CH2:24][CH2:23][N:22]([S:25]([C:28]4[CH:29]=[C:30]([CH:34]=[CH:35][CH:36]=4)[C:31]([OH:33])=[O:32])(=[O:27])=[O:26])[CH2:21][CH2:20]3)[N:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].S(=O)(=O)(O)O.[CH3:42]O>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[C:15]([CH3:17])([CH3:16])[C:14](=[O:18])[N:13]([CH:19]3[CH2:24][CH2:23][N:22]([S:25]([C:28]4[CH:29]=[C:30]([CH:34]=[CH:35][CH:36]=4)[C:31]([O:33][CH3:42])=[O:32])(=[O:26])=[O:27])[CH2:21][CH2:20]3)[N:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 46203370HCID 46203370, compound

Product 1

HCID 46203371HCID 46203371, compound

Procedure

0.5 g 3-({4-[3-(3,4-Dimethoxyphenyl)-4,4-dimethyl-5-oxo-4,5-dihydro-1H-pyrazol-1-yl]piperidin-1-yl}sulfonyl)benzoic acid (compound described in example 25) are suspended in 20 ml of methanol, 0.2 ml concentrated sulfuric acid are added, and the reaction mixture is heated to reflux for 24 h. The solvent is removed under reduced pressure, the residue is taken up in DCM, the organic phase is washed with aqueous sodium carbonate solution (5%) and dried over MgSO4. The solvents are evaporated under reduced pressure and the crude product is crystallized from DCM and diethyl ether to yield the title compound.

Workup

  1. temperaturethe reaction mixture is heated
  2. temperatureto reflux for 24 h
  3. customThe solvent is removed under reduced pressure
  4. washthe organic phase is washed with aqueous sodium carbonate solution (5%)
  5. dry with materialdried over MgSO4
  6. customThe solvents are evaporated under reduced pressure
  7. customthe crude product is crystallized from DCM and diethyl ether

Sources & evidence

ORD record
ord-f6b04691e31a4210880a67c856662400
Source dataset
uspto-grants-2016_05
Patent number
US09340522B2

Reaction notes

Loading…