Water → HCID 86721280, compound

HRID 1750438Notes

Reaction equation

HRID 1750438 reaction equation
[C:1]([N:5]1[C:9]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)=[C:8]([C:18]2[S:19][CH:20]=[C:21]([CH2:23][OH:24])[N:22]=2)[CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2].O>CS(C)=O>[C:1]([N:5]1[C:9]([C:10]2[CH:11]=[CH:12][C:13]([O:16][CH3:17])=[CH:14][CH:15]=2)=[C:8]([C:18]2[S:19][CH:20]=[C:21]([CH:23]=[O:24])[N:22]=2)[CH:7]=[N:6]1)([CH3:3])([CH3:4])[CH3:2]

Participants

4

Reactant 2

HCID 962WaterHCID 86721279HCID 86721279, compound

Product 1

HCID 86721280HCID 86721280, compoundYield 92.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of the compound (663 mg, 1.93 mmol) obtained in step 2 and TEA (0.807 mL, 5.79 mmol) in DMSO (14 mL) was added a sulfur trioxide-pyridine complex (922 mg, 5.79 mmol) at room temperature, and the mixture was stirred at room temperature for 14 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and dried, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (solvent; ethyl acetate) to give 2-(1-(tert-butyl)-5-(4-methoxyphenyl)-1H-pyrazol-4-yl)thiazole-4-carbaldehyde (607.5 mg, 1.779 mmol, 92%) as a white powder.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. customdried
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (solvent; ethyl acetate)

Sources & evidence

ORD record
ord-d42dbded06f74deaa4093e6ceffdbc7b
Source dataset
uspto-grants-2015_10
Patent number
US09156837B2

Reaction notes

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