Triethylamine → HCID 86602401, compound

HRID 2373218Notes

Reaction equation

HRID 2373218 reaction equation
[CH2:1]([N:3]1[C:7]2=[N:8][C:9]([CH2:21][O:22][CH3:23])=[C:10]([CH2:19][OH:20])[C:11]([C:12]3[CH:13]=[N:14][CH:15]=[C:16]([CH3:18])[CH:17]=3)=[C:6]2[CH:5]=[N:4]1)[CH3:2].CCN(CC)CC>O>[CH2:1]([N:3]1[C:7]2=[N:8][C:9]([CH2:21][O:22][CH3:23])=[C:10]([CH:19]=[O:20])[C:11]([C:12]3[CH:13]=[N:14][CH:15]=[C:16]([CH3:18])[CH:17]=3)=[C:6]2[CH:5]=[N:4]1)[CH3:2]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 11688198HCID 11688198, compound

Product 1

HCID 86602401HCID 86602401, compoundYield 78.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of [1-ethyl-6-(methoxymethyl)-4-(5-methyl-3-pyridyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]methanol (110 mg), Et3N (0.29 ml) in N,N-dimethylsulfoxide (3 ml) was added sulfur trioxide-pyridine complex (168 mg) at room temperature and the mixture was stirred at room temperature for 1 hour. The reaction mixture was diluted with water and extracted with EtOAc. The organic layer was washed with saturated aqueous ammonium chloride, saturated aqueous NaHCO3, water, brine, dried over anhydrous MgSO4 and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluting with a mixture of EtOAc and n-hexane(3:1) to give 1-ethyl-6-(methoxymethyl)-4-(5-methyl-3-pyridyl)-1H-pyrazolo[3,4-b]pyridine-5-carbaldehyde (86 mg) as a white crystal.

Workup

  1. additionwas added sulfur trioxide-pyridine complex (168 mg) at room temperature
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with saturated aqueous ammonium chloride, saturated aqueous NaHCO3, water, brine
  4. dry with materialdried over anhydrous MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column chromatography on silica gel eluting with a mixture of EtOAc and n-hexane(3:1)

Sources & evidence

ORD record
ord-9eb622de1a38483d8ce4312c8ea10da1
Source dataset
uspto-grants-2008_12
Patent number
US07459451B2

Reaction notes

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