Selenium Dioxide → 6-chloro-3-morpholino-1-trityl-1H-pyrazolo[4,3-c]pyridine-4-carbaldehyde

HRID 590830Notes

Reaction equation

HRID 590830 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([CH3:8])[C:5]2[C:9]([N:31]3[CH2:36][CH2:35][O:34][CH2:33][CH2:32]3)=[N:10][N:11]([C:12]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:4]=2[CH:3]=1.[Se](=O)=[O:38]>O1CCOCC1>[Cl:1][C:2]1[N:7]=[C:6]([CH:8]=[O:38])[C:5]2[C:9]([N:31]3[CH2:36][CH2:35][O:34][CH2:33][CH2:32]3)=[N:10][N:11]([C:12]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 24007Selenium DioxideHCID 1182716944-(6-chloro-4-methyl-1-trityl-1H-pyrazolo[4,3-c]pyridin-3-yl)morpholine

Product 1

HCID 1182722196-chloro-3-morpholino-1-trityl-1H-pyrazolo[4,3-c]pyridine-4-carbaldehyde

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

4-(6-Chloro-4-methyl-1-trityl-1H-pyrazolo[4,3-c]pyridin-3-yl)morpholine (Example 106, Step 1; 450.9 mg, 0.911 mmol) was dissolved in dioxane (10 mL) and selenium dioxide (303 mg, 2.73 mmol) was added. The reaction mixture was stirred at reflux over the weekend. The reaction was filtered over celite, rinsed with ethyl acetate, and concentrated in vacuo. The residue was diluted with DCM and filtered over celite. The filtrate was concentrated in vacuo while loading onto silica gel. Purification by flash chromatography (5-40% EtOAc/Hexanes) gave 6-chloro-3-morpholino-1-trityl-1H-pyrazolo[4,3-c]pyridine-4-carbaldehyde. MS ESI calc'd. For C30H26ClN4O2 [M+H]+ 509. found 509.

Workup

  1. temperatureat reflux over the weekend
  2. filtrationThe reaction was filtered over celite
  3. washrinsed with ethyl acetate
  4. concentrationconcentrated in vacuo
  5. additionThe residue was diluted with DCM
  6. filtrationfiltered over celite
  7. concentrationThe filtrate was concentrated in vacuo
  8. customPurification by flash chromatography (5-40% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-168fbe2cfe844575b22dad605a48c24e
Source dataset
uspto-grants-2016_01
Patent number
US09233979B2

Reaction notes

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