HCID 59278246, compound → HCID 59278428, compound

HRID 559782Notes

Reaction equation

HRID 559782 reaction equation
[OH:1][CH:2]([C:4]1[CH:9]=[C:8]([C@@H:10]([NH:13][C:14]([C:16]2[C:17]3[CH:24]=[N:23][N:22]([C:25]4[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=4)[C:18]=3[CH:19]=[N:20][CH:21]=2)=[O:15])[CH2:11][CH3:12])[CH:7]=[CH:6][N:5]=1)[CH3:3]>CC(C)=O.O=[Mn]=O>[C:2]([C:4]1[CH:9]=[C:8]([C@@H:10]([NH:13][C:14]([C:16]2[C:17]3[CH:24]=[N:23][N:22]([C:25]4[CH:26]=[CH:27][C:28]([F:31])=[CH:29][CH:30]=4)[C:18]=3[CH:19]=[N:20][CH:21]=2)=[O:15])[CH2:11][CH3:12])[CH:7]=[CH:6][N:5]=1)(=[O:1])[CH3:3]

Participants

4

Reactant 1

HCID 59278246HCID 59278246, compound

Product 1

HCID 59278428HCID 59278428, compound

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalyst2×HCID 180AcetoneSolvent2×

Procedure

To a solution of 1-(4-fluorophenyl)-1H-pyrazolo[3,4-c]pyridine-4-carboxylic acid {(S)-1-[2-(1-hydroxy-ethyl)-pyridin-4-yl]-propyl}-amide (71 mg, 0.17 mmol) in acetone (4 mL) was added MnO2 (147 mg, 1.69 mmol). After 18 hours, the reaction was monitored by HPLC-MS indicating a 1:3 mixture of product to starting material. The mixture was filtered through diatomaceous earth rinsing with acetone (200 mL) and the filtrate was concentrated in vacuo. The residue was diluted with acetone (4 mL) and MnO2 (147 mg, 1.69 mmol) was added. After 5 hours, the reaction was filtered through diatomaceous earth, rinsed with acetone and the filtrate was concentrated in vacuo. The residue was purified by silica gel chromatography eluting with using a gradient of 10-100% EtOAc in heptane to afford 1-(4-fluorophenyl)-1H-pyrazolo[3,4-c]pyridine-4-carboxylic acid [(S)-1-(2-acetyl-pyridin-4-yl)-propyl]-amide as a white solid.

Workup

  1. additiona 1:3 mixture of product
  2. filtrationThe mixture was filtered through diatomaceous earth
  3. washrinsing with acetone (200 mL)
  4. concentrationthe filtrate was concentrated in vacuo
  5. additionwas added
  6. waitAfter 5 hours
  7. filtrationthe reaction was filtered through diatomaceous earth
  8. washrinsed with acetone
  9. concentrationthe filtrate was concentrated in vacuo
  10. customThe residue was purified by silica gel chromatography
  11. washeluting

Sources & evidence

ORD record
ord-38d7cf55543e4125be4b7a5aa82f0a44
Source dataset
uspto-grants-2011_11
Patent number
US08063065B2

Reaction notes

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