Sodium periodate → tert-butyl 4-(6-(6-(6-formylpyrazin-2-yl)-1H-pyrazolo[4,3-c]pyridin-1-yl)pyridin-2-yl)piperazine-1-carboxylate

HRID 57994Notes

Reaction equation

HRID 57994 reaction equation
I([O-])(=O)(=O)=O.[Na+].[OH:7][CH:8]([C:11]1[N:16]=[C:15]([C:17]2[N:22]=[CH:21][C:20]3[CH:23]=[N:24][N:25]([C:26]4[N:31]=[C:30]([N:32]5[CH2:37][CH2:36][N:35]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[CH2:34][CH2:33]5)[CH:29]=[CH:28][CH:27]=4)[C:19]=3[CH:18]=2)[CH:14]=[N:13][CH:12]=1)CO>O.O1CCCC1>[CH:8]([C:11]1[N:16]=[C:15]([C:17]2[N:22]=[CH:21][C:20]3[CH:23]=[N:24][N:25]([C:26]4[N:31]=[C:30]([N:32]5[CH2:33][CH2:34][N:35]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[CH2:36][CH2:37]5)[CH:29]=[CH:28][CH:27]=4)[C:19]=3[CH:18]=2)[CH:14]=[N:13][CH:12]=1)=[O:7]

Participants

5

Reactant 2

HCID 23667635Sodium periodateHCID 86707180Tert-butyl 4-[6-[6-[6-(1,2-dihydroxyethyl)pyrazin-2-yl]pyrazolo[4,3-c]pyridin-1-yl]-2-pyridyl]piperazine-1-carboxylate

Product 1

HCID 86707179tert-butyl 4-(6-(6-(6-formylpyrazin-2-yl)-1H-pyrazolo[4,3-c]pyridin-1-yl)pyridin-2-yl)piperazine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolvent3×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of sodium periodate (260 mg 1.22 mmol) in 5 ml of water was added to a solution of tert-butyl 4-[6-[6-[6-(1,2-dihydroxyethyl)pyrazin-2-yl]pyrazolo[4,3-c]pyridin-1-yl]-2-pyridyl]piperazine-1-carboxylate (315 mg, 0.61 mmol) in 25 ml of tetrahydrofuran and 5 ml of water. The mixture was stirred for 24 hours, concentrated, the residue partitioned between ethyl acetate and water, the organic extracts were washed with water, brine, dried over sodium sulfate and concentrated. The residue was purified on 12 g silica gel column eluting with ethyl acetate gradient in heptane to afford 245 mg (83%). MS (ESI) m/z: 505.2 [M+H2O+H]+.

Workup

  1. concentrationconcentrated
  2. customthe residue partitioned between ethyl acetate and water
  3. washthe organic extracts were washed with water, brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified on 12 g silica gel column
  7. washeluting with ethyl acetate gradient in heptane
  8. customto afford 245 mg (83%)

Sources & evidence

ORD record
ord-a69f1c9b161c4fed8ff5f70e1a34e87c
Source dataset
uspto-grants-2016_09
Patent number
US09434725B2

Reaction notes

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