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Water → Tert-butyl 4-[6-[6-[6-(1,2-dihydroxyethyl)pyrazin-2-yl]pyrazolo[4,3-c]pyridin-1-yl]-2-pyridyl]piperazine-1-carboxylate

HRID 57997
Notes
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Reaction equation

HRID 57997 reaction equation
[CH:1]([C:3]1[N:8]=[C:7]([C:9]2[N:14]=[CH:13][C:12]3[CH:15]=[N:16][N:17]([C:18]4[N:23]=[C:22]([N:24]5[CH2:29][CH2:28][N:27]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:26][CH2:25]5)[CH:21]=[CH:20][CH:19]=4)[C:11]=3[CH:10]=2)[CH:6]=[N:5][CH:4]=1)=[CH2:2].[OH2:37].C[N+]1([O-])CCOCC1.[OH2:46]>CC(C)=O.[Os](=O)(=O)(=O)=O.C(O)(C)(C)C>[OH:37][CH:1]([C:3]1[N:8]=[C:7]([C:9]2[N:14]=[CH:13][C:12]3[CH:15]=[N:16][N:17]([C:18]4[N:23]=[C:22]([N:24]5[CH2:25][CH2:26][N:27]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:28][CH2:29]5)[CH:21]=[CH:20][CH:19]=4)[C:11]=3[CH:10]=2)[CH:6]=[N:5][CH:4]=1)[CH2:2][OH:46]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 962WaterHCID 2724197N-Methylmorpholine N-oxide monohydrateHCID 86707182Tert-butyl 4-[6-[6-(6-vinylpyrazin-2-yl)pyrazolo[4,3-c]pyridin-1-yl]-2-pyridyl]piperazine-1-carboxylate

Product 1

HCID 86707180Tert-butyl 4-[6-[6-[6-(1,2-dihydroxyethyl)pyrazin-2-yl]pyrazolo[4,3-c]pyridin-1-yl]-2-pyridyl]piperazine-1-carboxylateYield 67%

Reagents, catalysts & solvents 3

HCID 6386
tert-Butanol
Catalyst
HCID 30318Osmium TetroxideCatalyst
HCID 180AcetoneSolvent

Procedure

A mixture of tert-butyl 4-[6-[6-(6-vinylpyrazin-2-yl)pyrazolo[4,3-c]pyridin-1-yl]-2-pyridyl]piperazine-1-carboxylate (513 mg; 1.06 mmol), N-methylmorpholine-N-oxide monohydrate (744 mg, 6.35 mmol) and 2.5% solution of osmium tetroxide in tert-butanol (0.6 ml, 0.04764 mmol) in 20 ml of acetone and 2.5 ml of water was stirred at room temperature for 24 hours. The mixture was filtered, mixed with water and extracted with EtOAc. The organic extracts were washed with water, 5% aq. citric acid, sat. aq. NaHCO3, brine, dried over Na2SO4 and concentrated. The residue was triturated with ethyl ether, the precipitate was collected by filtration and washed with ethyl ether affording tert-butyl 4-(6-(6-(6-(1,2-dihydroxyethyl)pyrazin-2-yl)-1H-pyrazolo[4,3-c]pyridin-1-yl)pyridin-2-yl)piperazine-1-carboxylate (424 mg, 67%). MS (ESI) m/z: 519.3 [M+H]+

Workup

  1. filtrationThe mixture was filtered
  2. additionmixed with water
  3. extractionextracted with EtOAc
  4. washThe organic extracts were washed with water, 5% aq. citric acid, sat. aq. NaHCO3, brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customThe residue was triturated with ethyl ether
  8. filtrationthe precipitate was collected by filtration
  9. washwashed with ethyl ether

Sources & evidence

ORD record
ord-5601ac2dc04a4c6d8d504c6258949961
Source dataset
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09434725B2

Reaction notes

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