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

HRID 57995
Notes
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Reaction equation

HRID 57995 reaction equation
[BH4-].[Na+].[CH:3]([C:5]1[N:10]=[C:9]([C:11]2[N:16]=[CH:15][C:14]3[CH:17]=[N:18][N:19]([C:20]4[N:25]=[C:24]([N:26]5[CH2:31][CH2:30][N:29]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:28][CH2:27]5)[CH:23]=[CH:22][CH:21]=4)[C:13]=3[CH:12]=2)[CH:8]=[N:7][CH:6]=1)=[O:4]>CO>[OH:4][CH2:3][C:5]1[N:10]=[C:9]([C:11]2[N:16]=[CH:15][C:14]3[CH:17]=[N:18][N:19]([C:20]4[N:25]=[C:24]([N:26]5[CH2:27][CH2:28][N:29]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:30][CH2:31]5)[CH:23]=[CH:22][CH:21]=4)[C:13]=3[CH:12]=2)[CH:8]=[N:7][CH:6]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86707179tert-butyl 4-(6-(6-(6-formylpyrazin-2-yl)-1H-pyrazolo[4,3-c]pyridin-1-yl)pyridin-2-yl)piperazine-1-carboxylate

Product 1

HCID 86707181tert-butyl 4-(6-(6-(6-(hydroxymethyl)pyrazin-2-yl)-1H-pyrazolo[4,3-c]pyridin-1-yl)pyridin-2-yl)piperazine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (25 mg, 0.66 mmol) was added portionwise to a solution of tert-butyl 4-[6-[6-(6-formylpyrazin-2-yl)pyrazolo[4,3-c]pyridin-1-yl]-2-pyridyl]piperazine-1-carboxylate (162 mg, 0.33 mmol) in 6 ml of methanol. The mixture was stirred for 1 hour, concentrated in vacuum, the residue partitioned between ethyl acetate and water. The organic extracts were washed with water, 1% aq. citric acid, water, and brine, dried over sodium sulfate and concentrated. The residue was purified on a 12 g silica gel column eluting with 0-7% gradient of methanol in DCM to afford 125 mg (77%). MS (ESI) m/z: 489.2 [M+H]+

Workup

  1. concentrationconcentrated in vacuum
  2. customthe residue partitioned between ethyl acetate and water
  3. washThe organic extracts were washed with water, 1% aq. citric acid, water, and brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified on a 12 g silica gel column
  7. washeluting with 0-7% gradient of methanol in DCM
  8. customto afford 125 mg (77%)

Sources & evidence

ORD record
ord-0e8c1d3e804a485f81d8238a8652be37
Source dataset
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09434725B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes