Lithium Hydroxide → 2-(4-(3-(6-Fluoropyridin-2-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-c]pyridin-5-yl)-1H-pyrazol-1-yl)acetic acid

HRID 1775005Notes

Reaction equation

HRID 1775005 reaction equation
[F:1][C:2]1[N:7]=[C:6]([C:8]2[C:16]3[C:11](=[CH:12][N:13]=[C:14]([C:17]4[CH:18]=[N:19][N:20]([CH2:22][C:23]([O:25]CC)=[O:24])[CH:21]=4)[CH:15]=3)[N:10]([CH:28]3[CH2:33][CH2:32][CH2:31][CH2:30][O:29]3)[N:9]=2)[CH:5]=[CH:4][CH:3]=1.[OH-].[Li+]>CO.O1CCCC1>[F:1][C:2]1[N:7]=[C:6]([C:8]2[C:16]3[C:11](=[CH:12][N:13]=[C:14]([C:17]4[CH:18]=[N:19][N:20]([CH2:22][C:23]([OH:25])=[O:24])[CH:21]=4)[CH:15]=3)[N:10]([CH:28]3[CH2:33][CH2:32][CH2:31][CH2:30][O:29]3)[N:9]=2)[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 71253737Ethyl 2-(4-(3-(6-fluoropyridin-2-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-c]pyridin-5-yl)-1H-pyrazol-1-yl)acetate

Product 1

HCID 712535612-(4-(3-(6-Fluoropyridin-2-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-c]pyridin-5-yl)-1H-pyrazol-1-yl)acetic acidYield 88.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 100 mg (0.22 mmol) of ethyl 2-(4-(3-(6-fluoropyridin-2-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-c]pyridin-5-yl)-1H-pyrazol-1-yl)acetate and 1 ml of 1 M aqueous solution of lithium hydroxide in 6 ml of methanol and 2 ml of tetrahydrofuran was stirred for 2 hours. The mixture was concentrated in vacuum and neutralized to pH 5 by careful addition of 1 N aqueous HCl. The product was collected by filtration, washed with water and dried in high vacuum to afford 82 mg (85%) of 2-(4-(3-(6-Fluoropyridin-2-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-c]pyridin-5-yl)-1H-pyrazol-1-yl)acetic acid. ESI MS m/z 423.0 (M+1).

Workup

  1. concentrationThe mixture was concentrated in vacuum
  2. additionneutralized to pH 5 by careful addition of 1 N aqueous HCl
  3. filtrationThe product was collected by filtration
  4. washwashed with water
  5. customdried in high vacuum

Sources & evidence

ORD record
ord-20cd7ff75ce34c82820cebf59ab654c6
Source dataset
uspto-grants-2016_02
Patent number
US09260425B2

Reaction notes

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