Sodium Hydroxide → 4-(Cyclopentylamino)-1-ethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid

HRID 490873Notes

Reaction equation

[CH:1]1([NH:6][C:7]2[C:12]([C:13]([O:15]CC)=[O:14])=[CH:11][N:10]=[C:9]3[N:18]([CH2:21][CH3:22])[N:19]=[CH:20][C:8]=23)[CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+]>C(O)C.O>[CH:1]1([NH:6][C:7]2[C:12]([C:13]([OH:15])=[O:14])=[CH:11][N:10]=[C:9]3[N:18]([CH2:21][CH3:22])[N:19]=[CH:20][C:8]=23)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

Conditions

Temperature: 50 °C

Procedure

A solution of Intermediate 2 (2.2 g) in ethanol: water (95:5, 16.85 ml) was treated with sodium hydroxide (1.2 g) and heated at 50° C. for 16 h. The mixture was concentrated in vacuo and the residue re-dissolved in water (0.85 ml). The solution was acidified to pH4 using acetic acid and the resultant white precipitate was collected by filtration and dried under vacuum to afford Intermediate 3 (1.9 g). LCMS showed MH+=275; TRET=2.65 min

Workup

concentrationThe mixture was concentrated in vacuo
dissolutionthe residue re-dissolved in water (0.85 ml)
filtrationthe resultant white precipitate was collected by filtration
customdried under vacuum

Sources & evidence

ORD record: ord-e56f33c2f873417bb5196ca435b95bfa
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07528148B2

Reaction notes

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