Acetic Acid → HCID 136507827, compound

HRID 2279163Notes

Reaction equation

HRID 2279163 reaction equation
C[O:2][C:3]([C:5]1[C:6]2[C:20]([CH:21]3[CH2:23][CH2:22]3)=[N:19][N:18]([CH:24]3[CH2:29][CH2:28][CH2:27][CH2:26][O:25]3)[C:7]=2[N:8]=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=2)[CH:10]=1)=[O:4].[OH-].[Na+].C(O)(=O)C>C(O)(C)C>[CH:21]1([C:20]2[C:6]3[C:5]([C:3]([OH:4])=[O:2])=[CH:10][C:9]([C:11]4[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=4)=[N:8][C:7]=3[N:18]([CH:24]3[CH2:29][CH2:28][CH2:27][CH2:26][O:25]3)[N:19]=2)[CH2:22][CH2:23]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 137133009HCID 137133009, compound

Product 1

HCID 136507827HCID 136507827, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 3-cyclopropyl-6-(4-hydroxy-phenyl)-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid methyl ester (11.3 g) and sodium hydroxide solution (1N, 100 mL) in isopropanol (100 mL) was stirred at r.t. for 5 h. The mixture was poured onto ice-water and the pH was adjusted to 5 with acetic acid. The mixture was extracted with dichloromethane three times and the combined organic layers were dried over magnesium sulphate, filtrated and concentrated in vacuo. 10.35 g (95%) of the title compound were obtained.

Workup

  1. additionThe mixture was poured onto ice-water
  2. extractionThe mixture was extracted with dichloromethane three times
  3. dry with materialthe combined organic layers were dried over magnesium sulphate
  4. filtrationfiltrated
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-323606a2b2624df98d3e38578d302c50
Source dataset
uspto-grants-2015_09
Patent number
US09133181B2

Reaction notes

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