Hydrochloric Acid → HCID 136169016, compound

HRID 336861Notes

Reaction equation

HRID 336861 reaction equation
[C:1]([C:3]1[C:4]([C:19]2[O:23][C:22]([CH3:24])=[C:21]([C:25]([O:27]C)=[O:26])[CH:20]=2)=[C:5]2[CH:18]=[N:17][NH:16][C:6]2=[N:7][C:8]=1[C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)#[N:2].[OH-].[Li+].O.Cl>O1CCOCC1.O>[C:1]([C:3]1[C:4]([C:19]2[O:23][C:22]([CH3:24])=[C:21]([C:25]([OH:27])=[O:26])[CH:20]=2)=[C:5]2[CH:18]=[N:17][NH:16][C:6]2=[N:7][C:8]=1[C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)#[N:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 136353012HCID 136353012, compound

Product 1

HCID 136169016HCID 136169016, compoundYield 8.3%

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

To a suspension of 0.066 g (0.10 mmol) of methyl 5-(5-cyano-6-(4-hydroxyphenyl)-1H-pyrazolo[3,4-b]pyridine-4-yl)-2-methylfuran-3-carboxylate in 2 ml of dioxane/water (80:20) are added 0.011 g (0.4 mmol) of lithium hydroxide. The mixture is brought to 50° C. for 5 h. After return to room temperature, the mixture is poured onto 20 ml of iced water and adjusted to pH=1-2 with 0.1N hydrochloric acid solution. The solution is left to stand for 18 h at 4° C. The precipitate obtained is filtered. The residue obtained is purified by preparative reverse-phase HPLC (acetonitrile/water eluent) to yield 3 mg (6%) of 5-(5-cyano-6-(4-hydroxyphenyl)-1H-pyrazolo[3,4-b]pyridine-4-yl)-2-methylfuran-3-carboxylic acid in the form of a yellow solid.

Workup

  1. waitThe solution is left
  2. waitto stand for 18 h at 4° C
  3. customThe precipitate obtained
  4. filtrationis filtered
  5. customThe residue obtained
  6. customis purified by preparative reverse-phase HPLC (acetonitrile/water eluent)

Sources & evidence

ORD record
ord-dcedd2d78fde45a7bda17bbb32ccb4cd
Source dataset
uspto-grants-2014_11
Patent number
US08889711B2

Reaction notes

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