Hydrochloric Acid → HCID 136059262, compound

HRID 336856Notes

Reaction equation

HRID 336856 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:14]([C:15]#[N:16])=[C:13]([C:17]3[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][C:18]=3[F:24])[N:12]=[C:11]3[NH:25][N:26]=[CH:27][C:10]=23)=[CH:5][CH:4]=1)#[N:2].[OH-:28].[K+].Cl>C(O)(C)(C)C.O>[C:15]([C:14]1[C:9]([C:6]2[CH:5]=[CH:4][C:3]([C:1]([NH2:2])=[O:28])=[CH:8][CH:7]=2)=[C:10]2[CH:27]=[N:26][NH:25][C:11]2=[N:12][C:13]=1[C:17]1[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][C:18]=1[F:24])#[N:16]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 136353007HCID 136353007, compound

Product 1

HCID 136059262HCID 136059262, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6386tert-ButanolSolvent

Procedure

A solution of 0.06 g (0.17 mmol) of 4-(4-cyanophenyl)-6-(2-fluoro-4-hydroxyphenyl)-1H-pyrazolo[3,4-b]pyridine-5-carbonitrile and 0.08 g (1.40 mmol) of potassium hydroxide in 6 ml of tert-butanol is refluxed for 4 h. The mixture is then cooled to room temperature, diluted with water, acidified with 1N HCl, and extracted with dichloromethane. The organic phase is dried over sodium sulfate, filtered, and concentrated. The solid obtained is then purified by chromatography on silica (methanol gradient in dichloromethane: 0 to 10%) to yield 0.019 g (30%) of 4-(5-cyano-6-(2-fluoro-4-hydroxyphenyl)-1H-pyrazolo[3,4-b]pyridine-4-yl)benzamide in the form of yellow crystals.

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialThe organic phase is dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe solid obtained
  6. customis then purified by chromatography on silica (methanol gradient in dichloromethane: 0 to 10%)

Sources & evidence

ORD record
ord-260ba8a2658b4537a6f506f2f2a4c87c
Source dataset
uspto-grants-2014_11
Patent number
US08889711B2

Reaction notes

Loading…