Potassium Hydroxide → HCID 25261751, compound

HRID 383273Notes

Reaction equation

HRID 383273 reaction equation
[N:1]1([C:6]2[CH:7]=[C:8]([C:12]3[N:16]4[CH:17]=[CH:18][C:19]([C:21]5[CH:22]=[N:23][CH:24]=[C:25]([CH:28]=5)[C:26]#[N:27])=[CH:20][C:15]4=[N:14][CH:13]=3)[CH:9]=[CH:10][CH:11]=2)[CH:5]=[CH:4][CH:3]=[N:2]1.[OH-:29].[K+]>CC(O)(C)C>[N:1]1([C:6]2[CH:7]=[C:8]([C:12]3[N:16]4[CH:17]=[CH:18][C:19]([C:21]5[CH:22]=[N:23][CH:24]=[C:25]([CH:28]=5)[C:26]([NH2:27])=[O:29])=[CH:20][C:15]4=[N:14][CH:13]=3)[CH:9]=[CH:10][CH:11]=2)[CH:5]=[CH:4][CH:3]=[N:2]1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 25261426HCID 25261426, compound

Product 1

HCID 25261751HCID 25261751, compound

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Conditions

Temperature
85 °C

Procedure

5-[3-(3-pyrazol-1-yl-phenyl)-imidazo-[1,2-a]-pyridin-7-yl]-nicotinonitrile (Ex. 1.8) (1 eq, 0.099 mmol, 40 mg) and potassium hydroxide (10 eq, 0.99 mmol, 64.8 mg) are dissolved in tBuOH (2 ml) and the reaction mixture is heated at 85° C. for 1.5 h. At the completion of this time the solvent is removed in vacuo and the reaction mixture is diluted with NaHCO3. The aqueous phase is extracted with EtOAc. The organic layer is washed with brine, dried over MgSO4, filtered and evaporated to dryness. The reaction mixture is purified by flash chromatography on silica eluting with DCM/MeOH 9/1 to yield 5-[3-(3-pyrazol-1-yl-phenyl)-imidazo-[1,2-a]pyridin-7-yl]-nicotinamide as a yellow solid; [M+H]+=381

Workup

  1. customAt the completion of this time the solvent is removed in vacuo
  2. additionthe reaction mixture is diluted with NaHCO3
  3. extractionThe aqueous phase is extracted with EtOAc
  4. washThe organic layer is washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated to dryness
  8. customThe reaction mixture is purified by flash chromatography on silica eluting with DCM/MeOH 9/1

Sources & evidence

ORD record
ord-11564801b0eb4e25b9d83a41fc767a24
Source dataset
uspto-grants-2013_02
Patent number
US08367662B2

Reaction notes

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