HCID 89690318, compound → 1-(2-Cyclopropyl-3-methylimidazo[1,2-a]pyridin-6-yl)-4-hydroxypyridin-2(1H)-one

HRID 2202944Notes

Reaction equation

HRID 2202944 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][N:12]([C:15]2[CH:16]=[CH:17][C:18]3[N:19]([C:21]([CH3:27])=[C:22]([CH:24]4[CH2:26][CH2:25]4)[N:23]=3)[CH:20]=2)[C:11](=[O:28])[CH:10]=1)C1C=CC=CC=1>CO.[Pd]>[CH:24]1([C:22]2[N:23]=[C:18]3[CH:17]=[CH:16][C:15]([N:12]4[CH:13]=[CH:14][C:9]([OH:8])=[CH:10][C:11]4=[O:28])=[CH:20][N:19]3[C:21]=2[CH3:27])[CH2:26][CH2:25]1

Participants

4

Reactant 1

HCID 89690318HCID 89690318, compound

Product 1

HCID 896902811-(2-Cyclopropyl-3-methylimidazo[1,2-a]pyridin-6-yl)-4-hydroxypyridin-2(1H)-oneYield 58.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a stirred solution of 4-(benzyloxy)-1-(2-cyclopropyl-3-methylimidazo[1,2-a]pyridin-6-yl)pyridin-2(1H)-one (127 mg) in MeOH (8 ml) was added Pd/C (10%, 25 mg), and the mixture was stirred under H2 atmosphere at room temperature for 4 h. The solid was then filtered through Celite, and the filtrate was concentrated in vacuo. The residue was purified by silica gel column chromatography (MeOH/DCM) to give the title compound (56 mg) as an off-white solid.

Workup

  1. filtrationThe solid was then filtered through Celite
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was purified by silica gel column chromatography (MeOH/DCM)

Sources & evidence

ORD record
ord-77fb9223aabb4c2e83e04a4520cc4b86
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

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