2-(5-(Benzyloxy)-3H-imidazo[4,5-b]pyridin-3-yl)cyclohexanone → HCID 178515950, compound

HRID 1890290Notes

Reaction equation

HRID 1890290 reaction equation
C([O:8][C:9]1[N:14]=[C:13]2[N:15]([CH:18]3[CH2:23][CH2:22][CH2:21][CH2:20][C:19]3=[O:24])[CH:16]=[N:17][C:12]2=[CH:11][CH:10]=1)C1C=CC=CC=1>C(O)C.[Pd]>[OH:8][C:9]1[N:14]=[C:13]2[N:15]([CH:18]3[CH2:23][CH2:22][CH2:21][CH2:20][C:19]3=[O:24])[CH:16]=[N:17][C:12]2=[CH:11][CH:10]=1

Participants

4

Reactant 1

HCID 673135802-(5-(Benzyloxy)-3H-imidazo[4,5-b]pyridin-3-yl)cyclohexanone

Product 1

HCID 178515950HCID 178515950, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

2-(5-(Benzyloxy)-3H-imidazo[4,5-b]pyridin-3-yl)cyclohexanone (0.400 g, 1.25 mmol), was taken up in ethanol (5 mL). Catalytic palladium on carbon was added, and the solution was placed under an atmosphere of hydrogen and stirred at room temperature for 2 days. The solution was then filtered through Celite®. The solvent was removed under reduced pressure and the residue was purified by preparative HPLC to give the title compound. LCMS m/z=232.1 [M+H]+; 1H NMR (400 MHz, CDCl3) δ ppm 1.80-1.95 (m, 1H), 1.95-2.10 (m, 1H), 2.15-2.35 (m, 4H), 2.70-2.50 (m, 2H), 4.50 (dd, J1=13.2 Hz, J2=5.7 Hz, 1H), 6.89 (d, J=8.9 Hz, 1H), 8.16 (d, J=8.9 Hz, 1H), 8.74 (s, 1H).

Workup

  1. filtrationThe solution was then filtered through Celite®
  2. customThe solvent was removed under reduced pressure
  3. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-073f4f72ca4f4296a8c5d2ca80d5f62c
Source dataset
uspto-grants-2013_08
Patent number
US08507473B2

Reaction notes

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