Trimethyl orthoacetate → 3-Cyclohexyl-2-methyl-3H-imidazo[4,5-b]pyridin-5-ol

HRID 1890350Notes

Reaction equation

HRID 1890350 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([OH:15])=[N:6][C:7]=1[NH:8][CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1.[C:16](OC)(OC)(OC)[CH3:17]>C(O)(C(F)(F)F)=O>[CH:9]1([N:8]2[C:7]3=[N:6][C:5]([OH:15])=[CH:4][CH:3]=[C:2]3[N:1]=[C:16]2[CH3:17])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

4

Reactant 2

HCID 15050Trimethyl orthoacetateHCID 178507771HCID 178507771, compound

Product 1

HCID 1784322233-Cyclohexyl-2-methyl-3H-imidazo[4,5-b]pyridin-5-olYield 5.4%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidCatalyst

Procedure

5-Amino-6-(cyclohexylamino) pyridin-2-ol (0.1 g, 0.482 mmol) was dissolved in trimethyl orthoacetate (3.0 mL, 27.4 mmol). Several drops of TFA were added and the reaction mixture was stirred at room temperature overnight. The reaction mixture was concentrated and the residues were diluted with water/acetonitrile (1:1). The mixture was purified via HPLC to give the title compound (0.006 g). LCMS m/z=232.30 [M+H]+; 1H NMR (400 MHz, methanol-d4) δ ppm 1.43-1.5 (m, 1H), 1.53-1.63 (m, 2H), 1.83 (d, J=11.87 Hz, 1H), 2.01 (d, J=10.99 Hz, 4H), 2.64-2.74 (m, 2H), 2.89 (s, 3H), 4.51-4.57 (m, 1H), 6.90 (d, J=8.8 Hz, 1H), 8.0 (d, J=8.8 Hz, 1H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionthe residues were diluted with water/acetonitrile (1:1)
  3. customThe mixture was purified via HPLC

Sources & evidence

ORD record
ord-7899fc7758d54be3806011d7e271823b
Source dataset
uspto-grants-2013_08
Patent number
US08507473B2

Reaction notes

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