Chloroform → HCID 59326806, compound

HRID 1880073Notes

Reaction equation

HRID 1880073 reaction equation
[NH:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[N:3]=[C:2]1[CH:10]([C:12]1[CH:17]=[CH:16][C:15]([O:18][C:19]2[C:24]([CH:25]3[CH2:30][CH2:29][O:28][CH2:27][CH2:26]3)=N[CH:22]=[CH:21][N:20]=2)=[CH:14][CH:13]=1)[OH:11].[CH:31](Cl)(Cl)Cl>[O-2].[O-2].[Mn+4]>[NH:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[N:3]=[C:2]1[C:10]([C:12]1[CH:13]=[CH:14][C:15]([O:18][C:19]2[C:24]([CH:25]3[CH2:26][CH2:27][O:28][CH2:29][CH2:30]3)=[CH:31][CH:22]=[CH:21][N:20]=2)=[CH:16][CH:17]=1)=[O:11]

Participants

4

Reactant 2

HCID 6212ChloroformHCID 67426636HCID 67426636, compound

Product 1

HCID 59326806HCID 59326806, compound

Reagents, catalysts & solvents 1

HCID 178418406HCID 178418406, compoundCatalyst

Procedure

To a round bottomed flask was added (1H-imidazo[4,5-b]pyridin-2-yl)(4-(3-(tetrahydro-2H-pyran-4-yl)pyrazin-2-yloxy)phenyl)methanol (0.992 g, 2.459 mmol) and manganese dioxide (1.069 g, 12.29 mmol) to stir in chloroform (8.20 mL) for 1 hr. Reaction was filtered through celite. The crude product was purified by reverse-phase preparative HPLC using a Phenomenex Synergi column, 4 micron, MAX-RP, 80 Å, 150×30 mM, 0.1% TFA in ACN/H2O, gradient 40% to 80% over 18 min to provide (1H-Imidazo[4,5-b]pyridin-2-yl)(4-(3-(tetrahydro-2H-pyran-4-yl)pyridin-2-yloxy)phenyl)methanone. MS (ESI, pos. ion) m/z: 401.9 (M+1). IC50 (uM) +++++.

Workup

  1. customReaction
  2. filtrationwas filtered through celite
  3. customThe crude product was purified by reverse-phase preparative HPLC
  4. customover 18 min

Sources & evidence

ORD record
ord-88fa16c7ece64d4db18cea17eb3319d6
Source dataset
uspto-grants-2012_11
Patent number
US08318718B2

Reaction notes

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