1,4-Dioxane → HCID 178519498, compound

HRID 931259Notes

Reaction equation

HRID 931259 reaction equation
[CH2:1]([C:8]1[NH:29][C:11]2=[N:12][C:13]([N:16]3[CH2:21][CH2:20][CH2:19][C@@H:18]([C:22]([N:24]4[CH2:28][CH2:27][CH2:26][CH2:25]4)=[O:23])[CH2:17]3)=[CH:14][CH:15]=[C:10]2[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:30]1CCOCC1>[O-2].[Mn+4].[O-2]>[C:1]([C:8]1[NH:29][C:11]2=[N:12][C:13]([N:16]3[CH2:21][CH2:20][CH2:19][C@@H:18]([C:22]([N:24]4[CH2:28][CH2:27][CH2:26][CH2:25]4)=[O:23])[CH2:17]3)=[CH:14][CH:15]=[C:10]2[N:9]=1)(=[O:30])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 312751,4-DioxaneHCID 178521024HCID 178521024, compound

Product 1

HCID 178519498HCID 178519498, compound

Reagents, catalysts & solvents 1

HCID 178418406HCID 178418406, compoundCatalyst

Conditions

Temperature
120 °C

Procedure

Manganese (IV) oxide (2 g) was added to a solution of (R)-(1-(2-benzyl-3H-imidazo[4,5-b]pyridin-5-yl)piperidin-3-yl)(pyrrolidin-1-yl)methanone (200 mg, 0.51 mmol) in dioxane (30 mL). After heating at 120° C. for 48 h in a sealed tube, the mixture was filtered through a pad of Celite and washed with ethyl acetate. The filtrate was concentrated in vacuo and the resulting residue was purified via preparative TLC to afford (R)-(1-(2-benzoyl-3H-imidazo[4,5-b]pyridin-5-yl)piperidin-3-yl)(pyrrolidin-1-yl)methanone (80 mg). MS (ES+APCI) (M+H) 404.1; LCMS retention time 2.855 min (Method G).

Workup

  1. filtrationthe mixture was filtered through a pad of Celite
  2. washwashed with ethyl acetate
  3. concentrationThe filtrate was concentrated in vacuo
  4. customthe resulting residue was purified via preparative TLC

Sources & evidence

ORD record
ord-dde46eae577d495a8c19804e2aa9395f
Source dataset
uspto-grants-2016_03
Patent number
US09296745B2

Reaction notes

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