(8-Morpholinoimidazo[1,2-b]pyridazin-2-yl)methanol → 8-Morpholinoimidazo[1,2-b]pyridazine-2-carbaldehyde

HRID 718569Notes

Reaction equation

HRID 718569 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[C:8]3[N:9]([CH:13]=[C:14]([CH2:16][OH:17])[N:15]=3)[N:10]=[CH:11][CH:12]=2)[CH2:3][CH2:2]1>C(Cl)Cl.[O-2].[Mn+4].[O-2]>[O:1]1[CH2:2][CH2:3][N:4]([C:7]2[C:8]3[N:9]([CH:13]=[C:14]([CH:16]=[O:17])[N:15]=3)[N:10]=[CH:11][CH:12]=2)[CH2:5][CH2:6]1

Participants

4

Reactant 1

HCID 117728752(8-Morpholinoimidazo[1,2-b]pyridazin-2-yl)methanol

Product 1

HCID 1177286388-Morpholinoimidazo[1,2-b]pyridazine-2-carbaldehyde

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of compound 5d (1.7 g, 7.3 mmol) in DCM (244 mL) was added manganese (IV) oxide (10 g, 116 mmol). The mixture was stirred at rt for 18 h, and filtered through a pad of diatomaceous earth. The filtrate was concentrated to give compound 5e as an off-white solid. 1H-NMR (400 MHz, CDCl3) δ (ppm): 10.08 (s, 1H), 8.37 (s, 1H), 8.06 (d, J=5.6 Hz, 1H), 6.09 (d, J=5.6 Hz, 1H), 3.99-4.18 (m, 4H), 3.78-3.99 (m, 4H).

Workup

  1. filtrationfiltered through a pad of diatomaceous earth
  2. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-b697f03905064ea7b16d37820e13d1f1
Source dataset
uspto-grants-2015_11
Patent number
US09193736B2

Reaction notes

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