Methyl morpholine oxide → 1-{3-[8-(1-Ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazin-3-yl]-2-methyl-imidazo[1,2-a]pyridin-8-yl}-ethanone

HRID 226050Notes

Reaction equation

HRID 226050 reaction equation
[CH2:1]([CH:3]([C:6]1[C:7]2[N:8]([C:13]([C:17]3[N:21]4[CH:22]=[CH:23][CH:24]=[C:25]([CH:26]([OH:28])[CH3:27])[C:20]4=[N:19][C:18]=3[CH3:29])=[C:14]([CH3:16])[N:15]=2)[N:9]=[C:10]([CH3:12])[CH:11]=1)[CH2:4][CH3:5])[CH3:2].C[N+]1([O-])CCOCC1>C(Cl)Cl.CCC[N+](CCC)(CCC)CCC.[O-][Ru](=O)(=O)=O>[CH2:1]([CH:3]([C:6]1[C:7]2[N:8]([C:13]([C:17]3[N:21]4[CH:22]=[CH:23][CH:24]=[C:25]([C:26](=[O:28])[CH3:27])[C:20]4=[N:19][C:18]=3[CH3:29])=[C:14]([CH3:16])[N:15]=2)[N:9]=[C:10]([CH3:12])[CH:11]=1)[CH2:4][CH3:5])[CH3:2]

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 577527071-{3-[8-(1-Ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazin-3-yl]-2-methyl-imidazo[1,2-a]pyridin-8-yl}-ethanol

Product 1

HCID 577526751-{3-[8-(1-Ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazin-3-yl]-2-methyl-imidazo[1,2-a]pyridin-8-yl}-ethanoneYield 82.1%

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 1-{3-[8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazin-3-yl]-2-methyl-imidazo[1,2-a]pyridin-8-yl}-ethanol (0.77 g, 1.96 mmol) dissolved in CH2Cl2 (20 mL) is cooled to 0° C., treated with NMO (0.34 g, 2.94 mmol) and TPAP (34 mg, 0.098 mmol). The reaction is stirred at 0° C. for 10 min, then at RT for 4 h. It is filtered through silica gel, washed with EtOAc. Purification of the crude material by silica gel chromatography gives the title compound (0.63 g, 1.61 mmol, 82%) as a yellow solid. 1H NMR (CDCl3): δ 0.92 (t, J=7.5 Hz, 3H), 0.93 (t, J=7.5 Hz, J=7.5 Hz, 3H), 1.80-1.95 (m, 4H), 2.43 (s, 3H), 2.45 (s, 3H), 2.48 (s, 3H), 3.12 (s, 3H), 3.34-3.46 (m, 1H), 6.75 (s, 1H), 6.83 (t, J=7.0 Hz, 1H), 7.67 (dd, J=7.1, 1.4 Hz, 1H), 7.91 (dd, J=7.1, 1.4 Hz, 1H) ppm. ES-MS (m/z): calcd for C23H27N5O (M+H)+: 390.5. found: 390.2.

Workup

  1. waitat RT for 4 h
  2. filtrationIt is filtered through silica gel
  3. washwashed with EtOAc
  4. customPurification of the crude material by silica gel chromatography

Sources & evidence

ORD record
ord-f50aa3c5a274460388331538725d77c6
Source dataset
uspto-grants-2009_07
Patent number
US07557103B2

Reaction notes

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