Methyl morpholine oxide → HCID 22612297, compound

HRID 844062Notes

Reaction equation

HRID 844062 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([O:7][C:8]2[N:29]=[CH:28][CH:27]=[CH:26][C:9]=2[C:10]([NH:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([CH:20]([OH:25])[C:21]([F:24])([F:23])[F:22])=[CH:16][CH:15]=2)=[O:11])[CH:2]=1.C[N+]1([O-])CCOCC1>C(Cl)Cl.CCC[N+](CCC)(CCC)CCC.[O-][Ru](=O)(=O)=O>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([O:7][C:8]2[N:29]=[CH:28][CH:27]=[CH:26][C:9]=2[C:10]([NH:12][CH2:13][C:14]2[CH:15]=[CH:16][C:17]([C:20](=[O:25])[C:21]([F:24])([F:22])[F:23])=[CH:18][CH:19]=2)=[O:11])[CH:2]=1

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 22612269HCID 22612269, compound

Product 1

HCID 22612297HCID 22612297, compoundYield 43.2%

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2-(Pyridin-3-yloxy)-N-[4-(2,2,2-trifluoro-1-hydroxy-ethyl)-benzyl]-nicotinamide (0.350 grams, 0.87 mmole), NMO (0.153 grams, 1.3 mmole) and 4 Å molecular sieves (0.5 g) in methylene chloride was added TPAP (0.015 grams, 0.04 mmole) and stirred at room temperature for 4 hours. The mixture was filtered through celite, washed with water, dried over MgSO4, filtered and concentrated under reduced pressure to give an oil which was purified by chromatography on silica eluting with 5% methanol/methylene chloride to give a solid (0.151 g). M.P. 134-136°C.; Anal. calcd. for C20H14N3O3F3: C, 59.85; H, 3.52; N, 10.47. Found: C, 59.56; H, 3.63; N, 10.20.

Workup

  1. filtrationThe mixture was filtered through celite
  2. washwashed with water
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customto give an oil which
  7. customwas purified by chromatography on silica eluting with 5% methanol/methylene chloride

Sources & evidence

ORD record
ord-2bbc92e6b8a74aaaaec3949a00485eca
Source dataset
uspto-grants-2002_04
Patent number
US06380218B1

Reaction notes

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