Methyl morpholine oxide → HCID 57497682, compound

HRID 341197Notes

Reaction equation

HRID 341197 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][N:6]2[C:9]([C:12]3[CH:13]=[C:14]([NH:18][C:19]([NH:21][CH2:22][C:23]([F:26])([F:25])[F:24])=[O:20])[CH:15]=[CH:16][CH:17]=3)=[CH:10][N:11]=[C:5]2[CH:4]=1.C[N+]1([O-])CCOCC1>C(Cl)Cl.CCC[N+](CCC)(CCC)CCC.[O-][Ru](=O)(=O)=O>[CH:2]([C:3]1[CH:8]=[CH:7][N:6]2[C:9]([C:12]3[CH:13]=[C:14]([NH:18][C:19]([NH:21][CH2:22][C:23]([F:26])([F:25])[F:24])=[O:20])[CH:15]=[CH:16][CH:17]=3)=[CH:10][N:11]=[C:5]2[CH:4]=1)=[O:1]

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 59320915HCID 59320915, compound

Product 1

HCID 57497682HCID 57497682, compoundYield 14.2%

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-[3-(7-Hydroxymethyl-imidazo[1,2-a]pyridin-3-yl)-phenyl]-3-(2,2,2-trifluoro-ethyl)-urea (1.42 g, 3.90 mmol) and NMO (1.38, 11.7 mmol) in CH2Cl2 (30 ml) with sieves (3 g) at 0° C. was added TPAP (0.14 g, 0.38 mmol). The reaction mixture was allowed to warm to room temperature and stirred for 18 h, before being filtered to remove the sieves. The organic layer was washed with H2O (×2), dried (MgSO4) and the solvent removed in vacuo. The residue was purified by silica column chromatography (0-60% MeOH in Et2O) to afford the product (0.2 g). MS: [M+H]+=363

Workup

  1. filtrationbefore being filtered
  2. customto remove the sieves
  3. washThe organic layer was washed with H2O (×2)
  4. dry with materialdried (MgSO4)
  5. customthe solvent removed in vacuo
  6. customThe residue was purified by silica column chromatography (0-60% MeOH in Et2O)

Sources & evidence

ORD record
ord-62e41d293863460daf2d550ef9353362
Source dataset
uspto-grants-2014_11
Patent number
US08895745B2

Reaction notes

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