Methyl morpholine oxide → HCID 73672704, compound

HRID 1482568Notes

Reaction equation

HRID 1482568 reaction equation
[Cl:1][C:2]1[C:26]([Cl:27])=[CH:25][CH:24]=[CH:23][C:3]=1[C:4]([NH:6][CH2:7][CH:8]([N:16]1[CH2:21][CH2:20][CH:19]([OH:22])[CH2:18][CH2:17]1)[C:9]1[CH:10]=[N:11][C:12]([CH3:15])=[N:13][CH:14]=1)=[O:5].C[N+]1([O-])CCOCC1>C(Cl)Cl.CCC[N+](CCC)(CCC)CCC.[O-][Ru](=O)(=O)=O>[Cl:1][C:2]1[C:26]([Cl:27])=[CH:25][CH:24]=[CH:23][C:3]=1[C:4]([NH:6][CH2:7][CH:8]([C:9]1[CH:14]=[N:13][C:12]([CH3:15])=[N:11][CH:10]=1)[N:16]1[CH2:21][CH2:20][C:19](=[O:22])[CH2:18][CH2:17]1)=[O:5]

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 86716050HCID 86716050, compound

Product 1

HCID 73672704HCID 73672704, compoundYield 24%

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2,3-dichloro-N-(2-(4-hydroxypiperidin-1-yl)-2-(2-methylpyrimidin-5-yl)ethyl)benzamide (130 mg, 0.32 mmol) in DCM (5 mL) was added 4 A molecular sieves (1.3 g), NMO (205 mg, 1.75 mmol) and TPAP (2.2 mg). The mixture was stiffed at room temperature overnight. The resulting mixture was filtered. The filtrate was washed with water, dried over Na2SO4 and concentrated. The residue was purified by preparative TLC (EtOAc:MeC)H=100:3) to give 2,3-dichloro-N-(2-(2-methylpyrimidin-5-yl)-2-(4-oxopiperidin-1-yl)ethyl)benzamide (31 mg, yield: 24%) as a white solid.

Workup

  1. filtrationThe resulting mixture was filtered
  2. washThe filtrate was washed with water
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe residue was purified by preparative TLC (EtOAc:MeC)H=100:3)

Sources & evidence

ORD record
ord-bcd9e630451b490dad9eba07a3e651ca
Source dataset
uspto-grants-2016_08
Patent number
US09415055B2

Reaction notes

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