Methyl morpholine oxide → HCID 73672704, compound

HRID 514969Notes

Reaction equation

HRID 514969 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 stirred 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:MeOH=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. 1HNMR (CDCl3 400 MHz): δ8.59 (s, 2H), 7.56 (dd, J=8.0 Hz, 1.6 Hz, 1H), 7.49 (dd, J=7.6 Hz, 1.6 Hz, 1H), 7.34-7.27 (m, 1H), 6.63 (br, 1H), 4.08-3.82 (m, 3H), 2.95-2.82 (m, 2H), 2.79-2.65 (m, 5H), 2.55-2.40 (m, 4H). LCMS (MH+): m/z=425.0, tR (minutes, Method F)=1.75

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:MeOH=100:3)

Sources & evidence

ORD record
ord-f8e9e37aa14940beaf9d9170b85d444e
Source dataset
uspto-grants-2015_08
Patent number
US09108938B2

Reaction notes

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