HCID 89544968, compound → HCID 89544821, compound

HRID 2283445Notes

Reaction equation

HRID 2283445 reaction equation
[Cl:1][C:2]1[C:7]([CH:8]([C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)[OH:9])=[C:6]([F:16])[C:5]([C@H:17]([NH:20][CH3:21])[CH2:18][CH3:19])=[CH:4][CH:3]=1>C1(C)C=CC=CC=1.ClCCCl.[O-2].[Mn+4].[O-2]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C@H:17]([NH:20][CH3:21])[CH2:18][CH3:19])=[C:6]([F:16])[C:7]=1[C:8]([C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1)=[O:9]

Participants

5

Reactant 1

HCID 89544968HCID 89544968, compound

Product 1

HCID 89544821HCID 89544821, compound

Reagents, catalysts & solvents 3

HCID 178418406HCID 178418406, compoundCatalystHCID 111,2-DichloroethaneSolventHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

Step 3 A stirred suspension of {6-chloro-2-fluoro-3-[(1R)-1-(methylamino)propyl]-phenyl}(pyridin-3-yl)methanol (0.123 g, 0.398 mmol) and manganese(IV) oxide (0.693 g, 7.97 mmol) in toluene (1.99 mL) and 1,2-dichloroethane (1.99 mL) was heated at 100° C. for 2.5 hours. Upon cooling, the mixture was filtered; the residual solids were washed with DCM (×2) and concentrated. Preparative HPLC gave [(1R)-1-{4-chloro-2-fluoro-3-[(pyridin-3-yl)carbonyl]phenyl}propyl](methyl)amine which was converted to the HCl salt, 0.012 g, 9%.

Workup

  1. temperatureUpon cooling
  2. filtrationthe mixture was filtered
  3. washthe residual solids were washed with DCM (×2)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-df9713624c984f118dc5b63215350078
Source dataset
uspto-grants-2015_09
Patent number
US09145354B2

Reaction notes

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