Methanol → 3-(2-butoxy-6-trifluoromethyl-pyridin-3-yl)-N-(3-fluoro-4-methanesulfonylamino-benzyl)-propionamide

HRID 2266005Notes

Reaction equation

HRID 2266005 reaction equation
[CH2:1]([O:5][C:6]1[C:11]([CH:12]=[CH:13][C:14]([NH:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([NH:24][S:25]([CH3:28])(=[O:27])=[O:26])=[C:20]([F:29])[CH:19]=2)=[O:15])=[CH:10][CH:9]=[C:8]([C:30]([F:33])([F:32])[F:31])[N:7]=1)[CH2:2][CH2:3][CH3:4].CO>[Pd]>[CH2:1]([O:5][C:6]1[C:11]([CH2:12][CH2:13][C:14]([NH:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([NH:24][S:25]([CH3:28])(=[O:26])=[O:27])=[C:20]([F:29])[CH:19]=2)=[O:15])=[CH:10][CH:9]=[C:8]([C:30]([F:32])([F:33])[F:31])[N:7]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 887MethanolHCID 687828593-(2-butoxy-6-trifluoromethyl-pyridin-3-yl)-N-(3-fluoro-4-methanesulfonylamino-benzyl)-acrylamide

Product 1

HCID 595982853-(2-butoxy-6-trifluoromethyl-pyridin-3-yl)-N-(3-fluoro-4-methanesulfonylamino-benzyl)-propionamideYield 99.1%

Reagents, catalysts & solvents 1

HCID 23938PalladiumSolvent

Procedure

To a suspension of 3-(2-butoxy-6-trifluoromethyl-pyridin-3-yl)-N-(3-fluoro-4-methanesulfonylamino-benzyl)-acrylamide (19.3 mg, 0.039 mmol) in 5% Pd/C (6 mg) was added CH3OH (1.0 ml). The mixture was purged three times with hydrogen gas (50 psi) and shaken for 40 min at room temperature. The reaction mixture was filtered over celite pad and concentrated under reduced pressure. The crude residue was chromatographed to yield the 3-(2-butoxy-6-trifluoromethyl-pyridin-3-yl)-N-(3-fluoro-4-methanesulfonylamino-benzyl)-propionamide (19 mg, 98%).

Workup

  1. customThe mixture was purged three times with hydrogen gas (50 psi)
  2. filtrationThe reaction mixture was filtered over celite pad
  3. concentrationconcentrated under reduced pressure
  4. customThe crude residue was chromatographed

Sources & evidence

ORD record
ord-38689f52bc79432fa5716a884aa8f122
Source dataset
uspto-grants-2010_12
Patent number
US07858621B2

Reaction notes

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