Methanol → N-(3-ethynyl-5-fluoro-4-methanesulfonylamino-benzyl)-3-(2-pyrrolidin-1-yl-6-trifluoromethyl-pyridin-3-yl)-propionamide

HRID 2266006Notes

Reaction equation

HRID 2266006 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:27]=[C:28]([F:35])[C:29]=1[NH:30][S:31]([CH3:34])(=[O:33])=[O:32])[CH2:6][NH:7][C:8](=[O:26])[CH:9]=[CH:10][C:11]1[C:12]([N:21]2[CH2:25][CH2:24][CH2:23][CH2:22]2)=[N:13][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:15][CH:16]=1)#[CH:2].CO>[Pd]>[C:1]([C:3]1[CH:4]=[C:5]([CH:27]=[C:28]([F:35])[C:29]=1[NH:30][S:31]([CH3:34])(=[O:32])=[O:33])[CH2:6][NH:7][C:8](=[O:26])[CH2:9][CH2:10][C:11]1[C:12]([N:21]2[CH2:22][CH2:23][CH2:24][CH2:25]2)=[N:13][C:14]([C:17]([F:18])([F:20])[F:19])=[CH:15][CH:16]=1)#[CH:2]

Participants

4

Reactant 2

HCID 887MethanolHCID 74382535N-(3-Ethynyl-5-fluoro-4-methanesulfonylamino-benzyl)-3-(2-pyrrolidin-1-yl-6-trifluoromethyl-pyridin-3-yl)-acrylamide

Product 1

HCID 59598267N-(3-ethynyl-5-fluoro-4-methanesulfonylamino-benzyl)-3-(2-pyrrolidin-1-yl-6-trifluoromethyl-pyridin-3-yl)-propionamideYield 100.9%

Reagents, catalysts & solvents 1

HCID 23938PalladiumSolvent

Procedure

To a suspension of N-(3-ethynyl-5-fluoro-4-methanesulfonylamino-benzyl)-3-(2-pyrrolidin-1-yl-6-trifluoromethyl-pyridin-3-yl)-acrylamide (15 mg, 0.029 mmol) in 5% Pd/C (5 mg) was added CH3OH (1.0 ml). The mixture was purged three times with hydrogen gas (50 psi) and then 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 N-(3-ethynyl-5-fluoro-4-methanesulfonylamino-benzyl)-3-(2-pyrrolidin-1-yl-6-trifluoromethyl-pyridin-3-yl)-propionamide (15 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-2b586abba1f645e5afcb657bcd6eba3b
Source dataset
uspto-grants-2010_12
Patent number
US07858621B2

Reaction notes

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