3-(2-Chloro-6-trifluoromethyl-pyridin-3-yl)-N-(3-ethynyl-5-fluoro-4-methanesulfonylamino-benzyl)-acrylamide → N-(3-Ethynyl-5-fluoro-4-methanesulfonylamino-benzyl)-3-(2-methoxy-6-trifluoromethyl-pyridin-3-yl)-acrylamide

HRID 2265967Notes

Reaction equation

HRID 2265967 reaction equation
Cl[C:2]1[C:7]([CH:8]=[CH:9][C:10]([NH:12][CH2:13][C:14]2[CH:19]=[C:18]([F:20])[C:17]([NH:21][S:22]([CH3:25])(=[O:24])=[O:23])=[C:16]([C:26]#[CH:27])[CH:15]=2)=[O:11])=[CH:6][CH:5]=[C:4]([C:28]([F:31])([F:30])[F:29])[N:3]=1.[O:32]([CH3:34])[Na]>CO.CCOC(C)=O>[C:26]([C:16]1[CH:15]=[C:14]([CH:19]=[C:18]([F:20])[C:17]=1[NH:21][S:22]([CH3:25])(=[O:24])=[O:23])[CH2:13][NH:12][C:10](=[O:11])[CH:9]=[CH:8][C:7]1[C:2]([O:32][CH3:34])=[N:3][C:4]([C:28]([F:31])([F:30])[F:29])=[CH:5][CH:6]=1)#[CH:27]

Participants

5

Reactant 2

HCID 743823853-(2-Chloro-6-trifluoromethyl-pyridin-3-yl)-N-(3-ethynyl-5-fluoro-4-methanesulfonylamino-benzyl)-acrylamideHCID 178418582HCID 178418582, compound

Product 1

HCID 74382457N-(3-Ethynyl-5-fluoro-4-methanesulfonylamino-benzyl)-3-(2-methoxy-6-trifluoromethyl-pyridin-3-yl)-acrylamideYield 20%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 3-(2-chloro-6-trifluoromethyl-pyridin-3-yl)-N-(3-ethynyl-5-fluoro-4-methanesulfonylamino-benzyl)-acrylamide (50 mg, 0.105 mmol) in CH3OH (1 mL) was added dropwise 30% NaOCH3 in CH3OH (3 eq) at 0° C. The mixture was stirred for 12 hours at room temperature. The reaction was diluted with EtOAc and washed two times with 1N HCl and brine, dried over anhyd. MgSO4, filtered and concentrated under reduced pressure. The resulting residue was purified by column chromatography to give the title compound (10 mg, 20%).

Workup

  1. washwashed two times with 1N HCl and brine
  2. customdried over anhyd
  3. filtrationMgSO4, filtered
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by column chromatography

Sources & evidence

ORD record
ord-70f024a6ff0e45338243495895479039
Source dataset
uspto-grants-2010_12
Patent number
US07858621B2

Reaction notes

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