2-Methoxyethylamine → HCID 68784905, compound

HRID 2265970Notes

Reaction equation

HRID 2265970 reaction equation
Cl[C:2]1[C:7]([CH:8]=[CH:9][C:10]([NH:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([NH:20][S:21]([CH3:24])(=[O:23])=[O:22])=[C:16]([F:25])[CH:15]=2)=[O:11])=[CH:6][CH:5]=[C:4]([C:26]([F:29])([F:28])[F:27])[N:3]=1.[CH3:30][O:31][CH2:32][CH2:33][NH2:34].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.CCOC(C)=O>[F:25][C:16]1[CH:15]=[C:14]([CH:19]=[CH:18][C:17]=1[NH:20][S:21]([CH3:24])(=[O:23])=[O:22])[CH2:13][NH:12][C:10](=[O:11])[CH:9]=[CH:8][C:7]1[C:2]([NH:34][CH2:33][CH2:32][O:31][CH3:30])=[N:3][C:4]([C:26]([F:29])([F:28])[F:27])=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 80182-MethoxyethylamineHCID 11430Potassium CarbonateHCID 723356643-(2-chloro-6-trifluoromethyl-pyridin-3-yl)-N-(3-fluoro-4-methanesulfonylamino-benzyl)-acrylamide

Product 1

HCID 68784905HCID 68784905, compoundYield 26%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

To a suspension of 3-(2-chloro-6-trifluoromethyl-pyridin-3-yl)-N-(3-fluoro-4-methanesulfonylamino-benzyl)-acrylamide (35 mg, 0.077 mmol) and methoxyethylamine (5 eq) in DMF (0.5 ml) was added K2CO3 (5 eq). The mixture was stirred for 12 hours at 110° C. The reaction mixture was diluted with EtOAc and then washed two times with 1N-HCl and brine, dried over MgSO4, filtered and concentrated under reduced pressure. The crude residue was column-chromatographed to yield the title compound (10 mg, 26%).

Workup

  1. washwashed two times with 1N-HCl and brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude residue was column-chromatographed

Sources & evidence

ORD record
ord-4835714fd7a44e838c8a44e0ce2bd7f5
Source dataset
uspto-grants-2010_12
Patent number
US07858621B2

Reaction notes

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