Pyrrolidine → N-(3-Fluoro-4-methanesulfonylamino-benzyl)-3-(6-pyrrolidin-1-yl-pyridin-3-yl)-acrylamide

HRID 2265941Notes

Reaction equation

HRID 2265941 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([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:4][CH:3]=1.[NH:26]1[CH2:30][CH2:29][CH2:28][CH2:27]1>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:5]1[CH:6]=[N:7][C:2]([N:26]2[CH2:30][CH2:29][CH2:28][CH2:27]2)=[CH:3][CH:4]=1

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 723356623-(6-Chloro-pyridin-3-yl)-N-(3-fluoro-4-methane sulfonylamino-benzyl)-acrylamide

Product 1

HCID 68786118N-(3-Fluoro-4-methanesulfonylamino-benzyl)-3-(6-pyrrolidin-1-yl-pyridin-3-yl)-acrylamideYield 24%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

3-(6-Chloro-pyridin-3-yl)-N-(3-fluoro-4-methanesulfonylamino-benzyl)-acrylamide (15 mg, 0.413 mmol) was added to pyrrolidine (0.5 ml) and the mixture was stirred for 12 hrs at 90° C. The resulting residue was dissolved in EtOAc, then washed three times with H2O, and neutralized with 1N HCl to pH 5˜7. The resulting solution was washed with brine, and then dried over anhyd. Na2SO4, filtered and concentrated under reduced pressure. The crude residue was recrystallized (CH2Cl2) to yield the title compound (4 mg, 24%).

Workup

  1. washwashed three times with H2O
  2. washThe resulting solution was washed with brine
  3. customdried over anhyd
  4. filtrationNa2SO4, filtered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude residue was recrystallized (CH2Cl2)

Sources & evidence

ORD record
ord-c429ffac958c4486b81e7f98f8ac81f1
Source dataset
uspto-grants-2010_12
Patent number
US07858621B2

Reaction notes

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