Dimethylformamide → (E)-[1-(4-Bromo-benzenesulfonyl)-1H-pyrrol-3-yl]-(tetrahydro-pyran-2-yloxy)-acrylamide

HRID 1445501Notes

Reaction equation

HRID 1445501 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[CH:15]=[CH:14][C:13](/[CH:16]=[CH:17]/[C:18]([OH:20])=O)=[CH:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.C[N:22](C=O)C.[O:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH:27]1[O:32]N>CCN(CC)CC>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([N:11]2[CH:15]=[CH:14][C:13](/[CH:16]=[C:17](/[O:32][CH:27]3[CH2:28][CH2:29][CH2:30][CH2:31][O:26]3)\[C:18]([NH2:22])=[O:20])=[CH:12]2)(=[O:9])=[O:10])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 5142091O-(Tetrahydropyran-2-yl)hydroxylamineHCID 68524810(E)-3-[1-(4-Bromo-benzenesulfonyl)-1H-pyrrol-3-yl]acrylic acid

Product 1

HCID 86621707(E)-[1-(4-Bromo-benzenesulfonyl)-1H-pyrrol-3-yl]-(tetrahydro-pyran-2-yloxy)-acrylamide

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a mixture of 3.16 g (E)-3-[1-(4-Bromo-benzenesulfonyl)-1H-pyrrol-3-yl]-acrylic acid and 170 ml DMF are added 1.06 g HOBtxH2O and 7.02 g Et3N. This mixture is stirred for 70 min at ambient temperature. 3.99 g EDCxHCl are added and the reaction mixture is stirred for additional 45 min. 0.812 g O-(tetrahydro-2H-pyran-2-yl)-hydroxylamin are added and the reaction mixture is stirred overnight. The solvent is evaporated and the residue is partitioned between ethyl acetate and water. The organic phase is dried, evaporated and the crude product is purified by silica gel flash chromatography.

Workup

  1. addition3.99 g EDCxHCl are added
  2. stirringthe reaction mixture is stirred for additional 45 min
  3. stirringthe reaction mixture is stirred overnight
  4. customThe solvent is evaporated
  5. customthe residue is partitioned between ethyl acetate and water
  6. customThe organic phase is dried
  7. customevaporated
  8. customthe crude product is purified by silica gel flash chromatography

Sources & evidence

ORD record
ord-3d3b5d0757364e749d4a9278cd5e760e
Source dataset
uspto-grants-2010_02
Patent number
US07666868B2

Reaction notes

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