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

HRID 1445501
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HRID 1445501 반응식
[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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8471Triethylamine용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-3d3b5d0757364e749d4a9278cd5e760e
출처 데이터셋
uspto-grants-2010_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07666868B2

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