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

HRID 2408456Notes

Reaction equation

HRID 2408456 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([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:5]=[CH:6][CH:7]=1.CN(C=O)C.C1C=CC2N(O)N=NC=2C=1.[O:36]1[CH2:41][CH2:40][CH2:39][CH2:38][CH:37]1[O:42][NH2:43]>C(Cl)CCl.C(N(CC)CC)C.O>[Br:1][C:2]1[CH:3]=[C:4]([S:8]([N:11]2[CH:15]=[CH:14][C:13](/[CH:16]=[CH:17]/[C:18]([NH:43][O:42][CH:37]3[CH2:38][CH2:39][CH2:40][CH2:41][O:36]3)=[O:20])=[CH:12]2)(=[O:9])=[O:10])[CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 757711-HydroxybenzotriazoleHCID 5142091O-(Tetrahydropyran-2-yl)hydroxylamineHCID 68526317(E)-3-[1-(3-bromo-benzenesulfonyl)-1H-pyrrol-3-yl]-acrylic acid

Product 1

HCID 86621698(E)-3-[1-(3-Bromo-benzenesulfonyl)-1H-pyrrol-3-yl]-N-(tetrahydro-pyran-2-yloxy)-acrylamide

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 962WaterSolventHCID 8471TriethylamineSolvent

Procedure

A mixture of 6.1 g (E)-3-[1-(3-bromo-benzenesulfonyl)-1H-pyrrol-3-yl]-acrylic acid with 300 ml DMF and 2.6 g HOBt.H2O and 24.0 ml triethylamine is stirred at ambient temperature for 0.5 h. Then 9.8 g EDC.HCL is added and the suspension is stirred again at ambient temperature for 0.5 h. After that 2.0 g O-(tetrahydro-2H-pyran-2-yl)hydroxylamine are added and the suspension is stirred at ambient temperature for 24 h. The DMF is evaporated and the residue is extracted with ethyl acetate and water. The organic layer is dried over sodium sulfate. The title compound is isolated by flash chromatography. By this method 6.3 g of a yellow foam are obtained.

Workup

  1. additionHCL is added
  2. stirringthe suspension is stirred at ambient temperature for 24 h
  3. customThe DMF is evaporated
  4. extractionthe residue is extracted with ethyl acetate and water
  5. dry with materialThe organic layer is dried over sodium sulfate

Sources & evidence

ORD record
ord-09a5b9688c974dbeab3f385b65cfce04
Source dataset
uspto-grants-2014_08
Patent number
US08815855B2

Reaction notes

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