Dimethylformamide → HCID 86621708, compound

HRID 1445503Notes

Reaction equation

HRID 1445503 reaction equation
[Br:1][C:2]1[S:6][C:5]([S:7]([N:10]2[CH:14]=[CH:13][C:12](/[CH:15]=[CH:16]/[C:17]([OH:19])=O)=[CH:11]2)(=[O:9])=[O:8])=[CH:4][CH:3]=1.CN(C=O)C.[O:25]1[CH2:30][CH2:29][CH2:28][CH2:27][CH:26]1[O:31][NH2:32]>C(N(CC)CC)C>[Br:1][C:2]1[S:6][C:5]([S:7]([N:10]2[CH:14]=[CH:13][C:12](/[CH:15]=[CH:16]/[C:17]([NH:32][O:31][CH:26]3[CH2:27][CH2:28][CH2:29][CH2:30][O:25]3)=[O:19])=[CH:11]2)(=[O:8])=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 5142091O-(Tetrahydropyran-2-yl)hydroxylamineHCID 68525252HCID 68525252, compound

Product 1

HCID 86621708HCID 86621708, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A mixture of 3.8 g (E)-3-[1-(5-bromo-thiophene-2-sulfonyl)-1H-pyrrol-3-yl]-acrylic acid with 200 ml DMF and 1.6 g HOBtxH2O and 15.0 ml triethylamine is stirred at ambient temperature for 0.5 h. Then 6.04 g EDCxHCL are added and the suspension is stirred again for 0.5 h. Finally 1.23 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 and evaporated. The title product is isolated by flash chromatography. By this method 4.6 g of a yellow foam are obtained.

Workup

  1. additionThen 6.04 g EDCxHCL are added
  2. stirringthe suspension is stirred again for 0.5 h
  3. stirringthe suspension is stirred at ambient temperature for 24 h
  4. customThe DMF is evaporated
  5. extractionthe residue is extracted with ethyl acetate and water
  6. dry with materialThe organic layer is dried over sodium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-1abe8faabd9e4ab581d14e75014f22f7
Source dataset
uspto-grants-2010_02
Patent number
US07666868B2

Reaction notes

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