Triethylamine → HCID 86621693, compound

HRID 2408453Notes

Reaction equation

HRID 2408453 reaction equation
[I: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.CCN(CC)CC.[C:28]([NH:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=1[NH2:42])([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29]>CN(C=O)C>[C:31]([O:30][C:28](=[O:29])[NH:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=1[NH:42][C:18](=[O:20])/[CH:17]=[CH:16]/[C:13]1[CH:14]=[CH:15][N:11]([S:8]([C:5]2[CH:4]=[CH:3][C:2]([I:1])=[CH:7][CH:6]=2)(=[O:9])=[O:10])[CH:12]=1)([CH3:34])([CH3:32])[CH3:33]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 676311N-(tert-Butoxycarbonyl)-1,2-phenylenediamineHCID 68526678HCID 68526678, compound

Product 1

HCID 86621693HCID 86621693, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2.5 g (E)-3-[1-(4-Iodo-benzenesulfonyl)-1H-pyrrol-3-yl]-acrylic acid is dissolved in 140 ml DMF. To this mixture are added 0.949 g HOBtxH2O, and 6.27 g Et3N. After 30 min 3.57 g EDCxHCl are added and the resulting mixture is stirred for 30 min. Now 1.29 g of N-boc-o-phenylenediamine 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 and evaporated and the crude product is purified by silica gel flash chromatography.

Workup

  1. additionAfter 30 min 3.57 g EDCxHCl are added
  2. stirringthe reaction mixture is stirred overnight
  3. customThe solvent is evaporated
  4. customthe residue is partitioned between ethyl acetate and water
  5. customThe organic phase is dried
  6. customevaporated
  7. customthe crude product is purified by silica gel flash chromatography

Sources & evidence

ORD record
ord-13c5cc0f36834449ad57725f78cb001a
Source dataset
uspto-grants-2014_08
Patent number
US08815855B2

Reaction notes

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