Dimethylformamide → HCID 86762611, compound

HRID 2408454Notes

Reaction equation

HRID 2408454 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.[C:25]([O:29][C:30](=[O:39])[NH:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[NH2:38])([CH3:28])([CH3:27])[CH3:26]>C(N(CC)CC)C>[C:25]([O:29][C:30](=[O:39])[NH:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[NH:38][C:17](=[O:19])/[CH:16]=[CH:15]/[C:12]1[CH:13]=[CH:14][N:10]([S:7]([C:5]2[S:6][C:2]([Br:1])=[CH:3][CH:4]=2)(=[O:8])=[O:9])[CH:11]=1)([CH3:28])([CH3:26])[CH3:27]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 676311N-(tert-Butoxycarbonyl)-1,2-phenylenediamineHCID 68525252HCID 68525252, compound

Product 1

HCID 86762611HCID 86762611, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A mixture of 4.1 g (E)-3-[1-(5-bromo-thiophene-2-sulfonyl)-1H-pyrrol-3-yl]-acrylic acid with 200 ml DMF and 1.8 g HOBtxH2O and 16.0 ml triethylamine is stirred for 0.5 h. Then it is added 6.6 g EDCxHCL and stirred for 0.5 h. After that 2.4 g (2-amino-phenyl)-carbamic acid tert-butyl ester 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 3.7 g of a colorless solid is obtained.

Workup

  1. additionThen it is added 6.6 g EDCxHCL
  2. stirringstirred 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-7a474aed75a0426cb8f63fbdd91c8825
Source dataset
uspto-grants-2014_08
Patent number
US08815855B2

Reaction notes

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