Dimethylformamide → (2{(E)-3-[1-(3-Bromo-benzenesulfonyl)-1H-pyrrol-3-yl]-allanoylamino}-phenyl)-carbamic acid tert-butyl ester

HRID 2408455Notes

Reaction equation

HRID 2408455 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.[C:36]([O:40][C:41](=[O:50])[NH:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][C:44]=1[NH2:49])([CH3:39])([CH3:38])[CH3:37]>C(Cl)CCl.C(N(CC)CC)C.O>[C:36]([O:40][C:41](=[O:50])[NH:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][C:44]=1[NH:49][C:18](=[O:20])/[CH:17]=[CH:16]/[C:13]1[CH:14]=[CH:15][N:11]([S:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[CH:3]=2)(=[O:9])=[O:10])[CH:12]=1)([CH3:39])([CH3:37])[CH3:38]

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 757711-HydroxybenzotriazoleHCID 676311N-(tert-Butoxycarbonyl)-1,2-phenylenediamineHCID 68526317(E)-3-[1-(3-bromo-benzenesulfonyl)-1H-pyrrol-3-yl]-acrylic acid

Product 1

HCID 86621709(2{(E)-3-[1-(3-Bromo-benzenesulfonyl)-1H-pyrrol-3-yl]-allanoylamino}-phenyl)-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 962WaterSolventHCID 8471TriethylamineSolvent

Procedure

A mixture of 5.4 g (E)-3-[1-(3-bromo-benzenesulfonyl)-1H-pyrrol-3-yl]-acrylic acid with 300 ml DMF and 2.34 g HOBt.H2O and 21.0 ml Triethylamine is stirred at ambient temperature for 0.5 h. Then it is added 8.8 g EDC.HCL and it is stirred again at ambient temperature for 0.5 h. Finally 3.2 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. The title product is isolated by flash chromatography. By this method 6.3 g of a yellow foam is obtained.

Workup

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

Sources & evidence

ORD record
ord-31b3a8a2e9ce4a21ad2105cf3783a08e
Source dataset
uspto-grants-2014_08
Patent number
US08815855B2

Reaction notes

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