Dimethylformamide → (2-{(E)-3-[1-(4-Bromo-benzenesulfonyl)-1H-pyrrol-3-yl]-allanoylamino}-phenyl)-carbamic acid tert-butyl ester

HRID 2408457Notes

Reaction equation

HRID 2408457 reaction equation
[Br: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.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:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=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 68524810(E)-3-[1-(4-Bromo-benzenesulfonyl)-1H-pyrrol-3-yl]acrylic acid

Product 1

HCID 86621696(2-{(E)-3-[1-(4-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 3.1 g (E)-3-[1-(4-bromo-benzenesulfonyl)-1H-pyrrol-3-yl]-acrylic acid with 170 ml DMF and 1.3 g HOBt.H2O and 12.0 ml triethylamine is stirred for 0.5 h. Then 4.9 g EDC.HCL is added and the suspension is stirred again at ambient temperature for 0.5 h. After that 1.8 g (2-amino-phenyl)-carbamic acid tert-butyl ester are added and the mixture 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.

Workup

  1. additionHCL is added
  2. stirringthe mixture 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-b45f6a8fdd5d430aaa2e62cb67757c29
Source dataset
uspto-grants-2014_08
Patent number
US08815855B2

Reaction notes

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