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

HRID 1445504
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HRID 1445504 반응식
[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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 111,2-Dichloroethane용매
HCID 962Water용매
HCID 8471Triethylamine용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-0f7a19705c4841b9885736a9b8586c2f
출처 데이터셋
uspto-grants-2010_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07666868B2

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