1,2-Dichloroethane → Tert-butyl 3-(isoquinolin-6-ylamino)-3-oxo-1-(thiophen-3-yl)propylcarbamate

HRID 509226Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 509226
[C:1]([O:5][C:6]([NH:8][CH:9]([C:14]1[CH:18]=[CH:17][S:16][CH:15]=1)[CH2:10][C:11]([OH:13])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(Cl)CCl.[NH2:23][C:24]1[CH:25]=[C:26]2[C:31](=[CH:32][CH:33]=1)[CH:30]=[N:29][CH:28]=[CH:27]2>N1C=CC=CC=1.CN(C1C=CN=CC=1)C>[CH:30]1[C:31]2[C:26](=[CH:25][C:24]([NH:23][C:11](=[O:13])[CH2:10][CH:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[C:14]3[CH:18]=[CH:17][S:16][CH:15]=3)=[CH:33][CH:32]=2)[CH:27]=[CH:28][N:29]=1

Komponenten

6

Edukt 3

HCID 111,2-DichloroethaneHCID 5889916-AminoisoquinolineHCID 27645363-((tert-Butoxycarbonyl)amino)-3-(thiophen-3-yl)propanoic acid

Produkt 1

HCID 59161737Tert-butyl 3-(isoquinolin-6-ylamino)-3-oxo-1-(thiophen-3-yl)propylcarbamate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 1049PyridineLösungsmittel

Versuchsvorschrift

To 3-(tert-butyoxcarbonylamino)-3-(thiophen-3-yl)propanoic acid (E4) in pyridine was added EDC, DMAP, and 6-aminoisoquinoline. The solution was stirred for 10 hours at room temperature. The mixture was poured into NaHCO3(sat) and extracted with EtOAc, dried (Na2SO4), filtered, and evaporated. Column chromatography (SiO2, 5% MeOH/CH2Cl2) gave pure tert-butyl 3-(isoquinolin-6-ylamino)-3-oxo-1-(thiophen-3-yl)propylcarbamate (E5).

Aufarbeitung

  1. extractionextracted with EtOAc
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-e15c828ca493423e9b92f97be109e45c
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09096569B2

Notizen zur Reaktion

Wird geladen…