1,2-Dichloroethane → (E)-3-(6-aminopyridin-3-yl)-N-(1,2-dimethyl-1H-indol-3-ylmethyl)-N-methylacrylamide

HRID 1761131

Reaktionsgleichung

Reaktionsgleichung von HRID 1761131
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH2:11][NH:12][CH3:13])=[C:3]1[CH3:14].[NH2:15][C:16]1[N:21]=[CH:20][C:19](/[CH:22]=[CH:23]/[C:24]([OH:26])=O)=[CH:18][CH:17]=1.CCN(CC)CC.C1C=CC2N(O)N=NC=2C=1.O.C(Cl)CCl>CN(C=O)C.C(C1CCCCC1)C1CCCCC1>[NH2:15][C:16]1[N:21]=[CH:20][C:19](/[CH:22]=[CH:23]/[C:24]([N:12]([CH2:11][C:4]2[C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[N:2]([CH3:1])[C:3]=2[CH3:14])[CH3:13])=[O:26])=[CH:18][CH:17]=1

Komponenten

7

Edukt 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 27960291-Hydroxybenzotriazole hydrateHCID 10487224(2E)-3-(6-aminopyridin-3-yl)prop-2-enoic acidHCID 10877907[(1,2-dimethyl-1H-indol-3-yl)methyl](methyl)amine

Produkt 1

HCID 60208937(E)-3-(6-aminopyridin-3-yl)-N-(1,2-dimethyl-1H-indol-3-ylmethyl)-N-methylacrylamideAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 131724718DMF CH2Cy2Lösungsmittel

Versuchsvorschrift

To a stirred solution of 1,2-dimethyl-3-(methylaminomethyl)-1H-indol e (0.8 g, 4.2 mmole) in 1:1 DMF/CH2Cy2 (30 mL) at RT was added (E)-3-(6-aminopyridin-3-yl)acrylic acid (0.7 g, 4.3 mmole), Et3N (0.61 ml, 4.3 mmole), HOBt H2O (0.58 g, 4.3 mmole) and EDC (0.83 g, 4.3 mmole). After 16 h the reaction was concentrated under vacuum and the residue was taken up in EtOAc (100 mL). The solution was washed with 1.0 N Na2CO3 (100 mL) then with brine, dried (Na2SO4), and concentrated. Purification by flas h chromatography on silica gel (4% MeOv.CHCl3) followed by trituration with 1:1 Et2O/petroleum ether and drying under vacuum gave (he title compound (1.36 g, 97%) as an off-white solid: MS (ES) H+e 335.2 (M+H)+.

Aufarbeitung

  1. concentrationAfter 16 h the reaction was concentrated under vacuum
  2. washThe solution was washed with 1.0 N Na2CO3 (100 mL)
  3. dry with materialwith brine, dried (Na2SO4)
  4. concentrationconcentrated
  5. customPurification
  6. customdrying under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-266dcd67d21e4d468ccf4b4607f45db9
Quelldatensatz
uspto-grants-2005_01
Patentnummer
US06846819B1

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