1,2-Dichloroethane → (E)-3-(6-aminopyridin-3-yl)-N-(1,4-dimethyl-1H-indole-3-ylmethyl)-N-methylacrylamide

HRID 1690402Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1690402
[CH3:1][N:2]1[C:10]2[C:5](=[C:6]([CH3:11])[CH:7]=[CH:8][CH:9]=2)[C:4]([CH2:12][NH:13][CH3:14])=[CH:3]1.[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.C1C=CC2N(O)N=NC=2C=1.O.C(Cl)CCl>CN(C=O)C.CCN(CC)CC>[NH2:15][C:16]1[N:21]=[CH:20][C:19](/[CH:22]=[CH:23]/[C:24]([N:13]([CH2:12][C:4]2[C:5]3[C:10](=[CH:9][CH:8]=[CH:7][C:6]=3[CH3:11])[N:2]([CH3:1])[CH:3]=2)[CH3:14])=[O:26])=[CH:18][CH:17]=1

Komponenten

8

Edukt 5

HCID 111,2-DichloroethaneHCID 962WaterHCID 757711-HydroxybenzotriazoleHCID 10487224(2E)-3-(6-aminopyridin-3-yl)prop-2-enoic acidHCID 221390221,4-dimethyl-3-(methylaminomethyl)-1H-indole

Produkt 1

HCID 10088258(E)-3-(6-aminopyridin-3-yl)-N-(1,4-dimethyl-1H-indole-3-ylmethyl)-N-methylacrylamideAusbeute 36 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

To a stirred solution of 1,4-dimethyl-3-(methylaminomethyl)-1H-indole (188.2 mg, 1 mmole) and (E)-3-(6-aminopyridin-3-yl)acrylic acid (164 mg, 1 mmole) in dry DMF (12 mL) containing dry Et3N (4 mL) was added HOBt.H2O (153 mg, 1 mmole) and EDC (191.8 mg, 1 mmole). The reaction was stirred overnight under argon at ambient temperature, then was concentrated in vacuo. The residue was partitioned between EtOAc and 5% NaHCO3 solution, and the layers were separated. The organic layer was washed with brine, dried (MgSO4), filtered, and concentrated. Flash chromatography on silica gel afforded the title compound (120 mg, 36%) as a white solid: MS (ES) m/e 335.2 (M+H)+.

Aufarbeitung

  1. concentrationwas concentrated in vacuo
  2. customThe residue was partitioned between EtOAc and 5% NaHCO3 solution
  3. customthe layers were separated
  4. washThe organic layer was washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-846eee9694cb45638a53285bb20d70d2
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08153652B2

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