1,2-Dichloroethane → (E)-3-[6-[N-(methoxycarbonylmethyl)amino]pyridin-3-yl]-N-methyl-N-(2-methyl-1H-indol-3-ylmethyl)acrylamide

HRID 1690395Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1690395
Cl.[CH3:2][O:3][C:4]([CH2:6][NH:7][C:8]1[N:13]=[CH:12][C:11](/[CH:14]=[CH:15]/[C:16]([OH:18])=O)=[CH:10][CH:9]=1)=[O:5].[CH3:19][C:20]1[NH:21][C:22]2[C:27]([C:28]=1[CH2:29][NH:30][CH3:31])=[CH:26][CH:25]=[CH:24][CH:23]=2.CCN(CC)CC.C1C=CC2N(O)N=NC=2C=1.O.C(Cl)CCl>CN(C=O)C.C(Cl)Cl>[CH3:2][O:3][C:4]([CH2:6][NH:7][C:8]1[N:13]=[CH:12][C:11](/[CH:14]=[CH:15]/[C:16]([N:30]([CH3:31])[CH2:29][C:28]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[NH:21][C:20]=2[CH3:19])=[O:18])=[CH:10][CH:9]=1)=[O:5]

Komponenten

8

Edukt 6

HCID 111,2-DichloroethaneHCID 962WaterHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 10954023N-Methyl-N-[(2-methyl-1H-indol-3-yl)methyl]amineHCID 66905135(e)-3-[6-[n-(Methoxycarbonylmethyl)amino]pyridin-3-yl]acrylic acid hydrochloride salt

Produkt 1

HCID 10363109(E)-3-[6-[N-(methoxycarbonylmethyl)amino]pyridin-3-yl]-N-methyl-N-(2-methyl-1H-indol-3-ylmethyl)acrylamideAusbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 22350042dichloromethane N,N-dimethylformamideLösungsmittel

Versuchsvorschrift

To a stirred solution of (E)-3-[6-[N-(methoxycarbonylmethyl)amino]pyridin-3-yl]acrylic acid hydrochloride salt (2.0 g, 7.3 mmole) in 1:1 DMF/CH2Cl2 (100 mL) was added 2-methyl-3-(methylaminomethyl)indole (1.3 g, 7.5 mmole), Et3N (2.1 mL, 15 mmole), and HOBt.H2O (1.0 g, 7.4 mmole), followed by EDC (1.4 g, 7.3 mmole). After stirring at room temperature for 18 h the reaction was concentrated to dryness. The residue was taken up in EtOAc, and the solution was washed with H2O then brine, dried (Na2SO4), and concentrated under vacuum. The remaining residue was purified by flash chromatography on silica gel (4% MeOH/CHCl3) to give the title compound (2.08 g, 73%) as an off-white solid: MS (ES) m/e 393.2 (M+H)+.

Aufarbeitung

  1. concentrationwas concentrated to dryness
  2. washthe solution was washed with H2O
  3. dry with materialbrine, dried (Na2SO4)
  4. concentrationconcentrated under vacuum
  5. customThe remaining residue was purified by flash chromatography on silica gel (4% MeOH/CHCl3)

Quellen und Nachweise

ORD-Eintrag
ord-38daae0dd7ae48f4a42dfdbb2a2a5713
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08153652B2

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