2-(2-Aminoethyl)-1-methylpyrrolidine → 6-(3,4-Dichlorophenyl)-2-(2-(1-methylpyrrolidin-2-yl)ethylamino)-5,6-dihydrobenzo[f]isoquinoline-1-carbonitrile

HRID 1808034

Reaktionsgleichung

Reaktionsgleichung von HRID 1808034
Cl[C:2]1[C:11]([C:12]#[N:13])=[C:10]2[C:5]([CH2:6][CH:7]([C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([Cl:25])[CH:19]=3)[C:8]3[CH:17]=[CH:16][CH:15]=[CH:14][C:9]=32)=[CH:4][N:3]=1.[CH3:26][N:27]1[CH2:31][CH2:30][CH2:29][CH:28]1[CH2:32][CH2:33][NH2:34]>CN(C)C=O>[Cl:25][C:20]1[CH:19]=[C:18]([CH:7]2[CH2:6][C:5]3[C:10](=[C:11]([C:12]#[N:13])[C:2]([NH:34][CH2:33][CH2:32][CH:28]4[CH2:29][CH2:30][CH2:31][N:27]4[CH3:26])=[N:3][CH:4]=3)[C:9]3[CH:14]=[CH:15][CH:16]=[CH:17][C:8]2=3)[CH:23]=[CH:22][C:21]=1[Cl:24]

Komponenten

4

Edukt 2

HCID 983882-(2-Aminoethyl)-1-methylpyrrolidineHCID 866455862-Chloro-6-(3,4-dichlorophenyl)-5,6-dihydrobenzo[f]isoquinoline-1-carbonitrile

Produkt 1

HCID 674274526-(3,4-Dichlorophenyl)-2-(2-(1-methylpyrrolidin-2-yl)ethylamino)-5,6-dihydrobenzo[f]isoquinoline-1-carbonitrileAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 2-chloro-6-(3,4-dichlorophenyl)-5,6-dihydrobenzo[f]isoquinoline-1-carbonitrile (156 mg, 0.405 mmol) in N,N-dimethylformamide (3.5 ml) and 2-(1-methylpyrrolidin-2-yl)ethanamine (250 ul) was heated under microwave conditions at 20° C. for 40 minutes. The mixture was partitioned between ethyl acetate (50 ml) and water (30 ml). The aqueous layer was removed and the organic layer was washed with water (3×30 ml) and dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by flash column chromatography on silica gel using a gradient of dichloromethane-methanol as eluent to afford 6-(3,4-dichlorophenyl)-2-(2-(1-methylpyrrolidin-2-yl)ethylamino)-5,6-dihydrobenzo[f]isoquinoline-1-carbonitrile as a yellow solid (96 mg, 50%). M.p.=131-134° C. 400 MHz 1H NMR (DMSO-d6) δ 8.30 (m, 1H), 8.14 (s, 1H), 7.49 (m, 5H), 7.13 (m, 1H), 7.00 (dd, J=8 and 2 Hz, 1H), 4.30 (m, 1H), 3.43 (m, 2H), 3.08 (dd, J=15.2 and 7.2 Hz, 1H), 2.92 (dd, J=15.2 and 5.6 Hz, 1H), 2.37 (m, 6H), 1.97 (m, 1H), 1.89 (m, 1H), 1.68 (m, 3H), 1.55 (m, 1H). LCMS m/e 477 [M+H].

Aufarbeitung

  1. customThe mixture was partitioned between ethyl acetate (50 ml) and water (30 ml)
  2. customThe aqueous layer was removed
  3. washthe organic layer was washed with water (3×30 ml)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by flash column chromatography on silica gel using a gradient of dichloromethane-methanol as eluent

Quellen und Nachweise

ORD-Eintrag
ord-281aa85754b44a35815d947600df1c58
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08357694B2

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