Hydrochloric Acid → HCID 136340674, Verbindung

HRID 69391Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 69391
[CH3:1][N:2]([CH3:37])[CH2:3][CH2:4][N:5]1[C:13](=[O:14])[C:12]2[CH:11]=[C:10]3[NH:15][C:16]([C:18]4[C:19]([O:34]C)=[N:20][CH:21]=[CH:22][C:23]=4[O:24][CH:25]([CH3:33])[CH2:26][C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)=[N:17][C:9]3=[CH:8][C:7]=2[C:6]1=[O:36].Cl>O1CCOCC1>[CH3:37][N:2]([CH3:1])[CH2:3][CH2:4][N:5]1[C:13](=[O:14])[C:12]2[CH:11]=[C:10]3[NH:15][C:16]([C:18]4[C:19](=[O:34])[NH:20][CH:21]=[CH:22][C:23]=4[O:24][CH:25]([CH3:33])[CH2:26][C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)=[N:17][C:9]3=[CH:8][C:7]=2[C:6]1=[O:36]

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 666906826-(2-(Dimethylamino)ethyl)-2-(2-methoxy-4-((1-phenylpropan-2-yl)oxy)pyridine-3-yl)imidazo[4,5-f]isoindole-5,7(1H,6H)-dione

Produkt 1

HCID 136340674HCID 136340674, VerbindungAusbeute 75,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

6-(2-(Dimethylamino)ethyl)-2-(2-methoxy-4-((1-phenylpropan-2-yl)oxy)pyridine-3-yl)imidazo[4,5-f]isoindole-5,7(1H,6H)-dione (0.52 g, 1.04 mmol) was dissolved in 30 mL of 1,4-dioxane at rt. 5 mL of concentrated HCl was added. The reaction mixture was stirred at rt for 12 h. The volatile was removed under reduced pressure. The residue was washed with 20 mL of saturated K2CO3 solution. The pale-yellow precipitate was purified by column chromatography (silica-gel, CH2Cl2/MeOH=7/3 v/v) to give a pale-yellow solid product, 0.38 g, 75.2% yield. MS: 486.8 [M+H]+. 1H-NMR (DMSO-d6, 500 MHz): δ 13.24 (s, 1H), 11.98 (s, 1H), 8.03 (s, 2H), 7.60 (d, 1H, J=7.0 Hz), 7.34-7.32 (m, 2H), 7.12-7.09 (m, 3H), 6.46 (d, 1H, J=7.5 Hz), 4.93-4.87 (m, 1H), 3.70 (t, 2H, J=7.0 Hz), 3.03-2.91 (m, 2H), 2.52 (t, 2H, J=7.0 Hz), 2.19 (s, 6H), 1.27 (d, 3H, J=6.0 Hz).

Aufarbeitung

  1. customThe volatile was removed under reduced pressure
  2. washThe residue was washed with 20 mL of saturated K2CO3 solution
  3. customThe pale-yellow precipitate was purified by column chromatography (silica-gel, CH2Cl2/MeOH=7/3 v/v)
  4. customto give a pale-yellow solid product, 0.38 g, 75.2% yield

Quellen und Nachweise

ORD-Eintrag
ord-9968df33e3014a8bbfe8497a413e1aa1
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822500B2

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