5,6-Diamino-2-(2-(dimethylamino)ethyl)isoindoline-1,3-dione → 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

HRID 920518Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 920518
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[NH2:11])[C:7](=[O:12])[N:6]([CH2:13][CH2:14][N:15]([CH3:17])[CH3:16])[C:5]2=[O:18].[CH3:19][O:20][C:21]1[N:28]=[CH:27][CH:26]=[C:25]([O:29][CH:30]([CH3:38])[CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:22]=1[CH:23]=O>CO.C(O)(=O)C>[CH3:17][N:15]([CH3:16])[CH2:14][CH2:13][N:6]1[C:5](=[O:18])[C:4]2[CH:3]=[C:2]3[NH:1][C:23]([C:22]4[C:21]([O:20][CH3:19])=[N:28][CH:27]=[CH:26][C:25]=4[O:29][CH:30]([CH3:38])[CH2:31][C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)=[N:11][C:10]3=[CH:9][C:8]=2[C:7]1=[O:12]

Komponenten

5

Edukt 2

HCID 666864925,6-Diamino-2-(2-(dimethylamino)ethyl)isoindoline-1,3-dioneHCID 86663225HCID 86663225, Verbindung

Produkt 1

HCID 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)-dioneAusbeute 69,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 887MethanolLösungsmittel

Versuchsvorschrift

5,6-Diamino-2-(2-(dimethylamino)ethyl)isoindoline-1,3-dione (0.47 g, 1.88 mmol) was dissolved in MeOH (30 mL) and acetic acid (10 mL). 2-Methoxy-4-((1-phenylpropan-2-yl)oxy)nicotinaldehyde (0.51 g, 1.88 mmol) was added under air at rt. The reaction mixture was stirred at rt under air overnight. The volatile was removed. The residue was subjected to column chromatography (silica-gel, CH2Cl2/MeOH=17/3 v/v) to give a white solid product, 0.65 g, 69.2% yield. MS: 500.3 [M+H]+. 1H-NMR (DMSO-d6, 500 MHz): δ 13.23 (s, 1H), 8.20 (d, 1H, J=6.0 Hz), 8.12 (s, 1H), 7.95 (s, 1H), 7.09-7.07 (m, 1H), 7.11-7.95 (m, 5H), 4.84-4.81 (m, 1H), 3.82 (s, 3H), 3.72 (t, 2H, J=6.5 Hz), 2.78 (d, 2H, J=6.0 Hz), 2.53 (t, 2H, J=6.5 Hz), 2.19 (s, 6H), 1.17 (d, 3H, J=6.0 Hz).

Aufarbeitung

  1. customThe volatile was removed
  2. customto give a white solid product, 0.65 g, 69.2% yield

Quellen und Nachweise

ORD-Eintrag
ord-ab0d4012e8de495da7b0ea3bc715869c
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09273055B2

Notizen zur Reaktion

Wird geladen…