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Acetic Acid → 2-(4-Chloro-2-oxo-1,2-dihydro-pyridin-3-yl)-6-(2-dimethylamino-1-methyl-ethyl)-1H-1,3,6-triaza-s-indacene-5,7-dione

HRID 929133
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 929133
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[N+:11]([O-])=O)[C:7](=[O:14])[N:6]([CH:15]([CH3:20])[CH2:16][N:17]([CH3:19])[CH3:18])[C:5]2=[O:21].[CH3:22][C:23](O)=O.[ClH:26].[CH3:27][OH:28]>O1CCOCC1.O.[Pd]>[Cl:26][C:9]1[CH:10]=[CH:2][NH:1][C:27](=[O:28])[C:23]=1[C:22]1[NH:1][C:2]2[C:10]([N:11]=1)=[CH:9][C:8]1[C:7](=[O:14])[N:6]([CH:15]([CH3:20])[CH2:16][N:17]([CH3:19])[CH3:18])[C:5](=[O:21])[C:4]=1[CH:3]=2
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 887MethanolHCID 667934325-Amino-2-(2-dimethylamino-1-methyl-ethyl)-6-nitro-isoindole-1,3-dione

Produkt 1

HCID 1363511972-(4-Chloro-2-oxo-1,2-dihydro-pyridin-3-yl)-6-(2-dimethylamino-1-methyl-ethyl)-1H-1,3,6-triaza-s-indacene-5,7-dioneAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel

3
HCID 23938PalladiumKatalysatorHCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

The mixture of 5-amino-2-(2-dimethylamino-1-methyl-ethyl)-6-nitro-isoindole-1,3-dione (585 mg, 2.0 mmol) and Pd/C (60 mg) in MeOH (95 mL) was stirred under atmospheric H2 for 2.5 h and filtered through Celite. The filtrate was mixed with 4-chloro-2-methoxynicotinic aldehyde (343.2 mg, 2.0 mmol) and HOAc (5 mL), stirred at the room temperature for 62 h, and evaporated under reduced pressure to afford an oil crude which was mixed with HCl in dioxane (4 M, 25 mL) and H2O (2 mL), heated at 70° C. for 1 h and evaporated. The residue was diluted with a mixed solvent of MeOH/DCM (50 mL/50 mL), basified with 28% aqueous NH4OH, and concentrated. Chromatography of the residue with CH2Cl2/MeOH/28% aqueous NH4OH (60:10:1) afforded the title compound (642 mg, 80%). 1H NMR (DMSO-d6) δ 1.39 (d, J=6 Hz, 3H, CH3), 2.14 (s, 6H, 2CH3), 2.29 (m, 1H), 3.04 (m, 1H), 4.40 (m, 1H), 6.59 (d, J=8 Hz, 1H), 7.69 (d, J=8 Hz, 1H), 8.04 (s, 1H), 8.05 (s, 1H); ESI-MS m/z 400.3 (MH+).

Aufarbeitung

  1. filtrationfiltered through Celite
  2. stirringstirred at the room temperature for 62 h
  3. customevaporated under reduced pressure
  4. customto afford an oil crude which
  5. customevaporated
  6. additionThe residue was diluted with a mixed solvent of MeOH/DCM (50 mL/50 mL)
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-b9626e8db0b74f5dabf151fe0f4966e0
Quelldatensatz
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09290503B2

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