Aniline → 4-methyl-5,6-dihydro-4H-1,3a,6-triaza-as-indacene-8-carboxylic acid phenyl amide

HRID 481070

Reaktionsgleichung

Reaktionsgleichung von HRID 481070
Br.[CH3:2][CH:3]1[CH2:14][C:13]2[NH:12][CH:11]=[C:10]([C:15]([OH:17])=O)[C:9]=2[C:8]2[N:4]1[CH:5]=[CH:6][N:7]=2.[NH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.Cl.CN(C)CCCN=C=NCC.[OH-].[Na+]>O.O1CCOCC1>[C:19]1([NH:18][C:15]([C:10]2[C:9]3[C:8]4[N:4]([CH:5]=[CH:6][N:7]=4)[CH:3]([CH3:2])[CH2:14][C:13]=3[NH:12][CH:11]=2)=[O:17])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Komponenten

7

Edukt 4

HCID 6115AnilineHCID 14798Sodium HydroxideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 697358864-methyl-5,6-dihydro-4H-1,3a,6-triaza-as-indacene-8-carboxylic acid hydrobromide

Produkt 1

HCID 206056014-methyl-5,6-dihydro-4H-1,3a,6-triaza-as-indacene-8-carboxylic acid phenyl amide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A mixture of 4-methyl-5,6-dihydro-4H-1,3a,6-triaza-as-indacene-8-carboxylic acid hydrobromide (25 mg), aniline (12 mg), 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (23 mg), 1,4-dioxane (1.5 mL), and water (1.5 mL) is stirred at room temperature for 4 days. 0.5N sodium hydroxide solution (3 mL) is added and the mixture is extracted with dichloromethane (3×50 mL). The combined organic layers are washed with brine (1×10 mL), dried over magnesium sulfate and concentrated in vacuo. The residue is purified by preparative thin layer chromatography on silica gel, eluting with 5% methanol in dichloromethane, to give 4-methyl-5,6-dihydro-4H-1,3a,6-triaza-as-indacene-8-carboxylic acid phenyl amide, cream solid, 7 mg: LRMS calcd 292.34, found [M+H] 293.2.

Aufarbeitung

  1. extractionthe mixture is extracted with dichloromethane (3×50 mL)
  2. washThe combined organic layers are washed with brine (1×10 mL)
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue is purified by preparative thin layer chromatography on silica gel
  6. washeluting with 5% methanol in dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-3c43f3a41d304ceab4356e261405a58d
Quelldatensatz
uspto-grants-2003_11
Patentnummer
US06653471B2

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