Diisopropylethylamine → 4-(4-Methylamino-3-nitro-phenoxy)-pyridine-2-carboxylic acid (2-hydroxy-ethyl)-amide

HRID 2070312

Reaktionsgleichung

Reaktionsgleichung von HRID 2070312
[CH3:1][NH:2][C:3]1[CH:18]=[CH:17][C:6]([O:7][C:8]2[CH:13]=[CH:12][N:11]=[C:10]([C:14]([OH:16])=O)[CH:9]=2)=[CH:5][C:4]=1[N+:19]([O-:21])=[O:20].CCN=C=NCCCN(C)C.Cl.C1C=NC2N(O)N=NC=2C=1.C(N(C(C)C)CC)(C)C.CC1(C)[NH:58][CH2:57][CH2:56][O:55]1>C1COCC1.C(OCC)(=O)C>[OH:55][CH2:56][CH2:57][NH:58][C:14]([C:10]1[CH:9]=[C:8]([O:7][C:6]2[CH:17]=[CH:18][C:3]([NH:2][CH3:1])=[C:4]([N+:19]([O-:21])=[O:20])[CH:5]=2)[CH:13]=[CH:12][N:11]=1)=[O:16]

Komponenten

8

Edukt 5

HCID 81531DiisopropylethylamineHCID 181649HOAtHCID 5506972,2-Dimethyl-oxazolidineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 220404974-[4-(Methylamino)-3-nitrophenoxy]pyridine-2-carboxylic acid

Produkt 1

HCID 210373304-(4-Methylamino-3-nitro-phenoxy)-pyridine-2-carboxylic acid (2-hydroxy-ethyl)-amide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a suspension of the 4-(4-methylamino-3-nitro-phenoxy)-pyridine-2-carboxylic acid (1 eq) in dry THF, EDC-HCl (1.2 eq), HOAT (1.2 eq), and diisopropylethylamine (3 eq) were added. The suspension was stirred for 10 minutes whereupon 2,2-dimethyl-oxazolidine (1.1 eq) was added and the solution is allowed to stir overnight. The mixture was then diluted with ethyl acetate and washed with water. The aqueous layer was washed with ethyl acetate, the organic layers combined, dried over MgSO4, filtered, and concentrated. LCMS m/z 333.2 (MH+), tR=2.1 min.

Aufarbeitung

  1. additionwere added
  2. additionwas added
  3. washwashed with water
  4. washThe aqueous layer was washed with ethyl acetate
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-8258e2ed983748f9904c348c7ed09a15
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08299108B2

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