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1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 2,6-Diaminopyridine-3-carboxamide

HRID 1927227
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1927227
[NH2:1][C:2]1[N:10]=[C:9]([NH2:11])[CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].CC[N:14]=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[Cl-].[NH4+].C(N(C(C)C)CC)(C)C>O.CS(C)=O>[NH2:1][C:2]1[N:10]=[C:9]([NH2:11])[CH:8]=[CH:7][C:3]=1[C:4]([NH2:14])=[O:5]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 25517Ammonium ChlorideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 189772452,6-Diaminonicotinic acid

Produkt 1

HCID 204748872,6-Diaminopyridine-3-carboxamideAusbeute 73,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

2,6-Diaminonicotinic acid (1.5 g), WSC (2.8 g), HOBt (2.0 g), ammonium chloride (1.6 g), diisopropylethylamine (7.6 g), and DMSO (45 mL) were stirred for 15 hours at room temperature. Water was added to the reaction solution, which was then extracted with ethyl acetate. The organic layer was concentrated and purified by silica gel chromatography (ethyl acetate, then ethyl acetate:methanol=4:1). The organic layer thus obtained was concentrated and purified by NH silica gel column chromatography (ethyl acetate). Ethyl acetate and hexane were added to the residue thus obtained, and the solids were filtered off to obtain the titled compound (1.1 g).

Aufarbeitung

  1. extractionwas then extracted with ethyl acetate
  2. concentrationThe organic layer was concentrated
  3. custompurified by silica gel chromatography (ethyl acetate
  4. customThe organic layer thus obtained
  5. concentrationwas concentrated
  6. custompurified by NH silica gel column chromatography (ethyl acetate)
  7. additionEthyl acetate and hexane were added to the residue
  8. customthus obtained
  9. filtrationthe solids were filtered off

Quellen und Nachweise

ORD-Eintrag
ord-01050031bd7d42c6ae7a0e2674aca124
Quelldatensatz
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08183264B2

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