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Water → 2-Aminocarbonylamino-6-azidomethylindole-3-carboxamide

HRID 216642
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 216642
C1(P([N:15]=[N+:16]=[N-:17])(C2C=CC=CC=2)=O)C=CC=CC=1.N12CCCN=C1CCCCC2.[NH2:29][C:30]([NH:32][C:33]1[NH:34][C:35]2[C:40]([C:41]=1[C:42]([NH2:44])=[O:43])=[CH:39][CH:38]=[C:37]([CH2:45]O)[CH:36]=2)=[O:31].O>O1CCCC1>[NH2:29][C:30]([NH:32][C:33]1[NH:34][C:35]2[C:40]([C:41]=1[C:42]([NH2:44])=[O:43])=[CH:39][CH:38]=[C:37]([CH2:45][N:15]=[N+:16]=[N-:17])[CH:36]=2)=[O:31]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 962WaterHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 199401P,P-Diphenylphosphinic azideHCID 249894282-Aminocarbonylamino-6-hydroxymethylindole-3-carboxamide2×

Produkt 1

HCID 591899312-Aminocarbonylamino-6-azidomethylindole-3-carboxamideAusbeute 11,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Diphenylphosphoryl azide (42 μL, 0.19 mmol) and 1,8-diazabicyclo[5.4.0]undec-7-ene (29 μL, 0.19 mmol) were added to a solution of 2-aminocarbonylamino-6-hydroxymethylindole-3-carboxamide (Compound 16-1, 40 mg, 0.16 mmol) in anhydrous tetrahydrofuran (5 mL) under ice-cooling, the mixture was stirred at room temperature overnight. Water (10 mL) was added to the reaction mixture, and the whole was extracted with ethyl acetate (10 mL). The organic layer was washed with brine (20 mL) and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography to give the title compound (5.0 mg) as a yellow solid (yield 11%).

Aufarbeitung

  1. temperaturecooling
  2. extractionthe whole was extracted with ethyl acetate (10 mL)
  3. washThe organic layer was washed with brine (20 mL)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-44e89feb11b249e19d66e80b05704a5b
Quelldatensatz
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08193237B2

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