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Ethanol, 2-(aminooxy)- → HCID 89451604, Verbindung

HRID 2175154
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2175154
Cl.[O:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:10]=[N:11][C:12]3[C:17]([CH:18]=2)=[CH:16][C:15]([S:19][C:20]2[N:24]4[CH:25]=[C:26]([C:29](=O)[CH3:30])[CH:27]=[CH:28][C:23]4=[N:22][N:21]=2)=[CH:14][CH:13]=3)[CH2:4][CH2:3]1.[NH2:32][O:33][CH2:34][CH2:35][OH:36]>CO.Cl>[OH:36][CH2:35][CH2:34][O:33]/[N:32]=[C:29](/[C:26]1[CH:27]=[CH:28][C:23]2[N:24]([C:20]([S:19][C:15]3[CH:16]=[C:17]4[C:12](=[CH:13][CH:14]=3)[N:11]=[CH:10][C:9]([CH2:8][N:5]3[CH2:6][CH2:7][O:2][CH2:3][CH2:4]3)=[CH:18]4)=[N:21][N:22]=2)[CH:25]=1)\[CH3:30]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 3014186Ethanol, 2-(aminooxy)-HCID 86696281HCID 86696281, Verbindung

Produkt 1

HCID 89451604HCID 89451604, VerbindungAusbeute 54,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidKatalysatorHCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

To a solution of 1-(3-(3-(morpholinomethyl)quinolin-6-ylthio)-[1,2,4]triazolo[4,3-a]pyridin-6-yl)ethanone hydrochloride (79.3) (23 mg, 0.047 mmol) and 2-(aminooxy)ethanol (10.80 mg, 0.140 mmol) in MeOH (5 ml) was added 2 drops of HCl (2 N) by a 1-ml syringe to reach pH about 3 and the mixture was stirred in a sealed tube at 85° C. for 3 h. The mixture was evaporated to dryness and the residue was dissolved in water. The solution was neutralized by adding solid NaHCO3 until pH reached 9, then extracted by DCM (3×). The combined organic layers were washed by water again, dried over Na2SO4, filtered and evaporated. The residue was purified by preparative base HPLC (gradient eluent NB from 20/80 to 95/5. mobile phase A: NH4OH/CH3CN 0.04%; mobile phase B: NH4OH/H2O 0.04%). The desired fractions were collected, evaporated by BUCHI under 30 mbar at 35° C. to remove CH3CN. The remained solution was lyophilized to afford the title compound (12.2 mg, yield 54.2%).

Aufarbeitung

  1. customThe mixture was evaporated to dryness
  2. dissolutionthe residue was dissolved in water
  3. additionby adding solid NaHCO3 until pH
  4. extractionextracted by DCM (3×)
  5. washThe combined organic layers were washed by water again
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified by preparative base HPLC (gradient eluent NB from 20/80 to 95/5. mobile phase A: NH4OH/CH3CN 0.04%; mobile phase B: NH4OH/H2O 0.04%)
  10. customThe desired fractions were collected
  11. customevaporated by BUCHI under 30 mbar at 35° C.
  12. customto remove CH3CN

Quellen und Nachweise

ORD-Eintrag
ord-ccd8028640ae46a9a20111f4c1bb0550
Quelldatensatz
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09062045B2

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