Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → HCID 178487832, Verbindung

HRID 633819Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 633819
F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.[C:25]([O:29][C:30]([NH:32][C@H:33]1[CH2:38][CH2:37][C@H:36]([CH2:39][CH2:40][C:41]([OH:43])=[O:42])[CH2:35][CH2:34]1)=[O:31])([CH3:28])([CH3:27])[CH3:26].O[C:45]1[CH:46]=[N:47][C:48]2[C:53]([C:54]=1[CH:55]=O)=[CH:52][C:51]([O:57][CH3:58])=[CH:50][CH:49]=2.N1(C2CCCCCCCCCC2)CCCN=CCCCCC1>CN(C)C=O.C(OCC)(=O)C>[C:25]([O:29][C:30](=[O:31])[NH:32][C@H:33]1[CH2:34][CH2:35][C@H:36]([CH2:39][C:40]2[C:41](=[O:43])[O:42][C:45]3[CH:46]=[N:47][C:48]4[C:53]([C:54]=3[CH:55]=2)=[CH:52][C:51]([O:57][CH3:58])=[CH:50][CH:49]=4)[CH2:37][CH2:38]1)([CH3:28])([CH3:26])[CH3:27]

Komponenten

7

Edukt 4

HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 866715273-Hydroxy-6-methoxy-quinoline-4-carbaldehydeHCID 1296629601,8-Diazabicycloundec-7eneHCID 178453888HCID 178453888, Verbindung

Produkt 1

HCID 178487832HCID 178487832, VerbindungAusbeute 34 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (1.04 g, 2.73 mmol, 1.5 eq) is added at room temperature to a stirred solution of 3-(trans-4-tert-butoxycarbonylamino-cyclohexyl)-propionic acid (494 mg, 1.82 mmol, 1.0 eq) and 3-hydroxy-6-methoxy-quinoline-4-carbaldehyde (370 mg, 1.82 mmol, 1.0 eq) in N,N-dimethylformamide (20 mL), followed by 1,8-diazabicycloundec-7-ene (817 μL, 5.46 mmol, 3.0 eq). After 4 hours stirring at 50° C., solvent is evaporated and the residue is extracted with ethyl acetate (3×30 mL) and water (30 mL). The combined organic layers are dried over sodium sulfate, filtered and concentrated to give a crude product that is purified by column chromatography (silica gel, eluent: petroleum ether:ethyl acetate, 5:1 to 2:1, v/v) to afford [trans-4-(6-methoxy-2-oxo-2H-1-oxa-9-aza-phenanthren-3-ylmethyl)-cyclohexyl]-carbamic acid tert-butyl ester as a yellow solid (270 mg, 34% yield).

Aufarbeitung

  1. customsolvent is evaporated
  2. extractionthe residue is extracted with ethyl acetate (3×30 mL) and water (30 mL)
  3. dry with materialThe combined organic layers are dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a crude product that
  7. customis purified by column chromatography (silica gel, eluent

Quellen und Nachweise

ORD-Eintrag
ord-7e8bc1d7a10f4520b1a52dfa792031bd
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09321788B2

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