Ammonium Hydroxide → HCID 58550623, Verbindung

HRID 1890710Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1890710
[O:1]=[C:2]1[N:10]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C@@:3]21[CH2:34][C:21]1=[N:22][C:23]3[CH:24]=[CH:25][C:26]([C:30](NN)=[O:31])=[CH:27][C:28]=3[CH:29]=[C:20]1[CH2:19]2.[NH4+].[OH-]>C(Cl)Cl.O.[Fe-3](C#N)(C#N)(C#N)(C#N)(C#N)C#N.[K+].[K+].[K+]>[O:1]=[C:2]1[N:10]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:16])([CH3:17])[CH3:18])[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C@@:3]21[CH2:34][C:21]1=[N:22][C:23]3[CH:24]=[CH:25][C:26]([CH:30]=[O:31])=[CH:27][C:28]=3[CH:29]=[C:20]1[CH2:19]2

Komponenten

6

Edukt 2

HCID 14923Ammonium HydroxideHCID 58550577HCID 58550577, Verbindung

Produkt 1

HCID 58550623HCID 58550623, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178511488HCID 178511488, VerbindungKatalysatorHCID 962WaterLösungsmittel2×HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a rapidly stirred solution of (2S)-2′-oxo-1′-{[2-(trimethylsilyl)eth-oxy]methyl}-1,1′,2′,3-tetrahydrospiro[cyclopenta[b]quinoline-2,3′-pyrrolo[2,3-b]pyridine]-7-carbohydrazide from Step H (317 mg, 0.667 mmol) in DCM (6.8 mL) was added water (2.7 mL) plus concentrated aqueous NH4OH (0.6 mL) and lastly potassium ferricyanide (549 mg, 1.67 mmol). After 4.5 hours the reaction was diluted with water (20 mL) and DCM (40 mL). The aqueous layer was extracted once with DCM (20 mL). The combined organics were washed successively with water then half-saturated brine and then dried over sodium sulfate. The organics were then filtered, concentrated in vacuo, and applied to a silica gel column for purification, eluting with a gradient of CH2Cl2:MeOH—99:1 to 90:10. Clean product-containing fractions were pooled and concentrated in vacuo to give the title compound. MS: m/z=446 (M+1).

Aufarbeitung

  1. extractionThe aqueous layer was extracted once with DCM (20 mL)
  2. washThe combined organics were washed successively with water
  3. dry with materialhalf-saturated brine and then dried over sodium sulfate
  4. filtrationThe organics were then filtered
  5. concentrationconcentrated in vacuo
  6. customapplied to a silica gel column for purification
  7. washeluting with a gradient of CH2Cl2
  8. additionClean product-containing fractions
  9. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-fac5351aa7804aa2bbc8b30e6fc12639
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08507477B2

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