Ammonium Chloride → HCID 68739481, Verbindung

HRID 1752545Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1752545
CON(C)[C:4]([C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][N:10]=[CH:9]2)=[O:5].[CH2:16]([Mg]Cl)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[Cl-].[NH4+]>O1CCCC1>[NH:11]1[C:12]2[C:8](=[CH:7][C:6]([C:4](=[O:5])[CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:14][CH:13]=2)[CH:9]=[N:10]1

Komponenten

5

Edukt 3

HCID 25517Ammonium ChlorideHCID 62814299N-methoxy-N-methyl-1H-indazole-5-carboxamideHCID 178418336HCID 178418336, Verbindung3×

Produkt 1

HCID 68739481HCID 68739481, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A solution of Example 75B (900 mg, 4.39 mmol) in tetrahydrofuran (10 mL) was cooled under argon with an ice bath and treated with a 2M solution of benzyl magnesium chloride in tetrahydrofuran (6.6 mL, 13.16 mmol). The reaction was stirred overnight at room temperature followed by the addition of one more equivalent of benzyl magnesium chloride. The mixture was heated at 70° C. for 9 hours. One more equivalent of benzylmagnesium chloride was added, and the reaction was heated at 70° C. for another 90 minutes and was allowed to cool to room temperature. Aqueous saturated ammonium chloride was added, and the product was extracted with ethyl acetate and purified by silica gel column chromatography using 30% ethyl acetate in hexanes to afford the title compound. MS (ESI+) m/z 237.1 (M+H)+.

Aufarbeitung

  1. temperatureThe mixture was heated at 70° C. for 9 hours
  2. temperaturethe reaction was heated at 70° C. for another 90 minutes
  3. temperatureto cool to room temperature
  4. extractionthe product was extracted with ethyl acetate
  5. custompurified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-2b95b052be0f4267bb0e42db3fe57d8e
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09163007B2

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