Methanol → 8-(4-(4-(4-Chlorophenyl)phthalazin-1-ylamino)phenoxy)-1,5-naphthyridin-3-ol

HRID 1013780Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1013780
C([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([O:19][C:20]3[CH:25]=[CH:24][C:23]([NH:26][C:27]4[C:36]5[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=5)[C:30]([C:37]5[CH:42]=[CH:41][C:40]([Cl:43])=[CH:39][CH:38]=5)=[N:29][N:28]=4)=[CH:22][CH:21]=3)=[CH:14][CH:15]=[N:16]2)=[N:11][CH:10]=1)C1C=CC=CC=1.CO.[H][H]>C(Cl)Cl.[Pd]>[Cl:43][C:40]1[CH:41]=[CH:42][C:37]([C:30]2[C:31]3[C:36](=[CH:35][CH:34]=[CH:33][CH:32]=3)[C:27]([NH:26][C:23]3[CH:22]=[CH:21][C:20]([O:19][C:13]4[CH:14]=[CH:15][N:16]=[C:17]5[C:12]=4[N:11]=[CH:10][C:9]([OH:8])=[CH:18]5)=[CH:25][CH:24]=3)=[N:28][N:29]=2)=[CH:38][CH:39]=1

Komponenten

6

Edukt 3

HCID 887MethanolHCID 67316920N-(4-(7-(benzyloxy)-1,5-naphthyridin-4-yloxy)phenyl)-4-(4-chlorophenyl)phthalazin-1-amineHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 1359647108-(4-(4-(4-Chlorophenyl)phthalazin-1-ylamino)phenoxy)-1,5-naphthyridin-3-ol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A round bottom flask was charged with N-(4-(7-(benzyloxy)-1,5-naphthyridin-4-yloxy)phenyl)-4-(4-chlorophenyl)phthalazin-1-amine (400 mg, 687 μmol), 10% Pd/C (73.1 mg, 687 μmol) and 3.4 mL MeOH. The flask was fitted with a hydrogen-filled balloon and the mixture was stirred overnight. The mixture was diluted with DCM and filtered through Celite. The filtrate was concentrated and the crude material was purified by reverse phase chromatography, Gilson, 10-90% 0.1% TFA/ACN in water over 15 min to provide 8-(4-(4-(4-chlorophenyl)phthalazin-1-ylamino)phenoxy)-1,5-naphthyridin-3-ol as a light yellow solid. MS: [M+H]=492.

Aufarbeitung

  1. additionfilled balloon
  2. filtrationfiltered through Celite
  3. concentrationThe filtrate was concentrated
  4. customthe crude material was purified by reverse phase chromatography, Gilson, 10-90% 0.1% TFA/ACN in water over 15 min

Quellen und Nachweise

ORD-Eintrag
ord-df39c8a66eee4e99a668a8f16c65b0b2
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07981891B2

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