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

HRID 1042921Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1042921
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-17c72cea16c94f8f95064f53301439ac
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08557816B2

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