Cesium carbonate → (1R,2S)-1-(1-(4-fluorophenyl)-1H-indazol-5-yloxy)-1-(naphthalen-2-yl)propan-2-amine hydrochloride

HRID 13023

Reaktionsgleichung

Reaktionsgleichung von HRID 13023
[ClH:1].[NH2:2][C@@H:3]([CH3:16])[C@@H:4]([C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=1)[OH:5].[F:17][C:18]1[CH:23]=[CH:22][C:21]([N:24]2[C:32]3[C:27](=[CH:28][C:29](I)=[CH:30][CH:31]=3)[CH:26]=[N:25]2)=[CH:20][CH:19]=1.[C:34](=O)([O-])[O-:35].[Cs+].[Cs+]>C(#N)CCC.[Cu]I>[ClH:1].[F:17][C:18]1[CH:19]=[CH:20][C:21]([N:24]2[C:32]3[C:27](=[CH:28][C:29]([O:5][C@H:4]([C:6]4[CH:15]=[CH:14][C:13]5[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=5)[CH:7]=4)[C@@H:3]([NH2:2])[CH3:16])=[CH:30][CH:31]=3)[CH:26]=[N:25]2)=[CH:22][CH:23]=1.[C:13]([O:35][CH3:34])([CH3:12])([CH3:8])[CH3:14].[ClH:1]

Komponenten

7

Edukt 3

HCID 10796Cesium carbonateHCID 592511281-(4-fluorophenyl)-5-iodo-1H-indazoleHCID 66812834(1R,2S)-2-amino-1-(naphthalen-2-yl)propan-1-ol hydrochloride

Produkt 2

HCID 66812502(1R,2S)-1-(1-(4-fluorophenyl)-1H-indazol-5-yloxy)-1-(naphthalen-2-yl)propan-2-amine hydrochlorideHCID 86756611tert-butylmethylether HCl

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 8008ButyronitrileLösungsmittel

Versuchsvorschrift

The subtitle compound was prepared analogous to the method described in Example 19 (step 19a). (1R,2S)-2-amino-1-(naphthalen-2-yl)propan-1-ol hydrochloride (238 mg, 1.00 mmol), 1-(4-fluorophenyl)-5-iodo-1H-indazole (406 mg, 1.20 mmol), Cesium carbonate (979 mg, 3.00 mmol) and copper(I) iodide (38.1 mg, 0.20 mmol) in Butyronitrile (3 mL) was heated for 19 h at +125° C. in a sealed reactiontube flushed with Argon. After final purification by HPLC the obtained material was isolated as a brownish coloured hydrochloride salt from tert-butylmethylether/HCl.

Aufarbeitung

  1. customflushed with Argon
  2. customAfter final purification by HPLC the obtained material

Quellen und Nachweise

ORD-Eintrag
ord-947f88f0e9fb4cf3906cb5ff60185fa8
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07728030B2

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