Hydrogen Bromide → HCID 59278150, Verbindung

HRID 559660Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 559660
[CH3:1][S:2]([C:5]1[CH:10]=[C:9]([CH2:11][NH:12][C:13]([C:15]2[C:16]3[CH:23]=[N:22][N:21]([C:24]4[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=4)[C:17]=3[CH:18]=[N:19][CH:20]=2)=[O:14])[CH:8]=[C:7]([O:31]C)[N:6]=1)(=[O:4])=[O:3].Br>C(O)(=O)C>[CH3:1][S:2]([C:5]1[NH:6][C:7](=[O:31])[CH:8]=[C:9]([CH2:11][NH:12][C:13]([C:15]2[C:16]3[CH:23]=[N:22][N:21]([C:24]4[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=4)[C:17]=3[CH:18]=[N:19][CH:20]=2)=[O:14])[CH:10]=1)(=[O:4])=[O:3]

Komponenten

4

Edukt 2

HCID 260Hydrogen BromideHCID 59278193HCID 59278193, Verbindung

Produkt 1

HCID 59278150HCID 59278150, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

To a solution of 1-(4-fluorophenyl)-1H-pyrazolo[3,4-c]pyridine-4-carboxylic acid (2-methanesulfonyl-6-methoxy-pyridin-4-ylmethyl)-amide (58 mg, 0.13 mmol) in acetic acid (5 mL) was added 48% aqueous HBr (3 mL). After 16 hours, HPLC-MS indicated partial conversion to the desired product. The mixture was then warmed at 60° C. After 5 hours, the mixture was cooled to room temperature, diluted with water (25 mL) and extracted with EtOAc (3×20 mL). The combined organic layers were washed with saturated aqueous sodium bicarbonate (4×20 mL), brine (20 mL), dried over sodium sulfate and concentrated in vacuo. The residue was purified by silica gel chromatography using a gradient of 0-20% MeOH in EtOAc to afford the title compound as a pale yellow crystalline solid.

Quellen und Nachweise

ORD-Eintrag
ord-21a9bb4bdec64b138d11a848da924c80
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08063065B2

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