Water → 3-chloro-2-hydroxy-5-[3-(2-methoxy-phenyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-benzoic acid

HRID 2388964Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2388964
[Cl:1][C:2]1[C:3]([OH:36])=[C:4]([CH:8]=[C:9]([C:11]2[CH:12]=[C:13]3[C:19]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=4[O:26][CH3:27])=[N:18][N:17](COCC[Si](C)(C)C)[C:14]3=[N:15][CH:16]=2)[CH:10]=1)[C:5]([OH:7])=[O:6].Cl(O)(=O)(=O)=O.O>C(O)(=O)C>[Cl:1][C:2]1[C:3]([OH:36])=[C:4]([CH:8]=[C:9]([C:11]2[CH:12]=[C:13]3[C:19]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=4[O:26][CH3:27])=[N:18][NH:17][C:14]3=[N:15][CH:16]=2)[CH:10]=1)[C:5]([OH:7])=[O:6]

Komponenten

5

Edukt 3

HCID 962WaterHCID 24247Perchloric AcidHCID 579757203-chloro-2-hydroxy-5-[3-(2-methoxy-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-benzoic acid

Produkt 1

HCID 1784893953-chloro-2-hydroxy-5-[3-(2-methoxy-phenyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-benzoic acidAusbeute 64 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

240 mg (0.46 mmol) of 3-chloro-2-hydroxy-5-[3-(2-methoxy-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-benzoic acid was dissolved in 5 mL of glacial acetic acid. 500 μL of 70% perchloric acid was added and the mixture stirred at ambient temperature for 24 h. 50 mL of water was added and the resulting precipitate filtered off and dried by suction to afford 117 mg (0.29 mmol, 64%) of 3-chloro-2-hydroxy-5-[3-(2-methoxy-phenyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-benzoic acid as a yellow solid. 1H NMR (500 MHz, DMSO-d6) δ 8.83 (d, 1H), 8.34 (d, 1H), 8.14 (d, 1H), 8.07 (d, 1H), 7.66 (dd, 1H), 7.47 (ddd, 1H), 7.22 (d(d), 1H), 7.10 (ddd, 1H), 3.84 (s, 3H), MS: m/z 394.0 (M−H+).

Aufarbeitung

  1. filtrationthe resulting precipitate filtered off
  2. customdried by suction

Quellen und Nachweise

ORD-Eintrag
ord-61719c7c168d487b90813464c044ea76
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08268994B2

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