tert-butyl 3-{[5-chloro-4-(2,5-dichloro-3-cyanophenoxy)-1H-1,2,3-benzotriazol-1-yl]methyl}-1H-pyrazolo[3,4-b]pyridine-1-carboxylate → HCID 178509925, Verbindung

HRID 505552Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 505552
[Cl:1][C:2]1[CH:27]=[CH:26][C:5]2[N:6]([CH2:9][C:10]3[C:18]4[C:13](=[N:14][CH:15]=[CH:16][CH:17]=4)[N:12](C(OC(C)(C)C)=O)[N:11]=3)[N:7]=[N:8][C:4]=2[C:3]=1[O:28][C:29]1[CH:34]=[C:33]([Cl:35])[CH:32]=[C:31]([C:36]#[N:37])[C:30]=1[Cl:38]>C(O)(C(F)(F)F)=O>[Cl:38][C:30]1[C:29]([O:28][C:3]2[C:4]3[N:8]=[N:7][N:6]([CH2:9][C:10]4[C:18]5[C:13](=[N:14][CH:15]=[CH:16][CH:17]=5)[NH:12][N:11]=4)[C:5]=3[CH:26]=[CH:27][C:2]=2[Cl:1])=[CH:34][C:33]([Cl:35])=[CH:32][C:31]=1[C:36]#[N:37]

Komponenten

3

Edukt 1

HCID 68428123tert-butyl 3-{[5-chloro-4-(2,5-dichloro-3-cyanophenoxy)-1H-1,2,3-benzotriazol-1-yl]methyl}-1H-pyrazolo[3,4-b]pyridine-1-carboxylate

Produkt 1

HCID 178509925HCID 178509925, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6422Trifluoroacetic acidLösungsmittel

Versuchsvorschrift

tert-Butyl 3-{[5-chloro-4-(2,5-dichloro-3-cyanophenoxy)-1H-1,2,3-benzotriazol-1-yl]methyl}-1H-pyrazolo[3,4-b]pyridine-1-carboxylate (569 mg, 0.997 mmol) was dissolved in TFA (5 mL). After 20 minutes, the reaction mixture was concentrated under reduced pressure, and the resulting residue was purified by reverse phase chromatography eluting with 30-95% MeCN/H2O+0.1% TFA. Product fractions concentrated under reduced pressure to yield the title compound. 1H NMR (DMSO-d6) δ 8.53 (dd, J=4.4 Hz, J=1.6 Hz, 1H), 8.14 (dd, J=8.0 Hz, J=1.5 Hz, 1H), 8.04 (d, J=0.6 Hz, 1H), 7.89 (d, J=8.9 Hz, 1H), 7.79 (d, J=8.9 Hz, 1H), 7.44 (d, J=0.6 Hz, 1H), 7.21 (dd, J=8.0 Hz, J=4.5 Hz, 1H), 6.38 (d, 2H). HRMS (M+1)=470.0076

Aufarbeitung

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. customthe resulting residue was purified by reverse phase chromatography
  3. washeluting with 30-95% MeCN/H2O+0.1% TFA
  4. concentrationProduct fractions concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-d7d95ea8aad9476aad0cdc83ca4efebe
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07781454B2

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