N1-{4-[4-amino-1-(4-hydroxy-2-cyclopentenyl)-1H-pyrazolo[3,4-d]pyrimidin-3-yl]-2-methoxyphenyl}-2-fluoro-4-trifluoromethylbenzamide → N1-{4-[4-amino-1-(3-hydroxycyclopentyl)-1H-pyrazolo[3,4-d]pyrimidin-3-yl]-2-methoxyphenyl}-2-fluoro-4-trifluoromethylbenzamide

HRID 2056049Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2056049
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH:33]3[CH2:37][CH:36]([OH:38])[CH:35]=[CH:34]3)[N:9]=[C:10]([C:11]3[CH:16]=[CH:15][C:14]([NH:17][C:18](=[O:30])[C:19]4[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][C:20]=4[F:29])=[C:13]([O:31][CH3:32])[CH:12]=3)[C:3]=12.[H][H]>[Pd].C(O)C>[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH:33]3[CH2:34][CH2:35][CH:36]([OH:38])[CH2:37]3)[N:9]=[C:10]([C:11]3[CH:16]=[CH:15][C:14]([NH:17][C:18](=[O:30])[C:19]4[CH:24]=[CH:23][C:22]([C:25]([F:27])([F:28])[F:26])=[CH:21][C:20]=4[F:29])=[C:13]([O:31][CH3:32])[CH:12]=3)[C:3]=12

Komponenten

5

Edukt 2

HCID 22347104N1-{4-[4-amino-1-(4-hydroxy-2-cyclopentenyl)-1H-pyrazolo[3,4-d]pyrimidin-3-yl]-2-methoxyphenyl}-2-fluoro-4-trifluoromethylbenzamideHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 22346909N1-{4-[4-amino-1-(3-hydroxycyclopentyl)-1H-pyrazolo[3,4-d]pyrimidin-3-yl]-2-methoxyphenyl}-2-fluoro-4-trifluoromethylbenzamideAusbeute 68,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of N1-{4-[4-amino-1-(4-hydroxy-2-cyclopentenyl)-1H-pyrazolo[3,4-d]pyrimidin-3-yl]-2-methoxyphenyl}-2-fluoro-4-trifluoromethylbenzamide (0.10 g, 0.19 mmol) and 10% palladium on carbon (0.03 g) in ethanol (10 mL) was stirred at ambient temperature under one atmosphere of hydrogen overnight. The mixture was filtered and the filtrate was purified by preparative HPLC to yield N1-{4-[4-amino-1-(3-hydroxycyclopentyl)-1H-pyrazolo[3,4-d]pyrimidin-3-yl]-2-methoxyphenyl}-2-fluoro-4-trifluoromethylbenzamide (0.07 g, 0.13 mmol) as a white sold: 1H NMR (DMSO-d6, 400 MHz) δ 9.91 (dd, 1H), 8.31(d, 1H), 8.24 (s, 1H), 8.00 (t, 1H), 7.89 (d, 1H), 7.75 (d, 1H), 7.34 (s, 1H), 7.30 (d, 1H), 6.90 (br, 2H), 5.17 (m, 1H), 4.97 (m, 1H), 4.22 (m, 1H), 3.94 (s, 3H), 1.79-2.41 (m, 6H); MS: MH+ 531.

Aufarbeitung

  1. filtrationThe mixture was filtered
  2. customthe filtrate was purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-e5c0fd25923946bc8ea5d1c3f1f182e6
Quelldatensatz
uspto-grants-2008_02
Patentnummer
US07332497B2

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