1-(4-fluorophenyl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-b]pyridine → 2-[4-amino-3-(1H-imidazol-2-yl)pyrazolo[3,4-d]pyrimidin-1-yl]-1-[1-(4-fluorophenyl)-6,7-dihydro-5H-pyrazolo[4,3-b]pyridin-4-yl]ethanone

HRID 710613Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 710613
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH2:16][C:17]([OH:19])=O)[N:9]=[C:10]([C:11]3[NH:12][CH:13]=[CH:14][N:15]=3)[C:3]=12.[F:20][C:21]1[CH:26]=[CH:25][C:24]([N:27]2[C:35]3[CH2:34][CH2:33][CH2:32][NH:31][C:30]=3[CH:29]=[N:28]2)=[CH:23][CH:22]=1>>[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH2:16][C:17]([N:31]3[CH2:32][CH2:33][CH2:34][C:35]4[N:27]([C:24]5[CH:25]=[CH:26][C:21]([F:20])=[CH:22][CH:23]=5)[N:28]=[CH:29][C:30]3=4)=[O:19])[N:9]=[C:10]([C:11]3[NH:15][CH:14]=[CH:13][N:12]=3)[C:3]=12

Komponenten

3

Edukt 2

HCID 679846101-(4-fluorophenyl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-b]pyridineHCID 1360797542-(4-amino-3-(1H-imidazol-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)acetic acid

Produkt 1

HCID 1362523212-[4-amino-3-(1H-imidazol-2-yl)pyrazolo[3,4-d]pyrimidin-1-yl]-1-[1-(4-fluorophenyl)-6,7-dihydro-5H-pyrazolo[4,3-b]pyridin-4-yl]ethanone

Versuchsvorschrift

The compound was prepared from 2-(4-amino-3-(1H-imidazol-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)acetic acid and 1-(4-fluorophenyl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-b]pyridine above using General Method A. The product was purified by reverse phase HPLC (C18 column, acetonitrile-H2O with 0.1% TFA as eluent) to give the desired product as a white solid (6.4 mg). 1H NMR (400 MHz, MeOH-d4) δ 8.35 (s, 1H), 8.15 (s, 1H), 7.54 (m, 2H), 7.27 (m, 4H), 5.70 (s, 2H), 4.00 (m, 2H), 2.91 (t, J=6.2 Hz, 2H), 2.18 (m, 2H); MS: (ES) m/z calculated for C22H20FN10O [M+H]+ 459.18, found 459.1.

Aufarbeitung

  1. customThe product was purified by reverse phase HPLC (C18 column, acetonitrile-H2O with 0.1% TFA as eluent)

Quellen und Nachweise

ORD-Eintrag
ord-59073c32589a4ad59efc957dc9039378
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09181241B2

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