Acetic Acid → HCID 178434031, Verbindung

HRID 253262

Reaktionsgleichung

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

Komponenten

Reaktionsbedingungen

Temperatur: 120 °C

Versuchsvorschrift

To 3-[5-amino-1-(1,1-dimethylethyl)-3-methyl-1H-pyrazol-4-yl]-2,5-difluorophenol (0.050 g, 0.178 mmol) and 3-chloro-4-[(phenylmethyl)oxy]benzaldehyde (0.044 g, 0.178 mmol) was added acetic acid (1 mL). The mixture was stirred at 120° C. for 4.5 h and then concentrated in vacuo to afford a residue which was co-evaporated with EtOH (2×) to afford a film which was purified by column chromatography (ether-dichloromethane 1:20) to afford 5-{3-chloro-4-[(phenylmethyl)oxy]phenyl}-3-(1,1-dimethylethyl)-6,9-difluoro-1-methyl-3H-pyrazolo[3,4-c]isoquinolin-8-ol as a light brown foam (0.042 g, 0.083 mmol, 47% yield). 1H NMR (400 MHz, CDCl3): 7.63 (t, 1H), 7.55-7.51 (m, 2H), 7.46-7.34 (m, 5H), 7.06 (d, 1H), 6.86 (dd, 1H), 5.25 (s, 2H), 2.81 (d, 3H), 1.84 (s, 9H); MS (EI) for C28H24ClF2N3O2: 508 (MH+).

Aufarbeitung

concentrationconcentrated in vacuo
customto afford a residue which
customto afford a film which
customwas purified by column chromatography (ether-dichloromethane 1:20)

Quellen und Nachweise

ORD-Eintrag: ord-cd83d01eadfd403c8cec37140c9549a4
Quelldatensatz: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07872014B2

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