Phthalic Anhydride → 2-({3-[2-(4-Fluorophenyl)-3-(methylcarbamoyl)-2H-indazol-6-yl]phenyl}carbamoyl)benzoic acid

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Reaktionsgleichung

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

Komponenten

Reaktionsbedingungen

Temperatur: 70 °C

Versuchsvorschrift

To a solution of Compound (16) (10 mg, 0.03 mmol) in ACN (3 mL) was added phthalic anhydride (8.2 mg, 0.06 mmol) and the reaction mixture was heated to 70° C. and stirred for 15 h. The reaction mixture was then cooled to RT and the resulting precipitate was collected by filtration. The residue was washed with cold ACN (5 mL) to afford Compound (17) as an off-white amorphous solid (7.83 mg, 55%). ESI-MS m/z calculated for [M+H]+: 509.15; found: 509.08. 1H NMR (400 MHz, d6-DMSO) δ 13.07 (brs, 1H), 10.47 (s, 1H), 8.77-8.71 (m, 1H), 7.99-7.87 (m, 3H), 7.77-7.38 (m, 12H), 2.85 (d, J=4.5 Hz, 3H).

Aufarbeitung

temperatureThe reaction mixture was then cooled to RT
filtrationthe resulting precipitate was collected by filtration
washThe residue was washed with cold ACN (5 mL)

Quellen und Nachweise

ORD-Eintrag: ord-22fcd8d8baab48c899bd0180090912b8
Quelldatensatz: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08546389B2

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