Sodium Hydroxide → 4-methyl-3-(9H-pyrimido[4,5-b]indol-7-yl)aniline

HRID 77699

Reaktionsgleichung

[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8]C(=O)C2C=CC=C(C(F)(F)F)C=2)=[CH:4][C:3]=1[C:21]1[CH:29]=[C:28]2[C:24]([C:25]3[CH:33]=[N:32][CH:31]=[N:30][C:26]=3[NH:27]2)=[CH:23][CH:22]=1.O1CCOCC1.[OH-].[Na+]>O>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[CH:4][C:3]=1[C:21]1[CH:29]=[C:28]2[C:24]([C:25]3[CH:33]=[N:32][CH:31]=[N:30][C:26]=3[NH:27]2)=[CH:23][CH:22]=1

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

To N-[4-methyl-3-(9H-pyrimido[4,5-b]indol-7-yl)phenyl]-3-(trifluoromethyl)benzamide (442 mg, 0.990 mmol) was added 1,4-dioxane (2.0 mL) and water (2.0 mL) and sodium hydroxide (790 mg, 19.8 mmol). The resulting mixture was heated to 100° C. until LCMS indicated complete hydrolysis, typically 14-16 hours. The reaction was cooled to ambient temperature and the solvents were removed by evaporation. The residue was washed with water and the remaining solid was recovered by filtration, washed with additional water, and dried under reduced pressure to give the product (207 mg, 76%). 1H NMR (300 MHz, DMSO): δ 9.42 (s, 1H), 8.90 (s, 1H), 8.22 (d, 1H), 7.39 (s, 1H), 7.23 (d, 1H), 6.94 (d, 1H), 6.52 (m, 2H), 4.95 (s, 2H), 2.08 (s, 3H). MS (EI) m/z=275 (M+H).

Aufarbeitung

customhydrolysis, typically 14-16 hours
temperatureThe reaction was cooled to ambient temperature
customthe solvents were removed by evaporation
washThe residue was washed with water
filtrationthe remaining solid was recovered by filtration
washwashed with additional water
customdried under reduced pressure

Quellen und Nachweise

ORD-Eintrag: ord-deefaab6b7e44388a2959ca7d84573f4
Quelldatensatz: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08841318B2

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