Lithium hydroxide, monohydrate → HCID 59618619, Verbindung

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Reaktionsgleichung

[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[NH:12][C:11]3[N:13]=[C:14]([C:17]([F:20])([F:19])[F:18])[CH:15]=[CH:16][C:10]=3[CH2:9][N:8]([S:21]([C:24]3[CH:29]=[CH:28][C:27]([C:30]([CH3:33])([CH3:32])[CH3:31])=[CH:26][CH:25]=3)(=[O:23])=[O:22])[C:7]=2[C:34]=1[CH3:35])#[N:2].O.[OH-].[Li+].[O:39]1CCOCC1.O>CCOC(C)=O>[C:30]([C:27]1[CH:28]=[CH:29][C:24]([S:21]([N:8]2[C:7]3[C:34]([CH3:35])=[C:3]([C:1]([NH2:2])=[O:39])[CH:4]=[CH:5][C:6]=3[NH:12][C:11]3[N:13]=[C:14]([C:17]([F:19])([F:20])[F:18])[CH:15]=[CH:16][C:10]=3[CH2:9]2)(=[O:22])=[O:23])=[CH:25][CH:26]=1)([CH3:31])([CH3:32])[CH3:33]

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

A mixture of 8-cyano-6-[(4-tert-butylphenyl)sulfonyl]-7-methyl-2-(trifluoromethyl)-6,11-dihydro-5H-pyrido[2,3-b][1,5]benzodiazepine (199 mg, 0.398 mmol) and lithium hydroxide monohydrate (50.1 mg, 2.295 mmol) in 1:1 dioxane-water was heated in a microwave reactor for 15 min at 100° C., followed by 30 min at 120° C. The reaction mixture was cooled to room temperature, diluted with EtOAc, and the organic layer was separated, washed with water, brine, dried over MgSO4 and concentrated. The residue was purified via reverse-phase HPLC to provide the title compound. LC/MS: m/e 519.1 (M+H)+. 1H NMR (500 MHz, CD3OD): δ 7.60 (1H, d), 7.35 (1H, d), 7.15 (2H, d), 7.03-7.10 (3H, m), 6.93 (1H, d), 5.19 (1H, d), 4.40 (1H, d), 2.60 (3H, s), 1.25 (9H, s).

Aufarbeitung

temperatureThe reaction mixture was cooled to room temperature
customthe organic layer was separated
washwashed with water, brine
dry with materialdried over MgSO4
concentrationconcentrated
customThe residue was purified via reverse-phase HPLC

Quellen und Nachweise

ORD-Eintrag: ord-a65fcbaff5524da184a02ca947b77e54
Quelldatensatz: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08153626B2

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