Isopropanol → 6-isopropoxy-N-(3-Chloro-4-methoxyphenyl)-N'-cycloheptyl-[1,3,5]triazine-2,4-diamine

HRID 915148

Reaktionsgleichung

[CH:1]([OH:4])([CH3:3])[CH3:2].[OH-].[Na+].Cl[C:8]1[N:13]=[C:12]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([Cl:23])[CH:16]=2)[N:11]=[C:10]([NH:24][CH:25]2[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)[N:9]=1>C1C=CC=CC=1>[Cl:23][C:17]1[CH:16]=[C:15]([NH:14][C:12]2[N:11]=[C:10]([NH:24][CH:25]3[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]3)[N:9]=[C:8]([O:4][CH:1]([CH3:3])[CH3:2])[N:13]=2)[CH:20]=[CH:19][C:18]=1[O:21][CH3:22]

Komponenten

Reaktionsbedingungen

Temperatur: 25 °C

Versuchsvorschrift

A mixture of isopropanol (2 mL) and sodium hydroxide (95 mg, 2.27 mmol) in benzene (10 mL) was heated to reflux for 2 hours with stirring under nitrogen atmosphere and then cooled to 25° C. followed by the addition of compound 133 (0.3 g, 0.78 mmol) at same temperature. The mixture was heated to reflux for 6 hours, concentrated under vacuum and diluted with water (10 mL). The precipitated solid was filtered off and purified by column chromatography (1-2% MeOH—CHCl3) to afford the title compound E21 as an off-white solid (0.30 g, 94%). mp 136-138° C.; HPLC: Inertsil ODS 3V (250×4.6 mm) 5 microns [solvent A=0.01 M KH2PO4 (pH 7.0); solvent B=CH3CN], Gradient elution program: T/% B=0/60, 10/60, 25/80, 40/80, 45/60, 50/60; 268 nm, Rt 30.06 min, 98.78% purity; MS (CI): m/z 406 (M+H, 100).

Aufarbeitung

temperaturewas heated
temperatureto reflux for 2 hours
temperatureThe mixture was heated
temperatureto reflux for 6 hours
concentrationconcentrated under vacuum
additiondiluted with water (10 mL)
filtrationThe precipitated solid was filtered off
custompurified by column chromatography (1-2% MeOH—CHCl3)

Quellen und Nachweise

ORD-Eintrag: ord-79d60ba84ee8493ba63b48526f8d98f2
Quelldatensatz: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07265114B2

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