Ammonium Chloride → N'-[4-(1H-indol-3-yl)pyrimidin-2-yl]-4-methoxy-6-(4-methylpiperazin-1-yl)benzene-1,3-diamine

HRID 1842724

Reaktionsgleichung

[NH4+].[Cl-].[NH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]2[CH:17]=[CH:16][N:15]=[C:14]([NH:18][C:19]3[CH:24]=[C:23]([N+:25]([O-])=O)[C:22]([N:28]4[CH2:33][CH2:32][N:31]([CH3:34])[CH2:30][CH2:29]4)=[CH:21][C:20]=3[O:35][CH3:36])[N:13]=2)=[CH:4]1>O.C(O)C.[Fe]>[NH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]2[CH:17]=[CH:16][N:15]=[C:14]([NH:18][C:19]3[CH:24]=[C:23]([NH2:25])[C:22]([N:28]4[CH2:33][CH2:32][N:31]([CH3:34])[CH2:30][CH2:29]4)=[CH:21][C:20]=3[O:35][CH3:36])[N:13]=2)=[CH:4]1

Komponenten

Reaktionsbedingungen

Temperatur: 105 °C

Versuchsvorschrift

A solution of NH4Cl (0.021 g, 0.38 mmol) in water (3 mL) was added in one portion to a stirred suspension of 4-(1H-indol-3-yl)-N-[2-methoxy-4-(4-methylpiperazin-1-yl)-5-nitrophenyl]pyrimidin-2-amine (Intermediate 67, 0.235 g, 0.51 mmol) and iron (0.171 g, 3.07 mmol) in ethanol (9 mL) and the mixture was stirred at 105° C. for 18 h. The mixture was then concentrated in vacuo and the resulting residue was dissolved in DMF (20 mL). Purification by ion exchange chromatography, using an SCX column, eluting with 0.35M methanolic ammonia in CH2Cl2 and concentration of the appropriate fractions gave the title compound (0.206 g, 94%) as a yellow solid; m/z: ES+ MH+ 430.51.

Aufarbeitung

concentrationThe mixture was then concentrated in vacuo
dissolutionthe resulting residue was dissolved in DMF (20 mL)
customPurification by ion exchange chromatography
washeluting with 0.35M methanolic ammonia in CH2Cl2 and concentration of the appropriate fractions

Quellen und Nachweise

ORD-Eintrag: ord-488bea28bb164e798bdab266afe93115
Quelldatensatz: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08946235B2

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